100 Greatest Reggaeton Songs of All Time

BY ECLEEN LUZMILA CARABALLO, JON DOLAN, RICARDO DURÁN, KATELINA ECCLESTON, VERÓNICA BAYETTI FLORES, JULYSSA LOPEZ, MOISES MENDEZ II, JENNIFER MOTA, GARY SUAREZ, LUCAS VILLA

NO MATTER HOW you break it down, reggaeton is one of the most popular styles of music on the planet. The genre’s stars are some of the biggest in the industry — Bad Bunny has been the most-streamed artist in the world for two years in a row — and their hits have quickly become international supernovas, played in every country imaginable. Reggaeton is a global phenomenon and a commercial force that’s changed the Latin music business, despite naysayers, and it shows no signs of slowing down.

The genre also represents a rich cultural history, filled with stories of migration, of resistance, and of celebration. The music has deep roots in Panama, where Black communities in the Eighties and Nineties pioneered reggae en español tracks that traveled across the globe and captured people’s imaginations. Those sounds thrived in Puerto Rico, in particular, and bloomed in the island’s underground in the Nineties, cross-pollinating with hip hop scenes in New York and eventually erupting across the world. So many songs — whether they’re classic deep cuts from Playero mixtapes, or record-breaking chart-toppers from more recent years — are a reflection of the genre’s complex stories and intricate evolutions.

Narrowing down the 100 greatest reggaeton songs of all time was no easy feat. The reggaeton canon spans decades and continents, and branches into all kinds of music — bachata, EDM, hip-hop, salsa, and so much more. Some people might debate whether a few songs here belong on a reggaeton list; however, there were some reggae en español, dembow, and underground rap classics by pioneers such as Nando Boom, El General, and Latin Fresh that were so foundational, we found them impossible to keep off.

We also had input from all corners of the music business. To make our list, we put together a panel of critics, experts, and music industry veterans. Those voters included:

Kat Bouza, senior news editor, Rolling Stone
Ecleen Luzmila Caraballo, writer and editor
Jon Dolan, reviews editor, Rolling Stone
Ricardo Duran, Rolling Stone en Español
Katelina “Gata” Eccleston, reggaeton historian
Veronica Bayetti Flores, music journalist
Simon Vozick-Levinson, deputy music editor, Rolling Stone
Julyssa Lopez, senior music editor, Rolling Stone
Jennifer Mota, music historian and journalist
Moises Mendez II, culture reporter
Diego Ortiz, Rolling Stone en Español
Jorge Pabon, Molusco TV
Jerry Pullés, Latin music programmer, Apple Music
AJ Ramos, head of artist partnerships, Latin music and culture, YouTube Music/Google
Maykol Sanchez, head of artist & label partnerships, LATAM & U.S. Latin, Spotify
Gary Suarez, music journalist
Tainy, producer
Lucas Villa, music journalist
Antonio Vázquez, head of U.S. Latin editorial – Spotify
Chente Ydrach, host

The genre is complex; it continues to flourish and thrive in ways that surprise even its biggest fans. Over the years, we’re sure songs will take on new meanings, and new innovations will change the course of the genre. For now, here are Rolling Stone‘s 100 Greatest Reggaeton Songs of All Time.

100. Ozuna feat. Cardi B |’La Modelo’ 2017

By December 2017, Cardi B hadn’t quite become a hip-hop megastar just yet, but was well on her way with hits like “Bodak Yellow.” Still months before unveiling the monster single “I Like It,” the South Bronx rapper linked with Ozuna for a dancehall-tinged cut that melted away all winter vibes and further bolstered New York hip-hop’s ongoing familial connection to reggaeton. —G.S.

99. Zion | ‘Zun Da Da’ 2007

Zion stepped away from the beloved duo Zion y Lennox to record his solo debut, The Perfect Melody, and from the very first song, it was clear he could hold his own. “Zun Da Da” opens with dramatic violins and production that don’t exactly reflect the thudding BPM of reggaeton’s discoteca go-tos, but still capture the tension and yearning of the dance floor. The fact that it’s been sampled — Ivy Queen’s “787” and Zion’s own 2022 track “Tu Amigo” — and remains a classic for DJs and genre-heads alike proves its longevity. —E.L.C.

