All 229 of Taylor Swift’s Songs, Ranked

Taylor Swift the celebrity is such a magnet for attention, she can distract from TAYLOR SWIFT THE artist. But Swift was a songwriter before she was a star, and she’ll be a songwriter long after she graduates from that racket. It’s in her music where she’s made her mark on history — as a performer, record-crafter, guitar hero and all-around pop mastermind, with songs that can leave you breathless or with a nasty scar. She was soaring on the level of the all-time greats before she was old enough to rent a car, with the crafty guile of a Carole King and the reckless heart of a Paul Westerberg — and she hasn’t exactly slowed down since then.

So with all due respect to Taylor the myth, the icon, the red-carpet tabloid staple, let’s celebrate the real Taylor — the songwriter she was born to be. Let’s break it down: all 229 tunes, counted from the bottom to the top. The hits, the flops, the deep cuts, the covers, from her raw 2006 debut as a teen country ingenue right up to Midnights

Every fan would compile a different list—that’s the beauty of it. She’s got at least 5 or 6 dozen songs that seem to belong in her Top Ten. But they’re not ranked by popularity, sales or supposed celebrity quotient — just the level of Taylor genius on display, from the perspective of a fan who generally does not give a rat’s nads who the songs are “really” about. All that matters is whether they’re about you and me. (I guarantee you are a more fascinating human than the Twilight guy, though I’m probably not.)

Since Taylor loves nothing more than causing chaos in our lives, she’s re-recording her albums, including the outtakes she left in the vault before. So far, she’s up to Fearless and Red. For the Taylor’s Version remakes, both versions count as the same song. It’s a tribute to her fierce creative energy — in the past couple years she’s released an avalanche of new music, with more on the way. God help us all.

Sister Tay may be the last true rock star on the planet, making brilliant moves (or catastrophic gaffes, because that’s what rock stars do). These are the songs that sum up her wit, her empathy, her flair for emotional excess, her girls-to-the-front bravado, her urge to ransack every corner of pop history, her determination to turn any chorus into a ridiculous spectacle. So let’s step back from the image and pay homage to her one-of-a-kind songbook — because the weirdest and most fascinating thing about Taylor Swift will always be her music.

229. “Bad Blood” (2014)

Melodically parched, lyrically unfinished, rhythmically clunky – this was a mighty strange pick for a single from an album as loaded as 1989. There are a million things Taylor has in common with Paul McCartney – one is that celebrity grievances tend to sound like a penny-ante waste of their time, even when they’re totally understandable (unless you’re a fan of Macca’s “Dear Boy,” where John Lennon is his Katy Perry). The single remix is improved by Kendrick Lamar – but he wasn’t saving his A-game for this one.

Best line: “Band-Aids don’t fix bullet holes.”

228. “Santa Baby” (2007)

Yes, she made a Christmas album, which is full of contenders for the basement of this list. But an oldie about a gold digger wooing Little Saint Nick was perhaps a dubious pick for a singer still in her teens.

Best line: “I’ve been an awful good girl.”

227. “A Place in This World” (2006)

Apprentice work from the debut, when she was still learning the ropes as a country songwriter. Yet, the seeds of greatness are already there. Historical significance: This was the song where Tay discovered rain imagery, which in her hands was the equivalent of Sir Isaac Newton inventing calculus.

Best line: “I’ll be strong/I’ll be wrong/Oh, but life goes on.”

226. “Christmas Must Be Something More” (2007)

A hymn about how Jesus is the reason for the season, with the hook, “So here’s to the birthday boy who saved our lives.” Unlike most boys Swift sings about, Jesus didn’t comment publicly.

Best line: “What would happen if God never let it snow?”

225. “I’m Only Me When I’m With You” (2006)

Could there be a less Swiftian sentiment? For better or worse, this girl is always herself. That’s kinda the point.

Best line: “I’m only up when you’re not down/Don’t wanna fly if you’re still on the ground.”

224. “Two Is Better Than One,” With Boys Like Girls (2009)

A long, long, very long duet with former Good Charlotte and Fall Out Boy tourmates Boys Like Girls, who are either from London or Nashville (they seem to switch accents at random). For some reason, they decided to delay her entrance until a minute into the song, arguably the worst decision in the history of decisions.

Best line: “You already got me coming…undone.”

223. “Silent Night” (2007)

This bizarre version manages to miss almost every single note in the melody. They sure were in a rush to get this Christmas album out.

Best line: “Shepherds quake at the sight.”

222. “Macavity” (2019

This one will be tough to explain to future generations, but here goes: So they made this Hollywood movie out of the Broadway musical Cats. Full of magic, furry, singing cats. So much fur. So much magic. Taylor plus felines — it should add up to classic cinema, right? Not quite.

Best line: “Macavity’s a mystery cat / He’s called the Hidden Paw.”

221. “Both of Us,” With B.o.B (2012)

Nice try at remaking “Airplanes,” but that Hayley Williams lightning does not strike twice.

Best line: “Your money’s all gone, and you lose your whip.”

220. “The Last Time,” With Gary Lightbody (2012)

Her duet with the guy from Snow Patrol. Unfortunately, their voices don’t mesh at all – what, is he auditioning for a Spandau Ballet tribute band? The funny moment is the très Eighties synth-horn blurp at the three-minute mark.

Best line: “This is the last time I’m asking you this/Put my name at the top of your list.”

219. “ME!” With Brendon Urie (2019)

One of those beloved Taylor traditions: the Lead Single That Reveals Absolutely Nothing About the New Album. And for the second time in a row, it’s the weakest track by a mile. Honestly, Taylor would have released “Maxwell’s Silver Hammer” as the first single from Abbey damn Road. “ME!” is her only song title with an exclamation point, an oddity for this most !!! of singers. Even Brendon Urie sounds squeamish, and he’s the guy who once released a song called “Folkin’ Around.” As we now know, she had “Cruel Summer” in the can, but opted not to make it the summer jam of 2019 because she decided to release “ME!” instead, a decision that will be studied by Swiftian scholars for years to come.

Best line: “Hey kids, spelling is fun!”

218. “The Outside” (2006)

Still a rookie, still learning, still trying to get away with “read between the lines” and “the road less traveled by” in the same verse.

Best line: “Nothing seems to work the first few times/Am I right?”

217. “Hold On,” With Jack Ingram (2008)

An early country throwaway, released a decade later on Ingram’s From the Vault: Live 2007-2009. A teenage Swift chirps back-up harmony, doing the part originally sung by Sheryl Crow.

Best line: “Sign our names in the dust on your family car.”

216. “Beautiful Ghosts” (2019)

She wrote this with Andrew Lloyd Webber for the Cats soundtrack — as she said, “If you can’t get T.S. Eliot, get T.S.”

Best line: “I watch from the dark, wait for my life to start / With no beauty in my memory.”

215. “Girl at Home” (2012)

A perfunctory cheating-is-bad homily, with barely any chorus.

Best line: “I feel a responsibility/To do what’s upstanding and right.”

214. “Half of My Heart,” With John Mayer (2009)

The real prize from his Battle Studies album is “Heartbreak Warfare”; this is lesser J.M., with an underexploited T.S. cameo and an increasingly irritating premise of hearts having fingers, which they don’t. No wonder the girl in the dress cried the whole way home.

Best line: “Half of my heart’s got a grip on the situation.”

213. “Sweeter Than Fiction” (2013)

A warm-up for the synth-pop of 1989, from the One Chance soundtrack.

Best line: “What a sight when the light came on.”

212. “Superman” (2010)

https://youtu.be/yWta_6F1ejQ

A Lois Lane fantasy, left off Speak Now for good reason.

Best line: “Tall, dark and beautiful/He’s complicated, he’s irrational.”

211. “Cold as You” (2006)

“I start a fight ’cause I need to feel something” – give her credit for honesty, even in this raw phase.

Best line: “Every smile you fake is so condescending.”

210. “If This Was a Movie” (2010)

https://youtu.be/Bqj9EIgSy28

“Good evening, sir. May I help you? You’re a guy in a Taylor Swift song who wants to stand outside the window in the pouring rain, begging the love of your life to forgive your sorry ass? Take a number and get in line. No, that line.”

Best line: “But I take it all back now!”

209. “A Perfectly Good Heart” (2006)

“It’s not unbroken anymore”? Paging the eminent cardiologist Dr. Toni Braxton.

Best line: “Why would you wanna make the very first scar?/Why would you wanna break a perfectly good heart?”

208. “White Christmas” (2007)

Unlike “Silent Night,” this was a yuletide carol she could handle, with a straight-down-the-middle country rendition.

Best line: “Where the treetops glisten.”

207. “I Don’t Wanna Live Forever,” With Zayn Malik (2016)

Neither she nor Zayn sound deeply interested in this dueling-falsettos battle from the Fifty Shades Darker soundtrack. Maybe it works in the movie, but who wants to go find out? Really, they sound like two ghosts standing in the place of…sorry, sore subject, let’s drop it.

Best line: “I’ve been looking sad in all the nicest places.”

206. “Mary’s Song (Oh My My)” (2006)

A through-the-years romance, with a sweet homespun touch.

Best line: “I’ll be 87, you’ll be 89/I’ll still look at you like the stars that shine in the sky.”

205. “Highway Don’t Care,” With Tim McGraw and Keith Urban (2013)

A duet from McGraw’s album Two Lanes of Freedom, with a guitar solo from Keith Urban. The plot: His ex is driving away, listening to a Taylor song on the radio, as Tay tries to coax the woman into turning the car around and going home. Perhaps McGraw’s finest duet since his great lost Nelly jam, “Over and Over.”

Best line: “I bet you’re bending God’s ear talking ’bout me.”

204. “Change” (2008)

Oh, the fall of 2008 – Chuck and Blair were still an item, Suede was killing it on Project Runway, and “Change” was a de facto victory song for Obama, complete with a thumbs-up for the “revolution.” Yeah, those were different times.

Best line: “These walls that they put up to hold us back will fall down.”

203. “Nashville” (2011)

A cover of an obscurity by country singer David Mead, tucked away as a bonus on the Target edition of the Speak Now Tour Live DVD.

Best line: “Was that a blood or wine stain on your wedding dress?”

202. “Sweet Escape” (2011)

From the same live DVD, a remake of the Gwen Stefani solo hit. Taylor’s vocal sure fits the Gwen just-a-girl sensibility.

Best line: “I must apologize for acting stank.”

201. “Only the Young” (2019)

“Only the Young” debuted in her excellent doc Miss Americana, a synth-pop tribute to the next generation of political activists. It’s also a clever Swiftian fake-out, giving everyone a totally wrong idea of where she was headed musically — almost like she was announcing, “Nothing to see here, folks. Definitely no keepers left over from the Lover era.” Was she already plotting to catch us off guard with Folklore? Don’t put it past her. But you’d never guess she was about to make an acoustic album full of folk songs about sweaters.

Best line: “Up there’s the finish line / Our future is worth the fight.”

200. “I’d Lie” (2006)

A perky early throwaway about a teenage crush, recorded for her debut and briefly released as a bonus track.

Best line: “He loves to argue, born on the 17th.”

199. “Umbrella” (2008)

The Rihanna hit, briefly covered on the Live from SoHo digital album. Her finest Ri tribute remains her 2011 version of “Live Your Life” with T.I. onstage in Atlanta – sadly unreleased, but a duet that deserves to be enshrined for the ages.

Best line: “Stand under my umbrella, ella, ella.”

198. “Look What You Made Me Do” (2017)

The reason fans once cared about rap beefs: they inspired great songs, whether it was Queens vs. the Bronx (“The Bridge” vs. “The Bridge Is Over” vs. “Have a Nice Day”) or LL Cool J vs. Kool Moe Dee (“How Ya Like Me Now” vs. “Jack the Ripper” vs. “Let’s Go” vs. “To Da Break of Dawn”). But this just sounds like a trivial time-waster by her standards – Swift’s celebrity feuds are not really one of the hundred most interesting things about her. The main attraction is the retro Panic! at the Disco vibe. “Look What You Made Me Do” turned out to be the lamest track on Reputation, but an impressively perverse head fake – a lead single that ended up having nothing to do with the album, musically or conceptually, making sure her new relationship songs would come as a surprise. To find a comparable stunt, you might have to go back to 1982, when Michael Jackson fooled the world into thinking Thriller was going to be a whole album of “The Girl Is Mine.”

Best line: “It’s much better to face these kinds of things with a sense of poise and rationality.” Oh wait – that actually is Panic! at the Disco.

197. “Never Grow Up” (2010)

A folksy fingerpicking change of pace on Speak Now, pining for childhood innocence – though it feels more like a leftover from the debut.

Best line: “You’re mortified your mom’s dropping you off.”

196. “Stay Beautiful” (2006)

An early stab at a take-the-high-road breakup song.

Best line: “He whispers songs into my window.”

195. “I Want You Back” (2010)

A live acoustic tribute to the then-recently departed Michael Jackson, with a bit of Motown tremble in her voice.

Best line: “Oh darling, I was blind to let you go.”

194. “End Game” (ft. Ed Sheeran & Future) (2017)

Future reaffirms her long-running bond with ATLien hip-hop, which goes back to her B.o.B. and T.I. duets. Plus her trusty wingman Ed Sheeran. She offers an update about her lipstick status (still red! good to know) and her relationship with drama: “I swear I don’t love the drama — it loves me!”

Best line: “I bury hatchets, but I keep maps of where I put ‘em.”