98. Tomasa del Real feat. DJ Blass | ‘Barre Con El Pelo’ 2018

At a time when artists were toning down reggaeton’s historically explicit lyrics, Tomasa del Real looked to the genre’s nastiest cuts and released “Barre Con El Pelo.” Off her 2018 album, Bellaca del Año, the track is all Auto-Tune, unabashed sexuality, and driving beats, courtesy of genre OG DJ Blass — the perfect recipe for perreo. Though the neo-perreo scene del Real leads can feel uncomfortably separate from mainstream reggaeton, she made sure “Barre Con El Pelo” gave plenty of love and respect to the genre’s origins. —V.B

97. J Balvin, Dua Lipa, Bad Bunny, and Tainy | ‘Un Día (One Day)’ 2020

Having witnessed reggaeton’s many evolutions working with Luny Tunes as a kid, Tainy continues decades later to push the genre into the future. In 2020, the Puerto Rican hitmaker beautifully melded forward-thinking pop with the beats he grew up on by building the dreamy “Un Día (One Day).” Dua Lipa’s voice soars over lofty dembow, while dynamic duo Bad Bunny and J Balvin embrace the electronic soundscape Tainy has laid out for them. The song’s fresh production earned them a Grammy nomination for Best Pop/Duo Performance. —L.V.

96. Enrique Iglesias feat. Descemer Bueno and Gente de Zona |’Bailando’ 2014

The summer of 2014 belonged to Enrique Iglesias. The Spanish pop king teamed up with Cuban acts Descemer Bueno and Gente de Zona, and together they invited the world to dance alongside them in “Bailando.” The song, with its flamenco guitar accents, ended up to be one of the buzziest fusions in Latin music at the time — and the trio later clinched the Song of the Year at the 2014 Latin Grammy Awards. —L.V

95. Kali Uchis feat. Jowell & Randy | ‘Te Pongo Mal (Prendelo)’ 2020

Kali Uchis enlisted reggaeton veterans Jowell & Randy for one of the most surprising tracks on her stunning 2020 album, Sin Miedo (del Amor y Otros Demonios). Listeners had already heard her slippery voice gliding over reggaeton beats on “Nuestro Planeta,” from 2018’s Isolation, but on “Te Pongo Mal (Prendelo),” she fully embodies reggaeton-era pioneers like Ivy Queen as she empowers herself and asserts her sexuality. Her voice, sultry and confident, fits right in with Jowell & Randy as they give the track an energetic boost. —M.M.

94. Tainy feat. Julieta Venegas and Bad Bunny |’Lo Siento BB :/’ 2021

Tainy’s limitless vision for reggaeton has always been experimental and futuristic, and “Lo Siento BB:/” was one of the best examples of all the influences and references that live inside his head. Released in 2021, the song opened with early-aughts indie darling Julieta Venegas singing over an otherworldly piano — an unexpected and inspired choice that fit right into the dreamy production. The second surprise came after: Her voice was joined by Bad Bunny’s hilarious, heartsore verses, shaping a moment that was endearing and exciting. —L.V.  

93. Danny Ocean | ‘Me Rehúso’ 2016

Some might not consider this Venezuelan singer-songwriter a proper reggaetonero, as his choice of rhythms tend to swing beyond the confines of the foundational dembow riddim. Yet his breakthrough 2016 single encapsulates the genre’s most romantic inclinations perfectly over its polyrhythmic base. As Ocean pleads with a lover at the likely end of a relationship, one can’t help but get caught up in it all. —G.S.

92. Don Miguelo | ‘Como Yo Le Doy’ 2013

Don Miguelo’s first hit in the mid-2000s was “Que Tu Quieres,” and his stunning follow-up was a David-and-Goliath story of epic proportions. When he’d finished “Como Yo Le Doy,” few people believed in the track, which came at a time when media had declared reggaeton dead. But the Dominican artist broke through triumphantly, becoming a mainstream star. It also spun off two buzzy remixes, including one with Pitbull and another with J Alvarez and Zion. —J.M

91. Nicky Jam and J Balvin | ‘X’ 2018

Nicky Jam is one of reggaeton’s most enduring veterans, with a career spanning all the way back to 1995. He’s also had the remarkable ability to reinvent himself: After his momentum screeched to a halt in the early 2000s, he relaunched his music from Colombia, architecting the sound of Medellín in the process. “X” is a reflection of just how well things worked out. The reggae- and dancehall-infused collaboration with J Balvin was a viral hit that blasted up the charts everywhere. —M.M.

90. Rauw Alejandro an Chencho Corleone | ‘Desesperados’ 2021

Always a fan of old-school reggaeton, Rauw Alejandro turned to a special veteran for this upbeat track from his chromatic album Vice Versa: Seconds into the song, the instantly recognizable voice of Plan B’s Chencho Corleone braids into Rauw’s smooth singing, and the two of them trade audaciously sexual lyrics over a galloping dembow beat, haloed in an electronic glow. “Desesperados” went quadruple-platinum, successfully embodying both the genre’s past and present.  —L.V. 

89. Alex Gargolas feat. Randy | ‘Soy Una Gargola’ 2006

An underrated force, Alex Gargolas has left a mark on the genre with plenty of songs — especially “Soy Una Gargola.” In 2006, the Puerto Rican producer teamed up with Randy Ortiz to deliver this slinky, electronic-infused track that personified the nocturnal spirit of the club. As Ortiz sings about being a gargoyle-like creature of the night, his slick vocals emphasize the rich darkness of the production and bring out the freaky side of perreo. —L.V.

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Nio Garcia, J Balvin, and Bad Bunny

‘AM Remix’

2021

Nio Garcia was already having a breakthrough moment with the smooth romance of “AM,” and then his seismic remix amplified the song’s powers even more. He tapped J Balvin and Bad Bunny, which proved to be a brilliant move not just because of their renown in the industry, but because of how easily they slid over breezy production that had been refined by the late Flow La Movie. Together, they each brought out a softer, more sensual side of the genre. —L.V.  

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Shakira feat. Maluma

‘Chantaje’

2016

Following a brief fling with reggaeton influences on 2005’s “La Tortura,” Shakira slithered back to the genre with 2016’s “Chantaje.” This time, the Colombian pop diva was accompanied by one of her compatriots on the rise, Maluma. Backed by slinky beats with an electronic touch, courtesy of Medellín production mavericks the Rudeboyz, Shakira’s sensual delivery collided with Maluma’s flirty flow, resulting in a steamy collaboration and multiple Latin Grammy nominations. —L.V.

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 Angel y Khriz feat. Gocho “El Lápiz de Platino” and John Eric

‘Na De Na’

2008

“Na De Na” is immediately recognizable from the snaps at the beginning alone. The song, led by the kinetic duo Angel y Khriz, builds up to its first chorus, which features a beat drop that’s prime for any club setting and the easily screamable chant “Ella no suelta na’ na’ na’/Dice na’ na’ na’/Que no hay na’ na’ na.” It was a precursor to the boisterous anthemic club songs that would come in 2009, when people needed to let it all out on the dance floor. —M.M.

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 Becky G and Natti Natasha

‘Sin Pijama’

2018

Save for a few pioneers like Ivy Queen, the reggaeton space has been woefully male-dominated for years. Luckily, that’s starting to change, and one track that helped move the needle was 2018’s “Sin Pijama.” Becky G, who had been pivoting from upbeat English-language pop, enlisted Natti Natasha for the unapologetic, sexually empowered anthem. Though it saw some controversy, the two singers stood by it, with Natti saying at the time that women “want to see themselves portrayed in music as they really feel.” —M.M.

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Farruko

‘Pepas’

2021

Puerto Rican rapper Farruko built a long and successful career mainly doing reggaeton and trap, but he had his biggest hit by far with this inventive left turn: a sped-up nod to the EDM-hybrid sound guaracha, driven home by a huge shout-along chorus. The carefree, hard-partying spirit of “Pepas” hit the perfect note of optimism post-pandemic, and the song became a huge global smash. As Farruko told Rolling Stone, “It was a risk, but it worked.” —J.D.

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Wiso G

“El Domingo Por La Tarde”

2004

Hip hop and reggaeton have always been inextricably linked, and Nineties rap influences left a deep mark on the genre’s Puerto Rican artists in particular. Spitters like Wiso G embodied the best of rap en espanol as they let their impeccable flows unfurl over non-stop dembow loops in shows of stamina and skill. The early track “El Domingo Por La Tarde” was a hilarious, off-the-dome account of a day in the life of Wiso that showed how irresistible his delivery was, no matter what he was rapping about.  —J.L

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Randy and Ape Drums

’23’

2021

​​“23” was bound to become a viral hit. The master collaboration brought together Randy Ortiz, the king of perreo; taste-making DJ-producer Ape Drums; and and wordsmith and freestyle champion Yartzi “El Cacique,” who each helped shape an indisputable perreo blockbuster for modern times. With an iconic sample of Young Gunz’ 2003 “Can’t Stop, Won’t Stop” at the beginning, the track moves to a quake, offering a suitable background for proper ass-shaking that took over clubs and TikTok alike. —J.M.