193. “September” (2018)

The Earth, Wind & Fire classic, already covered by every wedding band on the planet, becomes a mournful banjo lament. It’s her tribute to the late great Maurice White, a songwriter who shared her knack for building hits out of quirky details. (Changing “the 21st night of September” to the 28th is a very Swiftian touch.) Next she might try “That’s the Way of the World” or “After the Love Has Gone.”

Best line: “Love was changing the minds of pretenders.”

192. “That’s When” (2021)

A Fearless outtake refurbished as a duet with her old friend Keith Urban. She pleads for forgiveness after crushing a lover’s heart for no particular reason, in the mode of “Back to December” or “Afterglow.”

Best line: “I knew my words were hard to hear/And harder to ever take back.”

191. “The Way I Loved You” (2008)

She meets a low-stress boy who doesn’t want love to be torture. Alas, this suitor is toast, because he reminds her how much she misses the manic pixie drama vampire she dated before. Sorry, dude – she loves the players, and she loves the game.

Best line: “He respects my space/And never makes me wait.”

190. “Thug Story,” With T-Pain (2009)

The classic T-Pain and Taylor duet from the 2009 CMT Awards, still T-Swizzle’s finest rap performance.

Best line: “No, I never really been in a club/Still live with my parents, but I’m still a thug/I’m so gangsta you can find me baking cookies at night/You out clubbing, but I just made caramel delight.”

189. “I Wish You Would” (2014)

One of her many, many songs set at 2 a.m. – clearly the most inspiring hour on Swift Standard Time – with a staccato disco guitar lick.

Best line: “We’re a crooked love in a straight line down.”

188. “Big Star,” With Kenny Chesney (2017)

“This song is about a girl who had a dream and followed it,” Kenny Chesney tells the roaring Nashville crowd. One of those girls jumps onstage to sing along. “My friend Taylor Swift showed up on my birthday to surprise me,” Kenny explained. “In a lot of ways, that song and that lyric is Taylor’s journey.” Their touching “Big Star” duet came out on his concert album Live from No Shoes Nation — 10 years after he gave this rookie a break as the opening act on his 2007 summer tour. There is no loyalty like Swift loyalty.

Best line: “She signed autographs like she was Garth Brooks in a skirt.”

187. “I Forgot That You Existed” (2019)

Subtitle: “So I Sang About You First Thing On My Album.” So yeah, maybe that’s the opposite of forgetting — it’s technically known as “reminding.” Letting go of the past, moving on, calming down — let’s face it, those aren’t exactly topics where you look to Taylor for guidance. That’s why we love her — she never lets go. (She hasn’t forgotten Drew!) But there’s something quintessentially Tay about how she keeps nudging to impress you with how indifferent she is. Her Aubrey Graham shout-out is fitting, since these two are the champion overfeelers of our time.

Best line: “In my feelings more than Drake.”

186. “I Heart ?” (2008)

The trad country sound she soon left behind, from her Beautiful Eyes EP.

Best line: “Wake up, and smell the breakup/Fix my heart, put on my makeup.”

185. “Gasoline (Remix),” With Haim (2020)

Taylor officially joins the family as the fourth Haim sister. This anger-and-lust guitar jam was a highlight of their excellent Women In Music, but it gets even better with Sister Swift singing along. It’s funny they didn’t have her do the line “Watching the sun rise from the kitchen counter,” since she’s the one who’s on a mission to have emotional experiences in every square inch of the kitchen.

Best line: “You needed ass/Well, what’s wrong with that?”

184. “Breathe” (Ft. Colbie Caillat) (2008)

A gorgeous duet full of low-key nuances – her humming after the first verse, that “sorry, sorry, sorry” fade, the way Colbie’s voice lifts hers.

Best line: “It’s tragedy, and it’ll only bring you down.”

183. “Untouchable” (2009)

A rare case where she retools somebody else’s song on one of her proper albums – the all-but-unknown Y2K-era rock band Luna Halo, who previously opened for Hoobastank. Her Fearless version sounds practically nothing like their original (though both name-check .38 Special’s Eighties classic “Caught Up in You“). In fact, it’s tough to fathom how she heard the original as raw material she could use – now that’s ears.

Best line: “In the middle of the night when I’m in this dream/It’s like a million little stars spelling out your name.”

182. ‘The Joker and the Queen,’ with Ed Sheeran (2022)

An Ed Sheeran ballad, refurbished into a sweet duet with his long-running favorite co-star. The video has the same actors who played Ed and Tay as little kids in the “Everything Has Changed” video—ten years later. Both singers sound right at home with the metaphor of a poker game—Ed can’t see it in her face, but she’s about to play her ace. 

Best line: “I’ve been played before, if you hadn’t guessed / So I kept my cards close to my foolproof vest.”

181. “Pour Some Sugar On Me,” With Def Leppard (2008)

She makes a daring leap into the hair-metal mom market by teaming up with Def Leppard on CMT Crossroads, a move that works almost frighteningly well. Peak glam, especially when she asks the gender-torching question, “Demolition woman, can I be your man?”

Best line: “Do you take sugar? One lump or two?”

180. “Christmases When You Were Mine” (2007)

Taylor writes her own ace lovelorn holiday standard, ambushing her ex with one of those squirm-packed Merry-Christmas phone calls. Awkward question: “When you were putting up the lights this year/Did you notice one less pair of hands?” Eat your heart out, Mariah.

Best line: “I bet you got your mom another sweater.”

179. “American Girl” (2009)

A bang-up claim on the Tom Petty classic – she used his original as her live entrance music for a while. Then she switched to Lenny Kravitz’s “American Woman.”

Best line: “Oh yeah! All right!”

178. “Invisible” (2006)

https://youtu.be/jtG113v09xg

A teen ditty about a boy who doesn’t realize she’s alive, from pretty much the last moment in history that was possible. Clever pop-obsessive touch: The final steel-guitar twang echoes Elton John’s “Rocket Man.” If you think that’s an accident…this is Planet Tay. There are no accidents.

Best line: “We could be a beautiful miracle, unbelievable, instead of just invisible.”

177. “Jump Then Fall” (2009)

Ironclad rule of pop music: Songs about jumping are never a bad idea. Dig that “listens to Sublime once” vocal.

Best line: “I watch you talk, you didn’t
notice.”

176. “Breathless” (2010)

Digging deep in the Nineties modern-rock crates, she does right by a previously obscure (to me) nugget from the New Orleans band Better Than Ezra – from 2005!, 10 years after their MTV hit! – as a charity benefit for the Hope for Haiti Now album.

Best line: “I’ll never judge you/I can only love you.”

175. “Better Than Revenge” (2010)

One of the basic rules of stardom is “never punch down” – don’t go after somebody one-thousandth as famous as you – but rules were made to be broken, and Taylor is the girl made to break them. Here, she goes Bruce Lee on a sexual rival who may or may not be the actress who had Alyssa Milano as her babysitter in the erotic thriller Poison Ivy 2. But as usual with Swift, her self-owns are the funniest part of the song.

Best line: “She thinks I’m psycho because I like to rhyme her name with things.”

174. “Gorgeous” (2017)

Swift hits the club with her older boyfriend and gets her pheromones scrambled by the sweet young thing across the room. Dig those Eighties synth tones — straight from the first Howard Jones album. Tragic fact: Seven years after she wrote “Enchanted,” Taylor still has zero “find out if dude has a freaking girlfriend” game. The shout-out to her cats Meredith and Olivia is such a cheap ploy, and you know what? It works brilliantly, as cheap ploys usually do when this is the woman working them. This song could rate higher, except she basically did an even better version with “You Need to Calm Down.”

Best line: “You should take it as a compliment that I’m talking to everybody here but you.” Listen here.

173. “Paris” (2022)

“I wanna brainwash you into loving me forever / I wanna transport you to somewhere the culture’s clever”—for Tay, that means a fantasy of Gay Paree. But the whole point of this song is that you can make your own Paris wherever you are, just by drawing your own dream map on the bedroom ceiling. And if you have an amour to share the dream with, all the better. “All the outfits were terrible, 2003 unbearable”—sounds like Taylor found somebody’s Friendster photo stash of crop tops and trucker hats. “Did you see the photos? / No, I didn’t, but thanks though” is being kind. 

Best line: “Privacy sign on the door and on my page and on the whole world / Romance is not dead if you keep it just yours.”

172. “Birch,” With Big Red Machine (2021)

A Big Red Machine ballad sung by Bon Iver’s Justin Vernon, with Taylor in a supporting role. She adds her celestial harmonies, picking up where the Justin/Taylor duets “Exile” and “Evermore” left off. Aaron Dessner summed up the spirit of the project: “Making music with your friends just to make it.”

Best line: “So I beg on knees/Can we share IDs?”

171. “Gold Rush” (2020)

“My mind turns your life into folklore” is a clever way to connect Evermore to Folklore, although “Gold Rush” might have sounded more at home on Lover. “Gold Rush” could be a different view of the same torpor as “Happiness” and “Tolerate It,” trying to remember why this relationship once seemed worth the pain.

Best line: “My Eagles t-shirt hanging from the door.”

170. “Christmas Tree Farm” (2019)

Once upon a time, many Christmases ago, the label made poor Taylor bang out a shoddy quickie holiday album in time for December. She must have wondered, “Why is this happening? Why am I singing ‘Santa Baby’? WTF, shouldn’t I be singing about how in real life I literally grew up on a Christmas tree farm?” It took a few years, but she finally got to jingle all the way, with this impeccably cozy carol.

Best line: “Sweet dreams of holly and ribbon / Mistakes are forgiven.”

169. “Superstar” (2009)

“You smile that beautiful smile, and all the girls in the front row scream your name.” No relation to the Seventies soft-rock hit by the Carpenters — except they’re both poignant ballads about groupies crushing on distant guitar boys. Well, as Journey warned, lovin’ a music man ain’t always what it’s supposed to be.

Best line: “You sing me to sleep every night from the radio.”

168. “False God” (2019)

Her wintry tribute to Eighties R&B — that sax sounds like it dropped in from a lost Sade album between Promise and Love Deluxe. The highlight of “False God” is the final 30 seconds, where she sings exactly like Drake. She’s showing off, but it’s all right.

Best line: “Staring out the window like I’m not your favorite town / I’m New York City.”

167. “Crazier” (2009)

Her ballad from Hannah Montana: The Movie, snagging her a cameo in the film. (But the highlight of the soundtrack will always be “Hoedown Throwdown.”) This is where Taylor and Miley crossed light sabers – although they’d meet again. Great title, too – even Taylor might probably admit Miley had her beat in this department, at least until the “Blank Space” video.

Best line: “Every sky was your own kind of blue.”

166. “Innocent” (2010)

Little-known fact: Did you know Kanye West once went onstage to interrupt Swift’s acceptance speech at the VMAs and threw a misogynist tantrum about how she didn’t deserve an award? Strange but true! “Innocent” was her song publicly forgiving him — over 10 freaking years ago — then they both released brilliant albums and we all moved on with our lives. Dear Lord, if only this story had ended there.

Best line: “It’s OK/Life is a tough crowd.”

165. “…Ready for It?” (2017)

Baby, let the games begin. Her island-breeze bass blast was a major rebound from her previous hit, one week earlier. (If by “it” she meant “literally any song that’s not ‘Look What You Made Me Do,’” the answer was “extremely ready.”) It stands up to heavy rotation, too, with clever details like the way Ms. I’m Not Much For Dancin’ clears her throat before the first line. The chorus has a little air in the mix, giving the room she needs to pull off her intricate breathy effects; Max Martin really knows how to shape a production around her voice. “He can be my jailor / Burton to this Taylor” – Liz and Dick got married and divorced twice, so those are some hardcore relationship goals.

Best line: “I keep him forever like a vendetta.”

164. “Midnight Rain” (2022)

One of Taylor’s favorite heroines to write about: the small-town girl who broke free and ran off to the big old city because she wanted to chase the fame, only to wonder if she blew her shot at everyday happiness with the boy next door. (She probably didn’t.) “Midnight Rain” does the Prince trick of a butch/femme duet with her own electronically warped voice, enhancing the mood of nocturnal regret. The road not taken looks real good now.

Best line: “My boy was a montage.”

163. “Tied Together With a Smile” (2006)

An unsung highlight of the debut – a teen pep talk about self-esteem.

Best line: “Seems the only one who doesn’t see your beauty/Is the face in the mirror looking back at you.”

162. “Don’t You” (2021)

A synth ballad rescued from the Fearless vault, where Taylor bumps into an ex-boyfriend and decides whether she feels like taking the high road or making a scene. Shocker: she makes a scene.

Best line: “Hey, I knew I’d run into you somewhere/It’s been a while, I didn’t mean to stare.”

161. “This Is Why We Can’t Have Nice Things” (2017)

The most “therein” moment on Reputation. Also the only song (after “Look What You Made Me Do”) devoted to the album’s alleged celebrity-complaints concept, though shrewdly playing it for kicks and giggles. “Therein lies the issue” is some quality Swiftian spite content, but it’s that sadistic tongue-clicking “mmm-mmmm” before the second chorus that really brings the Judgement Tay. “Here’s to my mama, had to listen to all this drama” – has your mom met you? She might be used to that by now.

Best line: “Feeling so Gatsby for that whole year.”

160. “Stay Stay Stay” (2012)

“Before you, I’d only dated self-indulgent takers” – but here she turns into a self-indulgent taker herself and (surprise!) she likes it, a phone-throwing nightmare dressed like a grocery-shopping daydream. But she’s more in love with more mood swings than she is with the guy.

Best line: “You came in wearing a football helmet and said, ‘Okay, let’s talk.’”