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Anitta

‘Envolver’

2022

Anitta’s global success reached critical mass this year with “Envolver,” the viral hit from her 2021 album, Versions of Me. The Brazilian superstar tapped Bad Bunny’s frequent collaborators Súbelo NEO to produce the reggaeton romp, which is driven by unabashedly provocative lyrics about taking control. The reaction was next level: Fans jumped on the “Envolver” dance challenge on TikTok and helped shoot the track to Number One on Spotify’s Global charts, landing her a Guinness World Record as the first solo Latin act to reach that peak. —L.V.  

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Baby Rasta and Gringo

‘La Competencia’

1997

In the Nineties, rappers Baby Rasta and Gringo laid the groundwork for reggaeton by lighting up marquesina parties and underground clubs in Puerto Rico with their hard-hitting, rabble-rousing style. The duo, associated with the collective the Noise, weren’t afraid to get confrontational, and that bellicose energy is all over their OG anthem “La Competencia.” Baby Rasta’s melodic tenor offsets Gringo’s gruff, aggressive bars as they race over dembow riddims and flashes of hip-hop beats in a bold song that seemed to predict reggaeton’s potential for exciting genre fusions. —L.V.

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Wisin & Yandel

‘Sexy Movimiento’

2007

The sounds used in reggaeton often mirrored those used in electronic dance genres—the simple result of artists mining whatever was available on Fruity Loops and easily accessible production computer programs. That explained a particular moment when the genre went techno and produced hits such as “Sexy Movimiento” from Wisin & Yandel’s 2007 Los ExtraTerrestres. Distorted voices, wild synths, and intergalactic flourishes joined themes of sexy moves, sexy bodies, and sexy women, announcing to the world that rave perreo was in full effect. —V.B.

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Becky G and Bad Bunny

‘Mayores’

2017

Although Becky G had been making music since 2012, she found her sound through reggaeton and Latin pop — and “Mayores” showed her landing on her own style. Suggestive lyrics about wanting to be with more, ahem, mature men was risqué for the “Shower” singer, but she was able to blend her pop tendencies with the sensual underpinnings of reggaeton. A feature from a then-rising Bad Bunny, who playfully suggests she should go for younger guys, was the touch of danger needed to nail its grown-and-sexy vibe. —M.M.

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Latin Fresh

‘Ella Se Arrebata’

1996

“Ella Se Arrebata” needs to be celebrated as reggaeton music in one of its earliest forms. With strong dancehall and reggae influences running through the beat, the Panamanian singer showed off his kinetic flow, which brought in elements of rap and hip-hop, while serenading the women who caught his attention on the dance floor. The track is a brilliant call-back to the genre’s roots in Panama and the MCs whose flows continue to inspire artists today. —L.V.

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De La Ghetto feat. Randy

‘Sensacion Del Bloque’

2007

After years performing as a duo with Arcángel, De La Ghetto propped up his solo career and began experimenting with everything he could, casting a wide net across all his influences. He proved himself a versatile talent who could flit between hard-hitting trap and party reggaeton, but “Sensacion Del Bloque” was a softer entry into his catalog, constructed on piano riffs, a catchy beat, and silky vocals that were right at home with the English-language R&B scene at the time. —V.B.

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Karol G and J Balvin featuring Nicky Jam

‘Mi Cama (Remix)’

2018

Throughout her career, Karol G has shown she refuses to stay static. The Colombian artist keeps evolving, with blockbuster bangers that push beyond the genre and land in surprising sonic territory. One of the early tracks that showed her versatility was “Mi Cama,” an upbeat, empowered hit that inspired a remix with J Balvin and Nicky Jam. She sidled right up to guys and held her own, letting the world know she was a star in the making.—J.L.

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Sech

‘911’

2021

Sech’s “911” is the breakup song every adult has been craving: It’s deliciously petty, hysterically funny, and incredibly emotionally intelligent, reflecting the best of pop culture’s “sad boy” era. Lines such as “Tú no eres mala, tú eres maldición” are more lacerating rendered through Sech’s syrupy voice, and though the lyrics are a little cruder than Panama’s typical romantic style, “911” lands as one of the most versatile, layered heartbreak tracks in the genre’s recent history.—K.E.

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Natti Natasha

‘Me Gusta’

2018

Collaborating with the likes of Bad Bunny, Becky G, and Ozuna raised this Dominican artist’s profile considerably in the mid-to-late 2010s. Though firmly established as a star in her own right by that decade’s end, she still had to show and prove ahead of her major-label debut, IlumiNATTI. The simmering hit “Me Gusta” benefitted from its otherworldly atmospheres and promise of forbidden kisses. —G.S.

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Héctor y Tito feat. Don Omar & Glory

‘Baila Moreno’

2004

Before Héctor turned to religion and Tito went solo, the Puerto Rican duo were setting parties ablaze with their raucous energy. For “Baila Morena,” the two called in reinforcements: Don Omar and Glory, some of the most hard-hitting acts in the game, joined them while they threw down over an aggressive dembow beat, fired up with the sound of AK-like gunfire. Together, they turned out a hit that lit the airwaves, or as they put in the lyrics, “a fuegote.” —L.V.

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Speedy

‘Amor Con La Ropa’

2000

Speedy’s idiosyncratic, somewhat nasally voice had a magnetic-like quality that made fans flock to him during reggaeton’s budding days. To hear the appeal, you just have to hear him lose it on the ominous groove of “Amor Con La Ropa,” an old-school banger that gets completely turned on its head when the beat speeds up out of nowhere. Speedy erupts into a vowel-led freestyle that adds the necessary fireworks to the legendary track. —J.L.  

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Rosalia and Ozuna

‘Yo X Ti, Tu X Mi’

2019

The title translates to “Me for You, You for Me,” and that’s definitely the vibe on this Latin Grammy-winning cross-Atlantic collaboration. Everything about this tune exudes warm, playful generosity, from the way the track gracefully brings together R&B, reggaeton, tropical house and flamenco, to the flirty chemistry Rosalia and Ozuna enjoy as they trade verses. It’s a reggaeton track that feels downright pastorale in its bright, easeful elegance, like finding an open, airy park to hangout in the midst of a bustling city.—J.D.

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Notch and Baby Ranks

‘Verme’

2006

“Verme” felt like a sonic snapshot of the twinkling, sun-lit beauty of the Caribbean. The Puerto Rican and Dominican singer Baby Ranks teamed up with Jamaican American artist Notch, who brought an R&B vibe to their feel-good collaboration. Production duo Luny Tunes blended reggaeton with elements of ragga soca music, offering a refreshing moment in the genre as both artists sang breezily about moving on from their exes with punchy lyrics in English and Spanish. —L.V.

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Frankie Boy

‘Liza Love’

2000

With his breezy delivery and knack for freestyling, Frankie Boy was a regular fixture on underground mixtapes in the early days of the genre. Songs like the skittering Playero favorite “Liza Love” captured the way DJs at the time would keep the beat going as long as they could, leaving it to the most talented MCs to improvise and introduce new dynamics to the track. Frankie Boy was among the best, hooking himself into anything that got thrown his way and setting a standard for reggaeton’s future rappers. —J.L. 

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Don Omar feat. Lucenzo

‘Danza Kuduro’

2010

Based on a style of dancing and music that originated in Angola, this infectious chart-topper from Puerto Rican artist Don Omar and Portuguese-French singer Lucenzo rides along on a galloping hand-clap beat and a melody that blurs a synth and an accordion, feeling at once modern and traditional. The tune’s joyous sense of release was hard-won: The kudoro dance style developed in Angola as a good-time means of uniting a society that had experienced decades of civil war. —J.D.

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Daddy Yankee feat. Bad Bunny, Natti Natasha, and Becky

‘Dura (Remix)’

2018

Daddy Yankee has always come through with music that keeps his fans moving. In 2018, almost as though he was predicting the rise of TikTok, the Puerto Rican icon inspired a number of dance challenges with his colorful hit “Dura.” A magnetic remix, featuring Natti Natasha, Becky G, and Bad Bunny, emphasized the song’s buoyant dembow beats, with each artist taking a moment to drop a bright, beaming verse that quickly made the track one of the biggest hits that summer. —L.V.

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Becky G and Karol G

‘Mamiii’

2022

In a genre still largely dominated by men, Becky G and Karol G seized the spotlight with a gigantic, female-empowered anthem that showed why they’re some of the genre’s leading ladies. As soon as Becky G heard the track, produced by Ovy On The Drums with a co-writing credit from rising artist Elena Rose, she added a few gritos and guitars and brought it to Karol G. The final result captures the best of their personalities — sweet and brazen — with belt-ready verses and punch lines celebrating self-reliance and independence. —E.L.C.

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Héctor El Father

‘Dejale Caer To’ El Peso’

2005

Héctor El Father has tons of bangers that still hit, which is no small feat considering he has been out of the game for years following a religious conversion. He was possibly at his best here with a secret weapon: the rapper Yomo. Thumping kicks and dramatic strings on the production set the stage for Yomo as he delivers one of the best malianteo romántico lines in the genre: “pa’ los enemigos plomo y pa’ las gatas besos.”—V.B.