159. “Message In a Bottle” (2021)

The first song Swift wrote with Max Martin and Shellback — the day she met them. It makes sense she left “Message in a Bottle” off Red, since it sounds so similar to “22”— she chose the right one. But it sounds like she’s already stretching ahead to 1989. “How is it in London?” sounds like a fresh take on the transatlantic rendezvous of “Come Back…Be Here.”

Best line: “I became hypnotized by freckles and bright eyes, tongue-tied.”

158. “Closure” (2020)

Nothing could be more contrary to the Taylor worldview than the concept of “closure.” Needless to say, she’s opposed to it.

Best line: “Don’t treat me like some situation that needs to be handled/I’m fine with my spite and my tears and my beers and my candles.”

157. “Come In With the Rain” (2008)

She leaves her window open overnight, just in case her ex falls out of a cloud. There’s a great “oooh” in the second chorus — one of those moments you can tell she’s an Oasis fan. (This song makes you suspect “Don’t Look Back In Anger” is a fave.) One of the Fearless-era tunes that gets a drastic glow-up on Taylor’s Version — it sounds infinitely better when she gets to belt it in her adult voice.

Best line: “I could stand up and sing you a song/But I don’t wanna have to go that far.”

156. “Last Christmas” (2007)

Tay does the Wham! legacy proud – she should also cover “Wake Me Up Before You Go-Go.” The ache and quaver of her voice fit the George Michael melancholy; this might be the saddest “Last Christmas” since the original. Plenty of us communed with this version on Christmas 2016, the night we said goodbye to the guy who wrote it. R.I.P., George Michael.

Best line: “A girl on a cover but you tore her apart.”

155. “Long Story Short” (2020)

Taylor has never once in her life made a long story short, and who would want her to? This synth-pop bop adds a dash of Reputation energy to the stark autumnal vibe of Evermore. I love how if she could go back in time, she’d tell her younger self all the things she actually did say a decade ago. “Your nemeses will defeat themselves before you get the chance to swing” is basically the same sentiment as “people throw rocks at things that shine.”

Best line: “If the shoe fits, walk in it till your high heels break.”

154. “Tell Me Why” (2008)

From Neil Young to the Beatles, “Tell Me Why” songs are tough to screw up, and even at 19, Tay’s too seasoned to let that happen.

Best line: “I need you like a heartbeat/But you know you got a mean streak.”

153. “Epiphany” (2020)

Inspired by her grandfather, a World War 2 veteran who landed on Guadalcanal in 1942. “Holding hands through plastic” is a stark image of the Covid-19 pandemic.

Best line: “Something med school did not cover / Someone’s daughter, someone’s mother.”

152. “All You Had to Do Was Stay” (2014)

A 1989 banger that could have made an excellent single – it sounds a bit like “Out of the Woods,” except with a livelier chorus and a stormier range of electro-Tay sound effects.

Best line: “Let me remind you this was what you wanted.”

151. “Karma” (2022)

“Karma is my boyfriend” is a great hook from this surprisingly perky chorus. A Midnights track that feels like a leftover from the past, especially since she already wrote a reply to this one two years ago, with “Long Story Short,” advising “past me” to let go of petty distractions and just let her nemeses defeat themselves. 

Best line: “Karma is a cat.”

150. “Paper Rings” (2019)

“The moon was high like your friends were the night that we first met” is quite an opening line, and she lives up to it. Especially since those might be the same stupid friends who showed up later at Betty’s party. “Paper Rings” is a girl-group tribute with a pop-punk surge — a song Joey Ramone should have lived long enough to sing. “I wake up in the night and watch you breathe” is a bone tossed to all of us who still fall apart at the bridge of “Last Kiss.”

Best line: “I hate accidents, except when we went from friends to this.”

149. “You All Over Me,” With Maren Morris (2021)

The first outtake she let slip from the Fearless vault was a proof-of-concept coup. Still just 17, she writes a song about getting clean, but decides to keep it a secret, so she can wait six years to release her classic “Clean,” then wait six *more* years to release this prequel. I do not understand how this mind exists — honestly, it’s just scary.

Best line: “Your hands in your pockets/And your ‘don’t you wish you had me’ grin.”

148. “I Think He Knows” (2019)

Lusty finger-snaps, crushed-out heavy breathing, skipping down 16th Avenue. (Isn’t that underwater in the Hudson River?) “It’s like I’m 17 / Nobody understands” is hilarious considering that when she was 17, she had the world wired to every teardrop on her guitar.

Best line: “He’s so obsessed with me, and boy, I understand.”

147. “Beautiful Eyes” (2008)

If you’re a fan of Swift’s Nineties modern-rock radio jones – one of her most fruitful long-running obsessions – check out this shameless tribute to the Cranberries. (But did she have to let it linger? Did she have to? Did she have to?)

Best line: “Baby, make me fly.”

146. “Dancing With Our Hands Tied” (2017)

“Dancing With Our Hands Tied” has more of Romeo and Juliet‘s actual plot than “Love Story” did. She slips away in secret with a forbidden lover who paints her blue heart gold, over Eighties “Take On Me”-style beats. The saddest line Fiona Apple ever wrote – “I know I’m a mess he don’t wanna clean up” – finally finds a new home in a Swift song: “I’m a mess, but I’m the mess that you wanted.”

Best line: “I’d kiss you as the lights went out / Swaying as the room burned down.”

145. “You Need to Calm Down” (2019)

The first time I heard “Welcome to New York,” back in 2014, I thought people would freak out over the explicit pro-queer lyrics. (“Boys and boys and girls and girls” — she was not afraid to burn her bridges.) But of course, people slept on it. So I love how she just did it a little louder for the people in back. Eighties New Wave synth-pop was one of the gayest musical movements ever, but at the time, it was all hidden — virtually none of the genre’s (many) queer artists were out. So it’s fitting how her New Wave homage foregrounds the music’s LGBTQ roots. When she growls, “Damn, it’s 7 a.m.” we all know Taylor has been up pacing the floor at 2 a.m., because that’s what she does.

Best line: “Can you just not step on our gowns?”

144. “Dear Reader” (2022)

“Reader, I married him” is one of the most famous lines in 19th century novels, from Charlotte Bronte’s Jane Eyre, so “Dear Reader” is a suitable flex for Quill Pen Taylor, stretching her lit muscles after “The Lakes.” It evokes the end of the “All Too Well” short film, when Author Taylor appears at the bookstore, with a crowd full of readers under her spell. It’s a clever irony for her to warn, “Never take advice from someone who’s falling apart”—especially since the art of falling apart is her favorite topic for giving advice.

Best line: “Dear reader, the greatest of your luxuries is your secrets.”

143. “No Body, No Crime,” With Haim (2020)

A country collabo with her longtime friends in Haim, for a “Goodbye Earl”-style murder story with a shout-out to Olive Garden. Clever detail: the killer husband reveals his guilt by buying “brand new tires,” continuing Taylor’s recent fascination with shiny wheels. Question: Why did he buy new tires right after committing a murder? Is he the only guy who’s never seen Goodfellas? It’s like Robert De Niro says: “Don’t buy anything!” What a Johnny Roastbeef mistake.

Best line: “She was with me, dude.”

142. “Drops of Jupiter” (2011)

I mistakenly thought this Train hit was deep-fried garbage until I heard Swift’s version and realized, “Hey, she’s right – this is the best soy latte I’ve ever had!” Props to Tay for bringing out the hidden greatness in this song – the stargazing lyrics and her voice go together like Mozart and tae bo. (The astrophysicist in my life would like me to point out that you can’t “make it to the Milky Way” because that’s the galaxy we already live in. In fact, you couldn’t leave the Milky Way if you tried. Science!)

Best line: “Tell me, did Venus blow your mind?”

141. “King of My Heart” (2017)

Love how this American queen pronounces “Jag-yew-waaar” – has she been listening to Hall & Oates, or has she just reached the English-accent point in her fame arc?

Best line: “Up on the roof with a schoolgirl crush / Drinking beer out of plastic cups.”

140. “The Very First Night” (2021)

An easy Red vault track to overlook, but the dance-pop zoom of “The Very First Night” could have fit right on 1989. It makes a worthy part of the trilogy with “Come Back…Be Here” and “Message in a Bottle.” She’s causing trouble up in hotel rooms with a jet-set rock-star boyfriend — a predicament she’d explore in detail more later.

Best line: “Don’t forget about the night in L.A./Dance in the kitchen, chase me down the hallway.”

139. “Glitch” (2022)

An understated electro-ballad produced with Sounwave, giving thanks for some benevolent fluke of the universe (did some bird flap its wings over in Asia?) that has resulted in a functional romantic situationship. “2,910 days of our love blackout”—that’s six years, or approximately how long Swift has been with Joe Alwyn. And she released it on the 12,000th day of her life? Hardcore. Lifted high by Midnights’ loveliest back-up vocals.

Best line: “I was supposed to sweat you out, in search of glorious happenings of happenstance on someone else’s playground.”

138. “Haunted” (2010)

Enchanted to meet you, Goth Taylor. We’ll meet again.

Best line: “Something keeps me holding on to nothing.”

137. “Today Was a Fairytale” (2011)

Don’t let the title scare you away – it’s a plainspoken and genuinely touching play-by-play recap of a worthwhile date. In fact, “Today Was a Fairytale” and “If This Was a Movie” should trade titles, since this one feels realer and would make a better movie. It could rank higher, except she hugely improved it when she rewrote it as “Begin Again.” (Docked a couple notches for coming from the soundtrack of Valentine’s Day, which is the most dog-vomit flick Jessica Alba has ever made, and I say that as someone who paid money to see The Love Guru.)

Best line: “I wore a dress/You wore a dark gray T-shirt.”

136. “The Other Side of the Door” (2008)

Again with the slamming doors. Tay, Tay — even the great songwriters can get away with exactly one slamming door per career. And just to be on the safe side, she throws in pouring rain, photo albums, a little black dress (which rhymes with “mess” and “confess”), a guy throwing pebbles at her window… In other words, this would be the ultimate Swift song — except there are over a hundred better ones. But “The Other Side of the Door” gets a boost from the Taylor’s Version remake — of all the Fearless tunes, this one improves most drastically on the original. Her mature voice tackles the melody in ways her teen voice couldn’t, sprucing up a dud into a keeper. This is the biggest sonic upgrade in the Taylor’s Version project. So far.

Best line: “Me and my stupid pride, sitting here alone/Going through the photographs, staring at the phone.”

135. “Can’t Stop Loving You” (2019)

When Taylor stopped into the BBC’s Live Lounge, she had a surprise up her sleeve: This Eighties pop aficionado busted out a Phil Collins cover, against all odds. “Can’t Stop Loving You” is a 1970s obscurity that Phil turned into a sleeper hit in 2002. As Taylor explained, “I remember driving around Nashville when I first had my driver’s license just screaming the words to this song.” It’s perfect for her — for one thing, it’s about crying in the back of a taxi. If Taylor wants to keep digging into the Phil catalog, maybe she’ll cover “I Don’t Care Anymore.”

Best line: “Got your leaving smile.”

134. “Speak Now” (2010)

In real-life weddings, the preacher hardly ever invites the groom’s ex up to interrupt the ceremony. But if you’re a fan of Tay in stalker mode, this is priceless – crouching behind the curtains in the back of the church, waiting to pounce. “Horrified looks from everyone in the room” – you don’t say.

Best line: “It seems I was uninvited by your lovely bride-to-be.”

133. “It’s Time to Go” (2021)

Taylor sings about a bad situation where she realizes when it’s time to give up and move on — not exactly her specialty. There’s different types of betrayal going on in this song, but the big moment is when she vows, “He’s got my past behind frozen glass, but I’ve got me.” (It’s like Hall & Oates sang: “The strong give up and move on, while the weak give up and stay.” Tay has so much in common with Hall & Oates.)

Best line: “Fifteen years, fifteen million tears, begging till my knees bled.”

132. “Run,” With Ed Sheeran (2021)

This Ed Sheeran duet from the Red vault is about two outlaw lovers making an upstate escape in the car — it makes a clever contrast with the drive in “All Too Well (10-Minute Version),” with Taylor at the wheel. This song also has the album’s second-most-memorable cameo from a keychain. Not as dramatic as “Everything Has Changed,” but every bit as intimate. (And if I’m not mistaken, it’s about something good that starts in a getaway car.)

Best line: “I could see this view a hundred times/Pale blue sky reflected in your eyes.”

131. “Lavender Haze” (2022)

A Nineties R&B trip through the “Lavender Haze,” with two lovers in their own private world, tuning out society and gender roles and social media, blocking out the noise, leaving it all at their door. It’s a kind of love story she’s kept singing about her whole career, from “Ours” to “Holy Ground” to “Call It What You Want.” Taylor rejects “the 1950s shit they want from me,” where “the only kind of girl they see is a one-night or a wife.” Intriguing footnote: At her NYC commencement speech in May, Dr. Swift revealed, “I had a phase where, for the entirety of 2012, I dressed like a 1950s housewife.”

Best line: “Staring at the ceiling with you / You don’t ever say too much / And you don’t really read into my melancholia.”

130. “The 1” (2020)

The one Folklore track that sounds like a continuation of Lover, with its languid finger-snapping Motown slink. “Roaring Twenties, tossing pennies in the pool” — Taylor’s long-term relationship with The Great Gatsby just keeps on giving. She closes the book on her twenties, while kissing off this “not exactly roaring at the moment” decade.

Best line: “In my defense I have none, for digging up the grave another time.”

129. “Afterglow” (2019)

An ode to making up after a fight that was all your fault: “Tell me that I’m all you want / Even when I break your heart.” In a good old-fashioned Taylor metaphor party, she compares herself to an arsonist, a wrestler, an island, a prison warden and an ambulance siren.

Best line: “Fighting with a true love is boxing with no gloves.”

128. “You Belong With Me” (2008)

One of her most pop-friendly early hits, singing in the role of a high school geek crushing on her best guy friend. When he comes out in college, they’ll have a few laughs about this. And never let us forget the wisdom of Alicia Silverstone in Clueless: “Searching for a boy in high school is as useless as searching for meaning in a Pauly Shore movie.”

Best line: “She wears high heels, I wear sneakers/She’s cheer captain, and I’m on the bleachers.”

127. “So It Goes…” (2017)

She falls under the hypnotic spell of a magician, who gets her heart trip-trip-tripping and skip-skip-skipping. For a magic trick of her own, she stops the music cold to whisper “one-two-three.” A great moment that lets you know Swift — like the rest of us — has been listening to Lorde.

Best line: “I’m so chill but you make me jealous.”

126. “You’re Not Sorry” (2008)

A dramatic piano-and-strings ballad from Fearless, showing off how much her voice has deepened between her first two albums.

Best line: “It’s taken me this long, baby, but I figured you out.”

125. “Bette Davis Eyes” (2010)

Her kickiest left-field cover, from Speak Now Live. “I’d love to play you some music that I’m a fan of that’s come from L.A. – is that OK?” she asks the West Coast crowd, strumming her guitar. “This one came out in 1981 – eight years before I was born!” Virtually nobody seems to recognize it or sing along. Kim Carnes hit Number One with “Bette Davis Eyes,” but it was written by the great Jackie DeShannon, the only songwriter to collaborate with both Randy Newman and Jimmy Page. (Page wrote “Tangerine” for DeShannon!) The fact that Swift loves this classic ode to romantic espionage explains a lot.

Best line: “She’s pure as New York snow/She’s got Bette Davis eyes.”

124. “The Lucky One” (2012)

She’s so lucky, she’s a star. For the record, T.S. did cover “Lucky” live once (and damn well, too), as a Britney tribute in Louisiana back in 2011. This song got the ultimate real-life twist years later: the Red (Taylor’s Version) remake came out the same day Britney finally got free.

Best line: “Everybody loves pretty, everybody loves cool/So overnight you look like a Sixties queen.

123. “Question…?“

A very Taylor dilemma: “Does it feel like everything’s just like second-best after that meteor strike?” She gives a hint about this meteor by opening the song with a sample from “Out of the Woods.” Taylor cross-examines an ex with a slew of questions, although she wishes she didn’t already know the answers. There’s a great flashback to “Betty” in the chorus, when two lovers kiss in a crowded room, in front of all their stupid friends.

Best line: “It was one drink after another / Fucking politics and gender roles.”

122. “Shake It Off” (2014)

A clever transitional single – great verses, grating chorus, pithy lyrics with a shout-out to her obvious inspiration, Robyn’s “Dancing on My Own.” As a lead single, “Shake It Off” might have seemed meager after 1989 came out – she was holding back “Blank Space” and “Style” and (Lord have mercy) “New Romantics” for this? But “Shake It Off” got the job done, serving as a trailer to announce her daring Eighties synth-pop makeover.

Best line: “It’s like I got this music in my mind, saying it’s gonna be all right.”

121. “Everything Has Changed,” With Ed Sheeran (2012)

She and Ed Sheeran wrote this duet together in her backyard while bouncing on a trampoline, because of course they did. Why is Ed such a great duet partner? Because you can hear that he’s really listening to her.

Best line: “All I’ve seen since 18 hours ago is green eyes and freckles and your smile.”

120. “Peace” (2020)

The most stripped-down confession on Folklore, just her solo voice and a few guarded hopes for the future. She tries to scale her dreams down to a graspable size, asking, “Would it be enough if I could never give you peace?”

Best line: “Our coming-of-age has come and gone.

119. “Death By a Thousand Cuts” (2019)

The saddest break-up song ever inspired by a movie where Gina Rodriguez plays a Rolling Stone music critic, in Jenn Kaytin Robinson’s Oscar-worthy Netflix comedy, Someone Great. It really soars in the live acoustic version from her Paris concert special, especially the hyperventilating bridge. Good question: “If the story’s over, why am I still writing pages?” Taylor, have you met yourself?

Best line: “I asked the traffic lights if it’ll be all right / They say ‘I don’t know.’”

118. “Eyes Open” (2012)

Finally, her long-overdue metal move, from The Hunger Games: Songs from District 12 and Beyond.

Best line: “Every lesson forms a new scar.”

117. “Starlight” (2012)

“Oh my, what a marvelous tune” sounds like a quaint chorus, yet she makes it stick, in an F. Scott Fitzgerald-themed whirlwind romance. This Red deep cut just sat there waiting for its moment to shine, until it blew up into her de facto sequel “The Last Great American Dynasty,” with a nastier perspective on the same ritzy social scene. Nobody knows how to play the long game like Taylor.

Best line: “We snuck into a yacht-club party / Pretending to be a duchess and a prince.”

116. “Don’t Blame Me” (2017)

She tries on the moody “bad girl goes to church” vibe of Madonna circa Like a Prayer – addicted to love, falling from grace, going down on her knees to beg for one more kiss.

Best line: “My name is whatever you decide.”

115. “Forever & Always” (2008)

She added this to Fearless at the last minute – just what the album needed. It’s a blast of high-energy JoBro-baiting aggro on her most anomalously shade-free album. “It rains in your bedroom” is a very on-brand Tay predicament.

Best line: “Did I say something way too honest? Made you run and hide like a scared little boy?

114. “Bye Bye Baby” (2020)

One of the top-notch Fearless (Taylor’s Version) vault tracks. Like so many of her songs from this era, it has a giant Oasis-style hook: “You took me home, but you just couldn’t keep me.” Plus a bonus one in the bridge when she sings, “I’m so scaaared of how this ends!” What does it mean that the best Oasis songs of the past 20 years are Taylor songs?

Best line: “You’re all I want, but it’s not enough.”

113. “Soon You’ll Get Better,” With the Chicks (2019)

A touching duet with the Dixie Chicks (their final song under their old name) for her countriest tune in years, about her mother’s battle with cancer. It’s definitely heavy to hear the teenager who sang “The Best Day” and “Never Grow Up,” once so mortified her mom was dropping her off at the movies, now an adult driving her mom to the hospital.

Best line: “Holy orange bottles / Each night I pray to you.”

112. “High Infidelity” (2022)

A highlight of the Midnights 3 A.M. Edition. “High Infidelity” goes deep into the perils of musicians dating musicians, from “Put on your records and regret me” to “Put on your headphones and burn my city.” Taylor uses audio distortion as a metaphor for a bad romantic connection, a la Elvis Costello’s “High Fidelity,” though Midnights collaborator Zoë Kravitz also starred in the reboot of the classic High Fidelity. As for the question of what she was doing on April 29, 2016…listening to Lemonade and crying over Prince, like the rest of us? 

Best line: “There’s many different ways that you can kill the one you love / The slowest way is never loving them enough.”

111. “Back to December” (2010)

One of the rare ballads where she goes crawling back to an ex she treated like dirt – and she’s surprisingly effective in the role. Although breaking into the guy’s house is a little extreme. (If she’s blocked by the chain on his door, that means she already picked the lock, right?) And sorry, but you’re seriously dreaming if you think I’m bothering to Google the name of that Twilight guy, don’t @ me.

Best line: “It turns out freedom ain’t nothing but missing you.

110. “Tolerate It” (2020)

Can you even imagine the songwriter who wrote “White Horse” in her teens was already planning to write “Tolerate It” in her 30s? She might have taken inspiration from Rebecca, but it feels more like a Carole King song from the 1970s — trapped in a dead-end marriage where something inside just died. Taylor called this part of Evermore “the ‘unhappily ever after’ trilogy of marriages gone bad.”

Best line: “Now I’m begging for footnotes in the story of your life.

109. “I Almost Do” (2012)

We’re already at the zone on this list where every song seems like it should be ranked even higher, except it’s just so crowded at the top. For almost any other artist, “I Almost Do” would have been a career peak. A Red slow jam that could have worked even better sped up into a punked-out rocker — though it’s plenty affecting as is.

Best line: “Every time I don’t, I almost do.”

108. “Welcome to New York” (2014)

People sure do love to complain about this song – in fact, the most authentically New York thing about it is how it sends people into spasms of mouth-foaming outrage. An explicitly queer-positive disco ode to arrivistes stepping out in the city that invented disco – “You can want who you want, boys and boys and girls and girls” – that will be bugging the crap out of you in rom-coms for years to come. (It made me throw a napkin at my in-flight screen during How to Be Single, when Dakota Johnson’s cab is going the wrong way on the Brooklyn Bridge – and I love this song.) Bumped up a few bonus notches for pissing everyone off, since that’s one of this girl’s superpowers.

Best line: “Searching for a sound we haven’t heard before/And it said welcome to New York.”

107. “Wonderland” (2014)

Why did it take her five albums to get to Alice in Wonderland? Needless to say, Taylor Alison Swift fits right in on the other side of the looking glass, with white rabbits and Cheshire cats. Feed your head!

Best line: “It’s all fun and games till someone loses their mind.”

106. “We Were Happy” (2021)

This Fearless outtake would have made quite a highlight on the album. How did she let this one get away? Was it just too damn sad, even by *her* standards? To think of all the years we missed out on being traumatized by “You threw your arms around my neck/Back when I deserved it.” “We Were Happy” has both Liz Rose *and* Aaron Dessner in the credits, making this the perfect storm of Taylor weepers.

Best line: “Oh, I hate those voices telling me I’m not in love any more.”

105. “Mad Woman” (2020)

“They say ‘move on,’ but you know I won’t” — yes, we know. She’s always had a knack for songs about unrepentant old ladies, ever since her teens, and this “Mad Woman” could be Betty or Inez a few years down the line. But she could also be the heroine of “Dear John” or “15,” all grown up.

Best line: “Women like hunting witches too / Doing your dirtiest work for you / It’s obvious that wanting me dead has really brought you two together.

104. “London Boy” (2019)

Nice one, London! You have inspired a Taylor Travelogue even more over-the-top than “Welcome to New York,” with visits to Camden Market, SoHo, Highgate, and everyone’s favorite tourist destination, Hackney. As the English are so fond of saying, she over-eggs the pudding, and no wonder some skeptics got their knickers in a twist, but her Britpop tribute evokes the louche music-hall parodies of London bands from Madness to Blur. (She’s clearly been bumping Side One of Parklife.) The best part of this song is its wide-eyed enthusiasm, the least London of emotions. We need more of these, please — maybe she’ll do “Paris, Je T’Aime” or “Arigato Kyoto.”

Best line: “Stick with me, I’m your queen / Like a Tennessee Stella McCartney on the Heath.

103. “The Moment I Knew” (2012)

A somber piano ballad about getting stood up on your 21st birthday. This song got a major boost from the sequel “Happiness,” which Taylor happened to release exactly ten years after the party — just in time for her 31st birthday. But it stands out even more on Red (Taylor’s Version), as a companion piece to the expanded “All Too Well.” Has there ever been a more momentous birthday party in music history?

Best line: “There in the bathroom/I try not to fall apart.”

102. “Dorothea” (2020)

Could this be a hidden sequel to the Romantic poetry fetish of “The Lakes”? Dorothy was Wordsworth’s sister, muse and closest companion, just as Augusta was Lord Byron’s sister. “Dorothea” is the flip side to “’Tis the Damn Season,” sending a long-distance dedication to an old flame who moved on to a shinier life in Hollywood.

Best line: “The stars in your eyes shined brighter in Tupelo.”

101. “You Are in Love” (2014)

Another through-the-years romance, featuring a snowglobe. This 1989 outtake was underrated for years, until she cleverly interpolated it into the “Lover” video — where it all takes place inside the snowglobe.

Best line: “For once you let go of your fears and your ghosts.”

100. “Love Story” (2008)

Romeo meets Juliet: Proof that star-crossed teen romances never go out of style. But changing the plot of Romeo and Juliet so these two crazy kids end up together — now that’s some endearing Taylor hubris. She keeps going back to the well of Shakespearean tragedy, quoting Julius Caesar in the “Look What You Made Me Do” video. It’s never been clear what the line, “I was a scarlet letter,” is doing in this song, but now it’s a hint that Tay was just a few years away from going Full Hester Prynne in “New Romantics.”

Best line: “Just say yes.”

99. “Exile,” With Bon Iver (2020)

Back when Taylor broke up with that hipster dude in 2012, the one who was into “some indie record that’s much cooler than mine,” he was probably listening to Bon Iver. (“Beth/Rest,” damn.) She and Justin Vernon blend their very different voices, for the story of a Romeo and Juliet who never learned how to read each other’s minds. At first it sounded like their vocals just don’t fit together — yet that’s what the song is about. It really soars in the final minutes, as the piano and strings build.

Best line: “Like you’d get your knuckles bloody for me / Second, third, and hundredth chances / Balancing on breaking branches / Those eyes add insult to injury.”

98. “Out of the Woods” (2014)

When she finally gets around to 1989 (Taylor’s Version), this song stands to gain most. Jack Antonoff was just learning how to record her voice, and wow, he wasn’t even halfway there yet — it’s the production equivalent of a snowmobile wreck. Why did this song need male Tarzan yodels? It deserves a do-over, since the lyrics are packed with poignant details — did they take the Polaroid couch selfie before or after they moved the furniture so they could dance? The best version is live at the Grammy Museum in 2015 — no yodels, just Taylor emoting at her piano.

Best line: “Two paper airplanes flying, flying, flying.”