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Aventura Feat. Don Omar

‘Ella Y Yo”‘

2005

Bachata renegades Aventura and reggaeton maverick Don Omar have had one thing in common throughout their lengthy careers: They’ve never done what people have expected. “Ella Y Yo” was one moment no one saw coming, where both acts mixed the best of their respective genres and served up a masterclass in lyricism, storytelling, and bachaton. The song unfolds like a back-and-forth conversation between two men at a bar and Don Omar slowly reveals that he’s been with Romeo Santos’ woman, the drama and tension rising alongside the production. —J.L.

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Ozuna

‘Dile Que Tú Me Quieres’

2017

Ozuna’s silky soprano has become a pop mainstay, but his finest solo track is this supple, smooth highlight from his excellent 2017 LP, Odisea. Over a plush keyboard melody and an easefully body-moving reggaeton groove, the singer delivers a vaultingly heroic romantic entreaty, stretching syllables to the sky in a striking showcase for his athletic natural talent. In a world that too often equates hardness with realness, the openhearted buoyancy of his performance is reassuringly old-school in the best way. —J.D.

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Maluma

‘“Hawái”

2020

​​“Hawái” avoided the pitfalls of clichéd reggaeton and enamored millions with its potent, infectiously catchy chorus, sticky and melodic enough to be one of the greatest songs in the genre. Released as part of Maluma’s 2020 album, Papi Juancho, the Colombian singer luxuriates in the best of Medellín’s silky sound while laying out the intricacies of love in times of social media. Maluma knew he’d struck something special: In 2021, he described “Hawái” to Rolling Stone as “the biggest song of my career.” —R.D.

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Trebol Clan, Joan and Héctor El Father

‘”Gata Fiera’

2004

Dominican production duo Luny Tunes sprinkled “Gata Fiera ” with their signature bachata guitars as the song lays out the story of a woman who leaves a trail of broken hearts wherever she goes. Brilliantly centered on the push and pull of male and female vocalists, the narrative-driven track features Trebol Clan, Joan, and Héctor El Father, who split their time claiming they won’t be the next victims of a dangerous love game. —V.B.

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La Factoría feat. Eddy Lover

‘Perdóname’

2006

The Panamanian group La Factoría, which included reggaeton luminary Demphra and Joysi Love, often embodied female strength and power — yet their memorable smash “Perdóname” remains one of the most respected and unabashedly sentimental reggaeton ballads ever written. From the very first line, featured artist Eddy Lover sings in a falsetto so gentle that it sends listeners soaring into their feelings. And though the song pulled from the most emotional strains of R&B, the track never loses its momentum, thanks to rapid-fire verses from La Factoría’s powerhouse women. —J.L.

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 Tonny Tun Tun, Daddy Yankee, Luny Tunes, Héctor el Father, Wisin & Yandel

‘Noche De Entierro’

2006

By the time this song appeared on Luny Tunes and Tainy’s Mas Flow: Los Benjamins, reggaeton was a worldwide phenomenon. The production tips its hat toward that global success, incorporating instrumentation from the Andes to the Caribbean in a kind of pan-Latin solidarity: Opening with dramatic strings and drum rolls, the track switches into an unexpected pan flute melody and reveals a vallenato-like accordion. Daddy Yankee steals the show on a star-studded cast of vocalists, Daddy Yanke, though Héctor El Father gives him a run for his money. —V.B. 

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J Balvin and Bad Bunny

‘La Canción’

2019

When Oasis dropped, that monumental pairing of two of contemporary reggaeton’s superstars shook the Latin-music world. It followed two tremendous solo efforts from the artists, Vibras and X100PRE, respectively, and yielded this slow-burning single. With its muted thump, plaintive keys, and street-corner jazz accents, “La Canción” finds both artists sharing a wistful moment over a former lover conjured by hearing a certain song. —G.S.

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The Noise feat. Ivy Queen

‘Al Escuchar Mi Coro’

1997

There is truly nothing like La Caballota on the Noise’s early tapes, all braggadocio and raw force. This 1997 song off The Noise 7 mixtape references “Muchos Quieren Tumbarme” from her past repertoire, which despite having come out only a few years earlier, was already becoming a deeply ingrained classic. The grit in Ivy Queen’s voice gives way to the deep timbre that established her as a heavy-hitter and shows off the authority that her fans have come to know and love. —V.B.