97. “Miss Americana and the Heartbreak Prince” (2019)

She wrote this Lana-esque tale as a political allegory — looking at the whole country as one big high school where the damsels are depressed, and the mean cheerleaders leer at bad, bad girls.

Best line: “The whole school is rolling fake dice / You play stupid games, you win stupid prizes.”

96. “I Know Places” (2014)

She goes all Kate Bush, pursued across the moors by the hounds of love. This 1989 deep cut is underrated, but count on “I Know Places” to loom large in her canon over the years.

Best line: “My love, they are the hunters, we are the foxes.”

95. “Hoax” (2020)

A desolate break-up lament, lifted by Aaron Dessner’s melancholy piano. Every Taylor album needs a tragic New York City romance, and “Hoax” revisits the holy ground where she’s loved and lost before — even on her least metropolitan album. “You know you won so what’s the point of keeping score?” is an apt question from such a compulsive emotional score-keeper.

Best line: “Don’t want no other shade of blue but you.”

94. “Picture to Burn” (2006)

The dawn of Petty AF Tay, as she serves her ex beatdown threats. Every boy who ever complained when Taylor wrote about him – this is where you officially got fair warning.

Best line: “Watch me strike a match on all my wasted time.”

93. “Carolina” (2022)

A Southern Gothic folk ballad in the Folklore/Evermore mode, from the movie Where the Crawdads Sing. It’s the story of a girl on her own in the North Carolina marshland, guarding secrets she’ll never share with anyone but the night. In many ways, “Carolina” feels like a sequel to “Cruel Summer,” but with bloodier secrets and a darker night. 

Best line: “Carolina pines, won’t you cover me? / Hide me like robes down the back road.” 

92. “The Best Day” (2008)

Her tribute to Mama Swift. A weapons-grade tearjerker and not to be trifled with in a public place. NSFW, unless you are a professional crier.

Best line: “You were on my side/Even when I was wrong.”

91. “The Story of Us” (2010)

You could credit this song with single-handedly driving John Mayer out of the pop heartthrob business and into the Grateful Dead – which is just one of the things to love about it. Along with the Joey Ramone-style way she says, “Next chapter!”

Best line: “See me nervously pulling at my clothes and trying to look busy.”

90. “Invisible String” (2020)

“Cold was the steel of my axe to grind for the boys who broke my heart / Now I send their babies presents” — let the record show that Taylor dropped this line into the world two days after Joe Jonas became a dad. It’s official: she plans literally everything. “Invisible String” revisits some of the places she’s traveled, with a color and a memory for each one, over acoustic finger-picking.

Best line: “Green was the color of the grass where I used to read at Centennial Park.”

89. “How You Get the Girl” (2014)

A seminar on girl hearts and the wooing thereof, with Coach Taylor offering a pep talk to girl-curious boys everywhere. She busts out her trusty acoustic guitar, teardrop stains and all, just to turn it into a beatbox.

Best line: “Stand there like a ghost shaking from the rain / She’ll open up the door and say ‘Are you insane?’”

88. “Renegade,” With Big Red Machine (2021)

Good question, Taylor: “Is it insensitive for me to say, ‘Get your shit together so I can love you?’” She joins her kindred spirits Aaron Dessner and Justin Vernon in their band Big Red Machine, in this highlight from their album How Long Do You Think It’s Gonna Last? “Renegade” is a love story where she’s trying to brighten the world of somebody who’s in love with the darkness. It could be her answer song to the Eagles’ “Desperado,” except with a bit more in the human compassion department.

Best Line: “Is it really your anxiety that stops you from giving me everything? Or do you just not want to?”

87. “Hey Stephen” (2008)

Loaded with classic girl-group flourishes, right from the opening “Be My Baby” drum beat. Plus, it begins and ends with her finest humming solos. If she wanted to hum on every song, she could make that work.

Best line: “All those other girls, well, they’re beautiful/But would they write a song for you?”

86. “Babe” (2021)

Taylor wrote “Babe” with Train’s Patrick Monahan, but tossed it to the babes of Sugarland. She sang lethal back-up vocals on their 2018 hit version — not to mention playing the femme-fatale supervillain in the Mad Men-style video. But it was worth the wait to get her own version on Red (Taylor’s Version), with Tay lingering over the “promises, promises” hook.

Best line: “This is the last time I’ll ever call you ‘babe.’”

85. “Anti-Hero” (2022)

Taylor should begin more songs with the line “I have this thing where…”, right? She has LOTS of this thing. “Anti-Hero” addresses her public persona, in the tradition of Taylor Lead Singles, as opposed to her private or creative life, with self-deprecating quips in every verse, and the sing-along chorus: “It’s me! Hi! I’m the problem, it’s me!”

Best line: “Sometimes I feel like everybody is a sexy baby / And I’m the monster on the hill.”

84. “Should’ve Said No” (2006)

A pissed-off highlight of the debut, with an Oasis-worthy chorus. Savor the perfect Liam Gallagher way she milks the vowels of “begging for forgiveness at my fee-ee-eet.”

Best line: “It was a moment of weakness, and you said yes.”

83. “Vigilante Shit” (2022)

A love triangle that gets lowdown and vicious: “I don’t dress for women / I don’t dress for men / Lately I’ve been dressing for revenge.” The hint of this sexual vigilante seducing her lover’s wife adds a bit of spice, as does the idea of using cosmetics as a fatally glam murder weapon.

Best line: “Draw the cat eye sharp enough to kill a man / You did some bad things but I’m the worst of them.”

82. “White Horse” (2008)

Teen Romantic Tay meets Bitter Adult Tay in a superbly disenchanted breakup ballad that gives up on princesses and fairy tales.

Best line: “I’m not the one you’ll sweep off her feet/Lead up the stairwell.”

81. “Illict Affairs” (2020)

A cheating ballad that can turn me into a godforsaken mess any time. The guitar has a wistful “Last Kiss” tinge, except instead of sneaking peeks at an ex’s social-media photos, it’s all sordid meetings in the parking lot, where all getaway cars end up. The muted regret boils over in the bridge, as she snarls: “Don’t call me kid, don’t call me baby.” The definitive version is from The Long Pond Studio Sessions, with Aaron Dessner stretching out on guitar.

Best line: “Take the words for what they are/A dwindling, mercurial high/A drug that only worked the first few hundred times.”

80. “Mr. Perfectly Fine” (2021)

The opening act of Mr. Casually Cruel, a guy Taylor has kept meeting in her songs ever since. How did she possibly leave a song this strong off Fearless? Because she clearly figured that she needed to save “casually cruel” for an even better song a few years down the road. (One Mr. Casually Cruel wears “a well-pressed suit,” the other wears plaid shirts.) Poor Joe Jonas—now all her exes know that Taylor sends their babies presents, it means there’s a song on the way. “Mr. Perfectly Fine” was the song that truly proved her Taylor’s Version project was for real—the outtakes from her vault weren’t leftovers or juvenalia, but bona fide Swift songs. Never be so casual you forget to be cruel; never be so cruel you forget to be casual.

Best line: “Sashay away to your seat/It’s the best seat in the best room.”

79. “You’re On Your Own Kid” (2022)

A New Order-like synth-pop tale of teenage isolation: another teenage girl from a wasteland of a home town, dreaming of getting out or running away, but using music and art and writing to create her own fantasy world.

Best line: “I searched the party of better bodies / Just to learn that my dreams aren’t rare.”

78. “Come Back…Be Here” (2012)

A yearning prayer for a rock & roll boy on tour, weak in the knees as she pleads for him to jet back on any terms he chooses.

Best line: “I guess you’re in London today.”

77. “Teardrops on My Guitar” (2006)

One of her defining early smashes – and the one that marked her crucial crossover to the minivan-mom adult audience, where country stars do most of their business. It also inspired the first anti-Taylor answer song – Joe Jonas sang, “I’m done with superstars/And all the tears on her guitar” in 2009, on the JoBros’ instantly forgotten Lines, Vines and Trying Times. She added a P.S. years later in “Invisible String,” after she and Joe became friends again — proof that her songs just go on rewriting themselves.

Best line: “Drew walks by me / Can he tell that I can’t breathe?”

76. “Sad Beautiful Tragic” (2012)

She must have heard a Mazzy Star song on the radio that morning and thought, “Hey, this sounds like fun.” All the details are in place, from her woozy Hope Sandoval mumble to the way it nails Sandoval’s exact tambourine sound. Such an underrated Red gem, one she’s almost never sung live, but it was one of her templates for the sound of Folklore — Mazzy Swift rights forever. Would any other songwriter on Earth have the sheer gall to get away with that title? Let’s hope nobody tries.

Best line: “You’ve got your demons, and, darling, they all look like me.”

75. “It’s Nice to Have a Friend” (2019)

The most divisive track on Lover — but for those of us who cherish this song, it’s a tiny little haiku miracle. That harp. Those steel drums. That creepy Lost Boys choir. That “Moonlight Mile” guitar. The childhood vibe evokes the White Stripes’ “We’re Going to Be Friends,” but it’s all her. Also, love how this story starts with a lost glove — seven years after the lost scarf in “All Too Well.”

Best line: “Call my bluff / Call you ‘babe.’”

74. “I Did Something Bad” (2017)

https://www.youtube.com/watch?v=3CBhrZf2AKM

Wait, she fell in love with a narcissist? Who saw that coming? Despite the Eurodisco bleeps and bloops, this is a total Nineties grunge-rock rager – she switches into Eddie Vedder/Scott Weiland mode when she growls that “over and over and over again if IIII could.” This is just waiting for her to turn it into a head-banging live guitar monster.

Best line: “I never trust a playboy but they love me / So I fly ’em all around the world and I let them think they saved me.”

73. “Mine” (2010)

“You made a rebel of a careless man’s careful daughter” is one of those hooks where she seems to cram a whole life story into one line.

Best line: “I was a flight risk with a fear of falling.”

72. “The Lakes” (2020)

Let’s face it: Swift has trained us to expect the unexpected, but nobody guessed she’d crown Folklore with the best song ever about 19th century Romantic poets. (Only competition: Van Morrison’s “Summertime in England.”) In “The Lakes,” she wanders the Windermere Peaks in the footsteps of William Wordsworth and Samuel Taylor Coleridge. It’s her answer to Wordsworth’s “Tintern Abbey,” as she roams the wide open spaces so she can listen to “the still sad music of humanity.” As a Wordsworth fanatic, I’m grateful this song exists (“Peele Castle” Hive, rise!) and Tay should keep it going with the lit fan-fic — maybe Emily Dickinson or Gertrude Stein next?

Best line: “I want auroras and sad prose/I want to watch wisteria grow.”

71. “The Man” (2019)

Imagine a timeline where Taylor released this as the first single from Reputation, instead of “Look What You Made Me Do.” It’s safe to say people might have gotten the message faster. “The Man” is the sharpest feminist anthem she’s written (so far). The unspoken subtext: If these dudes had to spend a day in her shoes, they’d crumble like a soggy chunk of feta cheese.

Best line: “When everyone believes you, what’s that like?” Listen here.

70. “Cowboy Like Me” (2020)

Taylor never really had a thing for cowboys, even in her country days, so it makes sense she’d rather be the cowboy than rope one for herself. She’s a grifter swindling her sugar daddies, until she falls for a fellow con artist. But they don’t know if they can give up the thrills of the chase — the same old dilemma of “you love the players and you love the game.” Aaron Dessner’s guitar adds the right touch of country-rock. “I’m waiting by the phone like I’m in an airport bar” is one of the best old-media jokes on an album that also has centerfolds and VHS tapes.

Best line: “The skeletons in both our closets plotted hard to fuck this up.”

69. “Wildest Dreams” (2014)

You rang, Goth Taylor? At first this might have seemed like a minor pleasure on 1989, but it really sounds stronger and stronger over the years, especially when she hiccups the words “my last request ih-is.” The video features giraffes and zebras.

Best line: “He’s so tall and handsome as hell/He’s so bad, but he does it so well.”

68. “I Bet You Think About Me,” With Chris Stapleton (2021)

This rowdy hell-raising saloon sing-along about a rich ex is a delightful honky-tonk jam — the kind of straight-up Nashville vibe she was about to leave behind. In the classic “Friends in Low Places” country tradition, she taunts him for his “organic shoes” and “cool indie music concerts.” Which in 2012 meant he was into the National and Bon Iver.

Best line: “The girl in your bed has a fine pedigree/And I bet your friends tell you she’s better than me.”

67. “Daylight” (2019)

The finale of Lover, and a passionate sequel to “Clean.” “Daylight” takes off in the final minute when she gives a soliloquy that sounds like one of those 2 a.m. voice memos you forget about until you find them on your phone weeks later. “I wanna be defined by the things I love, not the things I’m afraid of” — it’s an affirmation to believe in.

Best line: “I once believed love would be burning red, but it’s golden.”

66. “Dress” (2017)

Swift is no stranger to getting emo over her dresses, but this time it’s different: “Only bought this dress so you could take it off.” Her most carnal slow jam is also one of her saddest – the ache in her voice, the yearning in those synth sparkles. There’s something so “Little Red Corvette” in the way she interrupts her own wordplay with forlorn sighs. As for that golden tattoo – hold on, we’re going home.

Best line: “I don’t want you like a best friend.” Listen here.

65. “This Love” (2014)

A meditative 1989 nocturne – half acoustic introspection, half electro reverie – as she genuflects in the midnight hour.

Best line: “I could go on and on, on and on/And I will.”

64. “Forever Winter” (2021)

“Too young to know it gets better” is an empathetic hook from a songwriter just moving into her twenties. “Forever Winter” is a Red vault outtake where she’s worried about a troubled friend, wishing she could protect them from their tribulations. It makes a companion to a very different 2021 tune: her Big Red Machine single “Renegade,” another song about the mechanics of compassion.

Best line: “He spends most of his nights wishing it was how it used to be/He spends most of his flights getting pulled down by gravity.”

63. “Mastermind” (2022)

The flip side of “Enchanted”: in this story Taylor is the chess master of love, plotting out every move in advance until her prey falls right into her logical trap. Love how she says, “Checkmate! I couldn’t lose.” Since Taylor recently revealed that the final scene of her “All Too Well” short film was inspired by Barbara Stanwyck in Stella Dallas, “Mastermind” could be Stanwyck in The Lady Eve, as the grifter scheming to destroy Henry Fonda’s life. (The Swift/Stanwyck connections go so deep.) 

Best line: “I’m only cryptic and Machiavellian because I care.”

62. “Treacherous” (2012)

“Put your lips close to mine/As long as they don’t touch” – now there’s an entrance line. Taylor braves the ski slopes of love, with a seething acoustic guitar that finally detonates halfway though. A weird sonic detail: if you play this immediately after Joni Mitchell’s “People’s Parties,” the transition is almost frighteningly perfect.

Best line: “Nothing safe is worth the drive.”

61. “‘Tis the Damn Season” (2020)

A Hollywood girl who’s too shiny for her tiny hometown — the loudest woman this town has ever seen — comes back for the holidays, staying with her parents, and falls right back into the arms of the boy she left behind. Dorothea realizes she doesn’t really fit in either place, but she’ll soon be heading back to her bitch-pack of fair-weather friends in L.A. The best U2-style guitar on a Swift song since “State of Grace.”

Best line: “The road not taken looks real good now/Time flies, messy as the mud on your truck tires.”

60. “Ronan” (2012)

A little-known charity single for cancer research, unlike anything else in her songbook. She wrote this about Ronan Thompson, a four-year-old Arizona boy who died of neuroblastoma, after she read his mom’s blog. She turned the blog posts into an eloquent ballad (crediting Maya Thompson as co-writer) and performed “Ronan” at the Stand Up to Cancer benefit. You might expect it to be manipulative and obvious; it isn’t. It’s emblematic of the kind of narrative she could keep doing for decades to come — an early run for her Folklore and Evermore character studies. She sings it with even more soul on Red (Taylor’s Version).

Best line: “What if the miracle was getting even one moment with you?”

59. “Happiness” (2020)

The saddest song on her saddest album — so what else would she call it but “Happiness”? Taylor’s lifelong romance with The Great Gatsby pays off here, when she quotes Daisy Buchanan and sings, “I hope she’ll be a beautiful fool.” And “I haven’t met the new me yet” is a poignant line from a songwriter who’s collected so many New Mes over the years. She also sings about “the dress I wore at midnight” — bet that’s the same party dress she’s wearing in “The Moment I Knew,” a song about getting stood up on her 21st birthday. Taylor released this exactly ten years after that night, just in time for her 31st birthday. The lesson, as always: she plans everything.

Best line: “I pulled your body into mine every goddamn night/Now I get fake niceties.”

58. “Safe and Sound,” With the Civil Wars (2012)

This hidden jewel took on a whole new luster after it became her blueprint for Folklore and Evermore. “Safe and Sound” ventures into rootsy folkie territory, on the Hunger Games soundtrack. She explores crevices in her voice she’d never opened up before, teaming up with the Civil Wars and producer T-Bone Burnett. The Swift-Burnett connection raises the question of how long it’ll take her to collaborate with Elvis Costello, a songwriter with whom she shares some fascinating affinities. At the very least, Tay should cover “New Lace Sleeves.”

Best line: “Don’t you dare look out your window, darling/Everything’s on fire.”

57. “My Tears Ricochet” (2020)

What a ghostly scene: a spectre watches her funeral, haunting her enemies, friends, and lovers. “I didn’t have it in myself to go with grace” — maybe not a huge surprise. One of her spookiest Goth Tay ballads, especially when she admits, “I still talk to you,” and the ghost choir adds, “When I’m screaming at the sky.”

Best line: “If I’m dead to you, why are you at the wake cursing my name?

56. “Mean” (2010)

A banjo-core Tay-visceration of people who are mean, liars, pathetic, and/or alone in life, including the ones who live in big old cities. Always a live highlight on her early tours, showcasing her murderers’ row of a band, the Agency.

Best line: “Drunk and grumbling on about how I can’t sing.” Listen here.

55. “I Knew You Were Trouble” (2012)

It slams like a lost Blondie hit, from somewhere between Parallel Lines and Eat to the Beat. The way she sings the word “drown-i-i-i-ing” alone makes it.

Best line: “He was long gone when he met me/And I realize the joke is on me.” Listen here.

54. “Sweet Nothing” (2022)

It’s a long road through pop history from 1950s teen country star Brenda Lee chirping “Sweet Nothin’s” to the Velvet Underground chronicling street-punk existential despair in “Oh! Sweet Nuthin’.” But Taylor connects all the dots along the way. “Sweet Nothing” is her portrait of domestic bliss, co-written with “William Bowery” a.k.a. boyfriend Joe Alwyn. Love the moment where she writes a poem on the way home and he marvels, “What a mind.” Like so many of her finest love songs, it’s about finding the courage to stop hiding behind distractions, and letting yourself be seen.

Best line: “Industry disrupters and soul deconstructers / And smooth-talking hucksters out-glad-handing each other.”

53. “Tim McGraw” (2006)

We knew she was trouble when she walked in – or at least we should have guessed from her debut single. You couldn’t make this up – a nervy high school kid shows up with a country ballad she whipped together after math class one day, about slow dancing in the moonlight to the pickup truck radio: “When you think Tim McGraw/I hope you think of me.” Within a couple of years, she’s an even bigger star than McGraw is.

Best line: “He said the way my blue eyes shined/Put those Georgia stars to shame that night/I said, ‘That’s a lie.’” Listen here.

52. “Ivy” (2020)

An ode to a forbidden extramarital crush, with Taylor raging, “It’s a fire, it’s a goddamn blaze in the dark, and you started it!” “Ivy” has weird musical echoes of the Grateful Dead — those Jerry Garcia-style guitar ripples, or the way the chorus leaps into that “goddamn” a la “Uncle John’s Band.” It shouldn’t be a surprise — Aaron Dessner and his brother Bryce masterminded a great 2015 tribute album, Day of the Dead. (His guitar also goes full Garcia in “Cowboy Like Me.”) Here’s looking forward to Taylor’s Deadhead era — imagine how great her American Beauty will be.

Best line: “The old widow goes to the stone very day/But I don’t, I just sit here and wait/Grieving for the living.”

51. “Call It What You Want” (2017)

Always here for the Taylor castle metaphors. The warmest Rep electro-ballad, about how exotic it feels to give up worrying about judgy strangers and start living a damn life. “Call It What You Want” celebrates a mature relationship — the kind where you turn off your phone for hours at a time and pull down the shades and risk letting yourself get a little known.

Best line: “Not because he owns me / But ’cause he really knows me.” Listen here.

50. “Better Man” (2021)

Taylor gave this one away to Little Big Town, who turned it into a massive 2016 country hit. “Better Man” came to loom large in her legend as a writer, so it was worth the wait to finally get her own proper version. “Better Man” hits even harder with Taylor wailing her tale of adult regret, confessing to the mirror, “The bravest thing I ever did was run.”

Best line: “I gave to you my best/And we both know you can’t say that.”

49. “Bejeweled” (2022)

“Bejeweled” is full of late-night disco jitters, as Taylor sings about the the fear of stepping out onto the floor and putting her heart on display, until she takes the plunge because it’s scarier to think about *not* doing it. It sounds like this could be the neglected wife of “Tolerate It,” finally breaking free. (She boasts, “I polish up real nice,” as opposed to “I polish plates until they gleam and glisten.”) It’s got that “tears on the dance floor” vibe of “New Romantics,” except “New Romantics” was sung by a “we,” yet the singer of “Bejeweled” is feeling very alone indeed. 

Best line: “Sapphire tears on my face / Sadness became my whole sky / Some guy said my aura’s moonstone just ‘cause he was high.”

48. “Sparks Fly” (2010)

“Drop everything now! Meet me in the pouring rain!” Oh, this girl loves her precipitation scenes, but “Sparks Fly” really brings the thunder. It shows off her uncanny power to make a moment sound gauchely private and messily public at the same time. (Waxahatchee has another excellent song called “Sparks Fly” — no relation.)

Best line: “Just keep on keeping your eyes on me.” Listen here.

47. “22” (2012)

Approximately 22,000 times more fun than actually being 22. The best song about turning the double deuce since Neil Young’s “Powderfinger,” if not the Stratford 4’s “Telephone,” it’s also her first shameless disco trip, with that Nile Rodgers-style guitar flash. But the power move is that “uh oh” into the chorus – the oldest trick in the book, except she makes it sound brand new every time.

Best line: “This place is too crowded, too many cool kids.” Listen here.

46. “Hits Different” (2022)

https://www.youtube.com/shorts/uhjx7FemU6o

The bonus track from Midnights is a breezy departure from the rest of the album, with sun-kissed California rock guitar and wildly funny lines about why Taylor is your ultimate Argumentative Antithetical Dream Girl. “Hits Different” sounds like it could be Betty or James a couple years down the line, after one of them skips town like an asshole outlaw. “I never don’t cry at the bar” feels like the truth. But “I don’t need another metaphor” is the funniest lie in the song, since Taylor loves piling up metaphors even more than she loves crying in bars. 

Best line: “Each bar plays ‘Our Song’ / Nothing has ever felt so wrong.”

45. “Style” (2014)

Not always a subtle one, our Tay. This extremely 1986-sounding synth-pop groove is full of hushed-breath melodrama, where even the guy taking off his coat can feel like a plot twist. (Why would he keep his coat on? This is his apartment.) And the long-running songwriting badminton between her and Harry Allegedly is pop call-and-response the way it ought to be – no matter how much misery it might bring into their personal lives, for the rest of us it means one great tune after another.

Best line: “You got that James Dean daydream look in your eye/And I got that red lip classic thing that you like.” Listen here.

44. “State of Grace” (2012)

She opens Red with one of her grandest love songs in arena-rock drag, and the U2 vibe makes sense since she’s also got a red guitar and the truth. The acoustic version was always a welcome bonus track on the expanded Red, but it sounds even more autumnal now on Taylor’s Version. If “State of Grace” is her U2 song, what’s the U2 song that sounds most like Taylor? Probably “All I Want Is You,” though you could make a strong case for “A Sort of Homecoming.”

Best line: “Up in your room and our slates are clean/Twin fire signs, four blue eyes.” Listen here.

43. “Willow” (2020)

“Take my hand, wreck my plans, that’s my man” is a great hook from the songwriter who turns plan-wrecking into an art form. “Willow” is the perfect song to introduce Evermore, all rustic guitar and spooky romance, deep in the woods. Taylor really committed to the concept at the Grammys, singing “Willow” on the roof of a moss-covered cabin. In the video, she gazes at her reflection in a pool like Narcissus, and like she once sang, the narcissists love her. Heartbreak: the Nineties trend that always comes back strong.

Best line: “Show me the places where the others gave you scars.”

42. “Betty” (2020)

The Betty/Inez/James love triangle is at the heart of Folklore, inspiring three of its best songs. Every aspect of “Betty” sounds designed to explode when she finally gets to take it to the stage, from the “Thunder Road” harmonica to the most shameless lighters-up key change of her career. Picture all the beer that will get sloshed on you when it’s So I Showed Up To Your Party o’clock. (Her live version at the Academy of Country Music Awards in September 2020 was an arena-rock blast, for the year with no arenas.) Also love how when Taylor steps into the mind of a 17-year-old boy, the first thing she fantasizes about his male privilege is the right to make unchallenged assumptions. If James is a boy, that is. (Taylor takes care to leave it open — but has any boy in her songs ever stopped at a streetlight?) Key question: Was James in his car driving around the party listening to 1989? Because he follows all the advice she gives in “How You Get the Girl” and (surprise) it works.

Best line: “Will you kiss me on the porch in front of all your stupid friends?”

41. “Begin Again” (2012)

“You said you never met one girl who had as many James Taylor records as you,” indeed. Sweet Baby Tay drops a deceptively simple ballad that sneaks up and steamrolls all over you, as an unmelodramatic coffee date leads to an unmelodramatic emotional connection. She’s always been outspoken about her mad love for her namesake JT and Carly Simon, but “Begin Again” could be the finest collabo they never wrote.

Best line: “You don’t know why I’m coming off a little shy/But I do.” Listen here.

40. “Fearless” (2008)

Oh Fearless, it’s easy to take you for granted sometimes. The first time I heard her sophomore record (the record company literally played it over the phone for me because they were so afraid of it leaking) I thought, “Holy cats, this is a perfect pop album. She’ll never top this.” Then she topped it seven times in a row, to the point where it became one of history’s most curiously overlooked perfect pop albums. But Fearless has a whole new mystique ever since she chose it to kick off her remake series. The title anthem gathers so many of her favorite tropes in one chorus—rain, cars, fancy dresses, boys who stare at her while driving instead of watching the damn road, shy girls posing as brave and faking it till they make it—and builds up to a swoon. But it soars even higher now in Taylor’s Version, with all the adult soul in her voice

Best line: “You’re just so cool, run your hands through your hair/Absent-mindedly making me want you.” Listen here.