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Plan B

‘Candy’

2014

While explicit songs about sexy women can easily tip into sexual objectification, “Candy” expressed something closer to reverence for women who love sex and refuse to be pinned down. From Plan B’s 2014 album, Love And Sex, “Candy” put a spotlight on women who make pleasure their main pursuit, to Chencho and Maldy’s great admiration and bewilderment — and to the delight of listeners who continue blasting the track, which is name-checked and referenced across reggaeton even today. —V.B.

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Tony Dize feat. Yandel

‘Permitame’

2008

“Permitame” felt like a projection of the flexibility and range reggaeton lovers had — and continue to have — for a wide range of sounds. The electronic-dance track was produced by a young Tainy, who actually gets a shoutout on the song for being an all-time great at the tender age of 16 (“Que a los dieciséis año’ anda en Mercede”), and features Yandel and Tony Dize on the beat, wooing girls at the club and taking dance floors by storm. —V.B.

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Rosalía and J Balvin feat. El Guincho

‘Con Altura’

2019

When J Balvin joined Rosalía on “Con Altura,” the Spanish singer was coming off the critical acclaim of her experimental second album, El Mal Querer, heavily rooted in flamenco traditions. On this mega-collaboration, she mixed her signature style with Balvin’s verses, El Guincho’s production, and Caribbean influences that ranged from Playero mixtapes to an audio sample of Dominican artist Mariachi Budda, who coined the phrase “con altura.” The final result was an ubiquitous flamencotón hit that propelled Rosalía to new audiences and scored a Latin Grammy. —M.M.

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Arcángel

‘Pa Que La Pases Bien’

2008

“Pa’ Que La Pases Bien” is an example of what happens when an artist proves the industry wrong. At a time when many label insiders were convinced reggaeton had stalled, Arcángel freshened things up with a little perreo-galactico, a slightly cosmic, electro-tinged take on the genre. Production from Luny Tunes cleverly fused hyper-techno and trance with Caribbean instrumentation, and the final result became a trippy favorite played in mainstream clubs and basement parties alike. —K.E.

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Jowell & Randy feat. De La Ghetto

‘Un Poco Loca’

2007

“Un Poco Loca” benefits from Jowell & Randy’s long-standing connection and a clutch sample of Chaka Demus & Pliers’ “Murder She Wrote.” The back-and-forth between the duo is seamless, but the interplay is made more impressive with the addition of De La Ghetto, the reggaetonero who was making a solo name for himself at the time after years on the road with Arcángel. By the end of the song, they’ve lived up to the “musical massacre” they refer to in the lyrics. —E.L.C.

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Glory

‘Perreo 101’

2005

Class will forever be in session as Glou/Glory teaches her students a thing or two about pleasure in this sexy how-to anthem by one of the foremost Black female icons of perreo. A lasting social commentary on dominance and submission, ”Perreo 101” pushed boundaries when it was released in 2005 as part of the rapper’s album Glory, standing out for being a fun and seductive hit that makes a statement in the presence of the genre’s male-driven power dynamics. —K.E.

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DJ Nelson, Ñejo, and Tego Calderón

‘No Quiere Novio (Remix)’

2006

This gem sparkles even in a genre full of soltera anthems. DJ Nelson hammers out production so unusual, it sounds like reggaeton in outer space. Meanwhile, Ñejo and Tego’s sick flow is delivered with such ease that it’s only once the listener tries to sing along that they realize how deceptively difficult the song’s verses are. The track feels like a paean for all the fiercely independent women who hate the intrusive and ever-present question, “Y el novio?” —V.B. 

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Alexis & Fido

‘5 Letras’

2007

Many reggaeton duos split up after achieving fame, but Alexis & Fido have always multiplied their powers together. The two of them grew up in Puerto Rico and saw major success after their 2005 breakout single, “Eso Ehh!!” In 2007, they followed things up with “5 Letras,” a song built on dramatic samples, arhythmic sonic patterns, and futuristic synths that channeled sounds emerging in the hip-hop space while foreshadowing just how experimental reggaeton could — and would — get on later hits. —M.M.

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Tego Calderón feat. Voltio

‘Güasa Güasa”’

2002

This track served to establish Tego Calderón as a cutthroat lyricist; over four minutes, the Puerto Rican legend spits with ease in what feels like a breathless freestyle. Infused with the island’s colloquial slang, “Güasa Güasa” knows its power. “My lyrics make them feel small,” he raps, roughly translated. Alongside his frequent collaborator Voltio, Calderon goes after his adversaries here, amounting them to nothing but posers. The song stands as a reminder of the genre’s savage roots and a prime example of its proud street/calle reggaeton origins. —E.L.C.