39. “Getaway Car” (2017)

One of Swift’s most endearingly McCartney-esque traits is the way she goes overboard with her latest enthusiasm and starts Tay-splaining it as her personal discovery. On 1989, she informed us all what New York is; on Reputation, she breaks down the concept of “alcohol.” (Wait, you can drink beer out of plastic cups? Tell us more!) Hence “Getaway Car,” where Film Noir Tay makes her big entrance, knocking back Old Fashioneds at the motel bar, a femme fatale playing two fall guys against each other. In the glorious final minute, she decides to sell them both out and speeds off to her next emotional heist.

Best line: “Nothing good starts in a getaway car.” Listen here.

38. “Snow On The Beach” feat. Lana Del Rey (2022)

“Weird but fucking beautiful,” indeed. “Snow On The Beach” is a duet with Lana Del Rey, although it sounds all the way Swiftian vocally, lyrically, and (especially) melodically. The most beguiling tune on Midnights, with pizzicato strings and lines about falling for a lover bright enough to burn out your periphery. That melody is damn near impossible to dislodge from the skull, especially that soft “it’s coming down, it’s coming down” at the end. 

Best line: “Life is emotionally abusive.”

37. “Cornelia Street” (2019)

A ballad about how scary it is to realize how much you have to lose — how the brand-new-crush tingle of “Holy Ground” eventually turns into the place where you have to build a life. She looks around an apartment where she’s memorized every creak in the floor, a neighborhood full of romance, and comprehends how fast it all could turn into a heartbreak hotel.

Best line: “Baby, I get mystified by how this city screams your name.” Listen here.

36. “Nothing New,” With Phoebe Bridgers (2021)

Taylor and Phoebe are the Ghostface and Raekwon of the Sad Girl agenda — two kindred spirits blending their voices for a mournful guitar ballad of getting older, losing your novelty, but still crying in your bedroom. “Nothing New” is the vault track everybody was fiending for from Red (Taylor’s Version) — but it’s even better than we were hoping. The eternal question: “How can a person know everything at 18, and nothing at 22?” As you can tell from Folklore, Evermore, and Punisher, these two know the ingenue blues inside out. Can we please get a whole Taylor-Phoebe duet album?

Best line: “They tell you when you’re young/‘Girls, go out and have your fun’/Then they hunt down and kill the ones who actually do it.”

35. “Last Kiss” (2010)

Toward the end of Speak Now, when you’re already wrung out from sad songs and begging for mercy, this six-minute quasi-doo-wop ballad creeps up on you to inflict more punishment. One of those flawless Nathan Chapman productions – so sparse, so delicate, flattering every tremor of her voice.

Best line: “I’m not much for dancing, but for you I did.” Listen here.

34. “Cardigan” (2020)

The sweater left behind under someone’s bed, like the lost scarf in “All Too Well” or the lost glove in “It’s Nice To Have a Friend.” (Or the ex-wife’s dress left in the closet in Fiona Apple’s “Ladies”?) Swift sorts through the memories that go with breathing in the scent of a remembered lover, over brooding piano. “I knew you, leaving like a father, running like water” sure jumps out of the song, as startling as the “careless man’s careful daughter” in “Mine.” The day she wrote this song with the National’s Aaron Dessner, she posted a photo with the caption, “Not a lot going on at the moment.” Why do we ever believe a word she says?

Best line: “Chase two girls, lose the one / When you are young they assume you know nothing.”

33. “Our Song” (2006)

The hit that made me a Swift fan, the first moment I heard it in 2007 – it knocked me sideways in the middle of lunch. (The CW played it as interstitial music between afternoon reruns of the Clueless sitcom and What I Like About You.) “Our song is a slamming screen door,” what a genius hook. I Googled to see who wrote this; it turned out the songwriter was also the singer and – how strange – she was just starting out. I hoped she might have at least another great tune or two in her. This song and that voice have kept slamming those screen doors ever since.

Best line: “We’re on the phone, and you talk reeeeealslow/’Cause it’s late and your mama don’t know.” Listen here.

32. “Evermore” (2020)

Taylor’s title tracks are usually bangers, but “Evermore” is a pensive piano meditation where she sits alone by the fireside, trying to figure out how it all went so wrong. We know Tay grew up a hardcore Def Leppard fan, so it’s no surprise the piano here echoes “Hysteria,” their saddest and most proto-Swiftian hit. (She sang a fantastic “Hysteria” with them on CMT in 2008.) Bon Iver’s Justin Vernon joins for the call-and-response bridge. Love the half-chuckle in the line “it was real enough to get me through”: the closest she comes to one of her Taylor Laughs in the Folklore/Evermore era.

Best line: “I rewind the tape, but all it does is pause.”

31. “Red” (2012)

The mission statement for Red, this century’s most ridiculously masterful megapop manifesto. Eurodisco plus banjos – the glitter-cowgirl totality Shania Twain spent years trying to perfect, with a color-tripping lyric worthy of Prince Himself, faster than the wind, passionate as sin. Plus, her all-time gnarliest pileup of Swiftian metaphors. (Nitpick: What kind of crossword puzzle has no right answer? What self-respecting puzzlemaster would sign off on that?)

Best line: “Lovin’ him is like driving a new Maserati down a dead-end street.” Listen here.

30. “Would’ve, Could’ve, Should’ve” (2022)

Taylor revisits the memory of her teenage self, with an adult sense of compassion. “Would’ve, Could’ve, Should’ve” is a powerful sequel to “Dear John,” but when she sang about this story before, her tone was more straightforward anger and regret. This song is messier, more confused, more ambivalent, as she struggles to understand the brash, complex 19-year-old artist/superstar/mirrorball she used to be. As she reflects, “I would have stayed on my knees / And I damn sure never would’ve danced with the devil at 19 / And the God’s honest truth is that the pain was heaven.”

Best line: “If I was some paint, did it splatter on a promising grown man?”

29. “Champagne Problems” (2020)

In the Swiftian universe, girls have fathers — and extremely heavy relationships with them — but boys rarely have mothers. The guy in this song has a mom and a sister — you have to go back to the scarf in Maggie Gyllenhall’s closet to find a guy with either one, let alone both. The sister in “Champagne Problems” gets only one line, but she’s the one with the actual champagne. (What can it mean that “Our Song,” one of her first hits, still has her scariest boyfriend’s-mama character?) So it’s fitting Taylor echoes the “All Too Well” piano chords for this tale, where a woman responds to her college boyfriend’s marriage proposal by blowing up her life along with his. She sees herself through the eyes of his family, their dorm friends, his hometown skeptics — but she realizes she can’t see herself in this picture at all.

Best line: “She would have made such a lovely bride/What a shame she’s fucked in the head.”

28. “Ours” (2010)

Like so many of her songs, “Ours” sounds like it could be channeling the 16-blue mojo of the Replacements’ punk-rock bard Paul Westerberg. (Melodically, it evokes “When It Began,” though it feels more like “I Will Dare.”) Especially the best line, which is possibly the best-est “best line” on this list, and which I sing to myself a mere dozen times a day.

Best line: “Don’t you worry your pretty little mind/People throw rocks at things that shine.” Listen here.

27. “Seven” (2020)

Two little girls in the Pennsylvania woods, trying and failing to understand each other. It’s a lost childhood bond (maybe same one from “It’s Nice to Have a Friend”?), from the perspective of a kid too young to recognize that her friend’s angry dad is the ghost in their family’s haunted house. (The traumatizing fathers on Folklore are a plotline in themselves.) The little girls dream of escaping, running away to be pirate twins, but there’s no resolution — just a mystery that gets more confusing she tries to live with it.

Best line: “Please picture me in the weeds, before I learned civility.”

26. “The Archer” (2019)

“The Archer” is the ultimate Goth Tay powerhouse: obsessed with revenge and guilt, shooting poison arrows into her own heart, still trying to settle the score after the battle’s over. She’s an emotional Arya Stark who never gets to cross any names off her list, because she always needs to get in one more stab. (Taylor would be wiping the blood off her sword saying, “Oh, and another thing.” That’s why we relate, right?) One of the most hair-raising moments in her music: when she switches from “they see right through me” to “I see right through me!”

Best line: “All of my heroes die all alone / Help me hold on to you.” Listen here.

25. “We Are Never Ever Getting Back Together” (2012)

Like, ever. Her funniest breakup jam, because it’s her most self-mocking. She could have made the guy in this song a shady creep—a cheater, a liar, a scarf-stealer, etc. But, no, he’s just a needy little run-of-the-mill basket case, exactly like her, making the same complaints about her to his own bored friends, though his complaints can’t be as catchy as this chorus. And the video is a gem, especially when she’s wearing the Tay Is Seriously Mad Now glasses. Where is that indie-rock bar that still has a pay phone?

Best line: “And I’m like, I mean, this is exhausting, OK?” Listen here.

24. “Maroon” (2022)

A New York romance where all the heartache she feared in “Cornelia Street” comes true, leaving her haunted by a love that was burning red. At first, she’s dancing barefoot, drinking on the roof, asking, “How’d we end up on the floor anyway? / You say, ‘Your roommate’s cheap-ass screw-top rosé, that’s how.’” The lovers celebrate having this big wide city all to themselves. But after it falls apart (in the usual way), she’s surrounded by the wreckage. All the different shades of maroon appear in her dreams—the wine stain on her t-shirt, the sunset, the funeral carnations, the lips she used to call home. “Maroon” has some of Taylor’s most pained singing on Midnights, especially when she sighs, “I awake with your memory over me / That’s a real fucking legacy.” “Maroon” feels so linked to “Bigger Than The Whole Sky”—ballads about how mourning can feel like both a blessing and a curse.

Best line: “When the morning came / We were cleaning incense off your vinyl shelf.”

23. “New Year’s Day” (2017)

What a twist: the one-time poet laureate of teen crushdom turns out to be even sharper at adult love songs. “New Year’s Day” is her hushed piano-and-guitar ballad about two people waking up the morning after the party and getting back to the reality they share together. It captures the romance of mundane domestic details – sweeping up the glitter, rinsing out bottles, realizing this total nothing of a day is a memory you will cherish long after you’ve both forgotten the party. This is the kind of song she could keep writing into her forties and fifties.

Best line: “Please don’t ever become a stranger whose laugh I could recognize anywhere.” Listen here.

22. “This Is Me Trying” (2020)

How rude of Ms. Swift to write a song so full of lines I need to get carved on my tombstone — except it would take three or four tombstones to hold them all. The easiest Folklore song to underrate, because it seems so deceptively straight-ahead. But as in “Mirrorball,” the album’s other try-try-try song (also the other “I want you to know” song), her vocal goes right to the heart. Love the deadpan way she shrugs “I have a lot of regrets about that,” plus her very on-brand decision to sing the song in somebody’s doorway. “I was so ahead of the curve, the curve became a sphere” — what a math flex. Fact: Taylor could have invented geometry, but Euclid couldn’t have written this song.

Best line: “They told me all of my cages were mental/So I got wasted like all my potential.”

21. “Coney Island” (2020)

Twelve miles from Cornelia Street, but it feels a lifetime away. “Coney Island” is her duet with the National, trading verses with singer Matt Berninger, for an Evermore highlight that picks up the story from Folklore. “Coney Island” sounds like the “August” girl left her small town, forgot about James and Betty, moved to New York, found a hipster boy, figured everything would be different in the big old city, then found herself stuck in the same old story all over again. When you’re a grown-up, they assume you know nothing.

Best line: “We were like the mall before the Internet/It was the one place to be/The mischief, the gift-wrapped suburban dream.”

20. “The Great War” (2022)

One of the stellar Aaron Dessner collaborations tucked away on the Midnights 3 A.M. Edition. “The Great War” comes clean about the side of Taylor who only wants love if it’s torture, going into the question of how emotional battles happen and how to end them, especially when you realize you’re the one firing the cannons. It’s a dilemma she’s written about honestly her whole career, from her teen ballad “Cold As You” (“I start a fight because I need to feel something”) to “Afterglow.” The World War One imagery and martial drums are fitting for a song about how easy it is for two hearts to dig themselves into trenches. But  “The Great War” also doubles as a tribute to the type of lover who can help rescue you from your own destructive instincts, the kind you want on your side. 

Best line: “My knuckles were bruised like violets / Sucker-punching walls / Cursed you as I sleep-talked.”

19. “Clean” (2014)

Love is the drug. “Clean” is the stark synth-folk ballad of an infatuation junkie struggling through some kind of detox, with a big assist from Imogen Heap. An intense finale for the all-killer homestretch of 1989.

Best line: “Ten months sober, I must admit/Just because you’re clean don’t mean you don’t miss it.” Listen here.

18. “The Last Great American Dynasty” (2020)

There goes the loudest woman this town has ever seen. So many heroic witches, widows, crones, and madwomen on Folklore, but this one steals the show. “The Last Great American Dynasty” initially seemed more a gimmick than a song, with a clever twist that would wear off fast. But the intricate details just grow over time — melodically, production-wise, most of all vocally. Taylor’s in a haunted house where Rebekah is just one of the madwomen in the attic, and the ghosts make her feel right at home. Imagine singing “marvelous” in one song in 2012, tucking the word in your back pocket for the revenge sequel, then waiting eight years for the right moment to play that ace. Dali or no Dali, this woman will never lose a card-game bet in her damn life.

Best line: “I had a marvelous time ruining everything.”

17. “Labyrinth” (2022)

Not the flashiest song on Midnights—there’s no fancy metaphor, no razzle-dazzle wordplay, no plot, no clever twist. Just her most painfully gorgeous melody, massive in its simplicity. Taylor spends most of “Labyrinth” just sighing, “Uh oh, I’m falling in love,” over neon synths that flicker and splutter like the circuits are melting down. She doesn’t lean on poetics here—the word “labyrinth” appears only once, when she sighs, “Lost in the labyrinth of my mind.” It’s one of Jack Antonoff’s craftiest productions—loads of Brian Eno circa Another Green World. [https://www.youtube.com/watch?v=2Tqy6be0Juc] Every “uh oh” and “oh no” hits so hard—she slides into each one from a different angle. If you’re ever in the mood to forget about Taylor the songwriter and just savor her as one of pop’s most brilliant vocalists, “Labyrinth” is one to cherish. It takes some nerve for her to use this Borgesian title for such a deceptively minimal tune, but this is a lavender labyrinth you can get happily lost in. A stealth classic. 

Best line: “Breathe in, breathe through, breathe deep, breathe out.”

16. “Enchanted” (2010)

The moment where this bittersweet symphony leaps from a nine to a 10 comes at the 4:25 point, when it feels like the song has reached its logical conclusion, until the Interior Monologue Voice-Over Taylor beams in to whisper: “Please don’t be in love with someone else/Please don’t have somebody waiting on you.” In the final seconds, for the coup de grace, she duets with herself.

Best line: “The lingering question kept me up/ 2 a.m, who do you love?” Listen here.

15. “Fifteen” (2008)

“In your life you’ll do things greater than dating the boy on the fohttps://www.youtube.com/watch?v=S4PuN-IWi2gotball team / I didn’t know that at 15.” Still south of her twenties, she sings her compassionate, sisterly yet hard-ass advice to her fellow teenage girls. (Spoiler: boys are always lying about everything.) Childhood pal Abigail Anderson will always be her coolest BFF of all time; Taylor was a bridesmaid in her wedding just a few years ago.

Best line: “We both cried.” Listen here.

14. “Holy Ground” (2012)

Nobody does zero-to-60 emotional peel outs like our girl, and “Holy Ground” is her equivalent of Evel Knievel jumping the Snake River Canyon. Note the sly brilliance of how she steals that Eighties guitar riff from none other than Billy Idol, making this her “White Wedding” as well as her “Rebel Yell.” (Though the lyrics are about dancing with herself.) A highlight on the Red tour, showcasing Tay’s drum-solo skills.

Best line: “Hey, you skip the conversation when you already know.” Listen here.

13. “Bigger Than The Whole Sky” (2022)

It’s rare to hear Taylor begin a song by admitting she’s at a loss for words—and mean it. But that’s what makes “Bigger Than the Whole Sky” so powerfully understated. It’s a twangy grief ballad, burrowing into the elegiac Mazzy Star vibe of “Sad Beautiful Tragic,” ten years after it was a forgotten highlight of Red. She mourns a goodbye that came too soon, without trying to describe what’s been lost or what kind of future is ending. But Jack Antonoff’s slide guitar eloquently fills in for all the missing details. At the end, she tries to rationalize her loss by shrugging that “it’s not meant to be,” but then rips that cliché apart as a lie she refuses to believe. Some things are meant to be, but aren’t, and those can be the toughest to mourn.

Best line: “Every single thing I touch becomes sick with sadness.” 

12. “Right Where You Left Me” (2021)

Okay, so we already know Taylor gets a kick out of leaving great songs off the album — but this is ridiculous. Maybe even criminal. Yet perhaps “Right Where You Left Me” had to be a bonus track on Evermore, because hearing this song once means putting it on repeat and shutting down the flow of the album. A decade after Taylor was feelin’ 22, she gets trapped in 23, reliving the moment she got her heart broken, still sitting in that restaurant. (The same one where they had their first date in “Begin Again”?) Every time she gulps “you left me noooo,” it sounds more desperate, riding Aaron Dessner’s obsessive banjo hook. She feels paralyzed in the past, but his banjo keeps urging her to get running while she can. “Right Where You Left Me” is the only Swift song with an actual cry for help — twice — and it’s a startling sound. Repeat: she left this off the album.

Best line: “Did you ever hear about the girl who got frozen?/Time went on for everybody else, she won’t know it/She’s still 23, inside her fantasy, how it was supposed to be.”

11. “Cruel Summer” (2019)

For the first 98 seconds, “Cruel Summer” is merely a perfect Taylor Swift song. Then for the bridge, she takes off into a deranged greatest-hits album’s worth of choruses from brilliant songs she hasn’t written yet. You could write a whole dissertation on the erotics of windows in Taylor’s songs — no poet since Keats has been so obsessed with the kind of desire that doesn’t dare use the door. “Cruel Summer” is about sneaking around and feeling ashamed of her secrets, but also feeling proud of how ashamed she is, until she finally yells her dirtiest secret out loud: “I love you — ain’t that the worst thing you ever heard?” But make no mistake, she loves her secrets more than she’ll ever love this paramour.

Best line: “I snuck in through the garden gate / Every night that summer just to seal my fate.” Listen here.

10. “Dear John” (2010)

A slow-burning, methodical, precise, savage dissection of a failed quasi-relationship, with no happy ending, no moral, no solution, not even a lesson learned – just a bad memory filed away. “Dear John” might sound like she’s spontaneously pouring her heart out, but it takes one devious operator to make a song this intricate feel that way. (“You are an expert at sorry and keeping lines blurry and never impressed by me acing your tests” – she makes all that seem like one gulp of breath.) Every line stings, right down to the end when she switches from “I should have known” to “You should have known.”

Best line: “I’m shining like fireworks over your sad empty town.” Listen here.

9. “Marjorie” (2020)

The centerpiece of Evermore, an album full of haunted houses and eloquent ghosts. Taylor sings about her late grandmother Marjorie Finlay, an opera singer who used to play the San Juan supper clubs, with the key line, “If I didn’t know better/I’d think you were singing to me now.” Her hushed voice tells the story over pulsing vintage synths, in the minimalist mode of Steve Reich’s Music for 18 Musicians. At the end, she samples Marjorie’s soprano voice. A song about getting to know your loved ones better after they’re gone, giving them a home in your memory, turning their lives into folklore and passing them on like folk songs.

Best line: “Never be so kind you forget to be clever/Never be so clever you forget to be kind.”

8. “Blank Space” (2014)

A double-venti celebration of serial monogamy for Starbucks lovers everywhere, as Tay zooms through the whole cycle – the high, the pain, the players, the game, magic, madness, heaven, sin. Every second of “Blank Space” is perfect, from the pen clicks to the “nasss-taaaay-scarrr” at the end. The high might not be worth the pain, but this song is.

Best line: “Darling, I’m a nightmare dressed like a daydream.” Listen here.

7. “Lover” (2019)

Ladies and gentlemen, will you please stand? This bombshell is the kind of twangy guitar ballad people thought she didn’t feel like writing anymore, except she’s celebrating the kind of adult passion people assumed wasn’t melodramatic enough for her to bother singing about. But when she hits those high notes in the chorus, it’s like the sensation at the top of the roller coaster when you realize you’re zooming all the way down. “Lover” sounds like a sequel to “Last Kiss,” but with a decade’s worth more soul going into it. She reclaims the cringiest noun in the language and makes it credible for the first time since Prince sang, “I Wanna Be Your Lover.” Great video too, especially when she goes into Sad Blue Violin Pluck mode. Imagine ending your twenties with a song this masterful. Imagine heading into your thirties the same way.

Best line: “With every guitar-string scar on my hand.” Listen here.

6. “Long Live” (2010)

This is her “Common People,” her “Born to Run,” her “We Are the Champions.” An arena-slaying rock anthem to cap off Speak Now, for an ordinary girl who suddenly gets to feel like she rules the world for a minute or two. “Long Live” could be a gang of friends, a teen couple at the prom, a singer addressing her audience. But like so many songs on Speak Now, her secret prog album, it reaches the four-minute point where it feels like it’s over and she’s bringing it in for a landing – except that’s when the song gets twice as great. In the final verse, she makes a gigantic mess. (Actual lyric: “Promise me this/That you’ll stand by me forever.” WTF, girl, you were doing so well there.) Yet that’s the moment that puts “Long Live” over the top – a song nobody else could have written, as she rides those power chords home. That’s Taylor: always overdoing it, never having one feeling where six would do. Long live.

Best line: “I had the time of my life fighting dragons with you.” Listen here.

5. “August” (2020)

“August” feels like such a simple tune, yet it’s one of the craftiest creations in the Swiftian Multiverse. She mourns a summer fling that slipped away like a bottle of wine, over Nineties soft-rock guitars, full of Mazzy Star/Cranberries “late afternoon set at Lilith Fair” energy. (Also, that “do you remember?” at the end seems to beam in straight from LFO’s ‘Summer Girls” — the mark of a truly obsessive pop music scholar.) She tries to kid herself it’s enough to live for the hope of it all, but she keeps running over her same memory again and again, trying to make it add up to something different. It all explodes in the giddy moment at the end, when you think the song is over, and you think she’s finally going to drive away with her head held high, but she circles back for one more “get in the car!” She might sit there alone behind the mall all night, waiting for a lover she knows won’t show up, but she makes it sound like the most romantic possible place to be.

Best line: “So much for summer love and saying ‘us’/Because you weren’t mine to lose.”

4. “Delicate” (2017)

“Is it cool that I said all that?” A little late for that question, Tay. But “Delicate” is her triumph, a whispery vocoder rush that sums up everything she’s about. She steals away for a late-night hoodie-shrouded rendezvous at her local dive bar, trying to play jaded and cool. But because she’s Taylor, she can’t stop constantly pointing out how chill she’s being, elbowing you in the ribs with those “isn’t it? isn’t it?” chants. (I count 24 “isn’t it”‘s in this song and I am feeling every one of them.) She spends “Delicate” talking herself out of that midnight confession, but when it spills out — “I pretend you’re mine all the damn time” – the moment feels cataclysmic. As ever, the girl sets strict emotional rules for herself and then trashes them all. Let’s face it, Tay will always fail spectacularly at playing it cool, because she will never be able to resist saying way too much of All That. Yet as “Delicate” proves, All That is what she was born to say. Isn’t it?

Best line: “Is it chill that you’re in my head?” Listen here.

3. “Mirrorball” (2020)

Taylor shines like the disco ball gazing down on the dance floor, wondering why everybody else looks so confident and imagining how that feels. A seething ballad about a loner feeling a little too loud and a little too bright, afraid everyone’s staring at her flaws yet feeling invisible anyway. “Mirrorball” revisits the party vibe of “New Romantics” from another angle, with Taylor twirling on high heels, spinning like a girl in a brand new dress, hating herself for being so desperate to sparkle for strangers. This is the kind of vulnerable teen sensibility that got her started writing songs in the first place (i.e. most of her debut album). But in classic Swift style, she decides exactly what she’s going to allow herself to feel, then wonders why she feels the exact opposite. She’s the same girl in the swing from “Seven,” grown up yet still feeling like she’s dangling in mid-air, never touching ground. Who else has a songwriting mind like this? Queen of Concept.

Best line: “I’m still a believer but I don’t know why / I’ve never been a natural, all I do is try, try, try.”

2. “New Romantics” (2014)

The way Taylor exhales at the end of the line “I’m about to play my ace-aaah” is perhaps the finest moment in the history of human lungs. “New Romantics” is where she takes the Eighties synth-pop concept of 1989 to the bank, with a mirror-ball epiphany that leaves tears of mascara all over the dance floor. She tips her cap to the arty poseurs of the 1980s New Romantic scene – Duran Duran, Adam Ant, the Human League, etc. – yet sounds exactly like her own preposterously emotional self. (One of my weirdest moments of recent years: explaining this song’s existence to the guys in Duran Duran.) “New Romantics” is hardly the first time she’s sung about crying in the bathroom, but it’s the one that makes crying in the bathroom sound like a bold spiritual quest, which (when she sings about it) it is. The punch line: Having written this work of genius, exceeding even the wildest hopes any fan could have dreamed, she left it off the damn album, a very New Romantic thing to do.

Best line: “We show off our different scarlet letters/Trust me, mine is better.” Listen here.

1. “All Too Well” (2012-2021)

So casually cruel in the name of being awesome. This towering ballad is Swift’s zenith, building to peak after peak. For “All Too Well,” she teams up with her songwriting sensei Liz Rose to spin a tragic tale of doomed love and scarves and autumn leaves and maple lattes. And her greatest song just got even greater in the definitive 10-minute version, with Taylor digging up her lost verses, to bring it to a whole new level of All Too Unwell. What kind of artist takes her own masterpiece and tears it all up? This one. Only this one. Result: an even bolder masterpiece.

Every version of “All Too Well” tells a different story. There’s the “Sad Girl Autumn” version from Long Pond Studio, with Aaron Dessner on piano. The acoustic-guitar solo version from the theater premiere for her short film. But each version feels like it’s all her, because this isn’t really a song about a boy — never was. It’s about a girl, her piano, her memory, and her refusal to surrender her most painful secrets, even when it’s tempting to forget.

 It’s full of killer moments: the way she sings “refrigerator,” the way she spits out the consonants of “crumpled-up piece of paper,” the way she chews up three “all”’s in a row. No other song does such a stellar job of showing off her ability to blow up a trivial little detail into a legendary heartache. That scarf should be in the Rock & Roll Hall of Fame, though in a way it already is. You can schaeden your freude all over the celebrity she reputedly sings about, but on the best day of your life you will never inspire a song as great as “All Too Well.” Or write one.

Best line: “Maybe we got lost in translation/Maybe I asked for too much/Maybe this thing was a masterpiece till you tore it all up/Running scared, I was there, I remember it all too well.” Listen here.

From Rolling Stone US.