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Alberto Stylee and DJ Nelson

‘Vengo Acabando’

1997

Leveraging a sharp interpolation of Annie Lennox’s “Sweet Dreams,” genre OGs Alberto Stylee and DJ Nelson turned out a crisp hit that was a little ominous — and well ahead of its time. The track predicted an electro-surge that erupted in the 2020s, when reggaetoneros began experimenting more wildly with electronic dance music elements. Doing this in the mixtape era put the twosome at the vanguard of the genre and gave us an early peek at all the places reggaeton would go. —V.B.

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Lorna

‘“Papi Chulo… Te Traigo El Mmmm’

2003

A powerful and sexy ode to all that women bring to the table, Lorna’s “Papi Chulo” will forever live at the center of raunchy reggaeton parties. The Panamanian rapper, known for her distinctive voice, was just 19 when she recorded the track after deciding she wanted to pursue music. Her debut single took off in multiple countries, inspiring confidence, emboldening women to flaunt what they have, and encouraging them to assert themselves always. —K.E.

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Don Chezina

‘Tra Tra Tra’

1998

Building an entire track off one word is impressive; making it a genre classic is a complete feat that Puerto Rican rapper Don Chezina achieved effortlessly. Known for his electric, rapid-fire delivery, the early genre pioneer had a singular, slightly nasally tenor that practically leapt off mixtapes — and made it no surprise that his chants of “tra” shot him from the underground to global stages. The late-Nineties hit hasn’t lost any of its staying power: It’s constantly sampled and shouted out on reggaeton songs today. —J.L.

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Luis Fonsi feat. Daddy Yankee

‘Despacito’

2017

“Despacito” didn’t just break barriers in reggaeton; it changed the rules for the Latin industry in general. The viral super-smash spent more than 55 weeks at the top of the Billboard charts, reaching global heights unprecedented for a Spanish-language track and making history as one of the most streamed songs ever. Certainly, such success and ubiquity had its drawbacks — “Despacito” became virtually inescapable for a while, eclipsing a variety of diverse Latin sounds — but it still opened the floodgates for a new era in Spanish-language pop. —R.D.

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Natti Natasha and Ozuna

‘Criminal’

2017

Lighthearted and endearing, “Criminal” made a case for putting the reggae back in reggaeton when it premiered in 2017. The slow-grinding ballad, produced by Haze, is built on savvy wordplay and throwback dancehall riddims that provide a gorgeous backdrop for Natti Natasha and Ozuna to shine seductively. In addition to being a chart-topper across Latin America, the video for the track became a super-smash that quickly garnered more than 1 billion views.—K.E.

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Tego Calderón

‘Métele Sazón’

2003

Calderón’s easy and impeccable flow was on full display on this Mas Flow tape cut from 2003. Dedicated to “shorties en lo’ New Yore’” and “pa’ lo’ maleante’ en la’ prisione” (“the shorties in New York” and “the gangsters in prisons”), “Métele Sazón” featured Luny Tunes distinctive bachata guitar, giving the song a Dominican touch. Tego’s inimitable style throughout his catalog emanates from a deep knowledge of who he is, and “Métele Sazón” is braggadocio at its best, fully backed up by his skillset. —V.B

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Alexis & Fido feat. Baby Ranks

‘El Tiburón’

2005

Early associates of Wisin & Yandel before they were Wisin & Yandel, this Puerto Rican duo broke out in 2005 sporting the monikers (and album titles) Los Pitbulls and Los Reyes del Perreo. Among their early hits was “El Tiburón,” featured prominently on production team Luny Tunes’ classic compilation Mas Flow 2. Joined by Baby Ranks, they deliver an anthem focused specifically on the sweatiest of dance floors. —G.S.

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La Sista feat. Divino

‘Destino Cruel’

2007

The xylophone-laced melodies that open “Destino Cruel” are nostalgic and evocative, setting the tone for Maidel “La Sista” Canales, a native of Loiza, as she sings about lingering memories she can’t forget: “No se si fue el dulce aroma de su piel que me cativo,” she croons. Her voice is delicately paired with Divino, who harmonizes with her over a heavy bass line for sentimental romantiqueo that reflects the R&B influences at the time. —J.M.

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Tito “El Bambino” feat. Randy

‘Siente El Boom’

2011

After getting recognition as part of the duo Héctor & Tito, Tito el Bambino branched off on his own and came up with this mammoth, aptly named hit. The song rattled dance floors when it came out, thanks to a kick-drum heavy beat that propels the production forward. All the while, Tito and Randy trade off verses about how they attract all the women with their magnetic sound. —M.M.

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Yaga & Mackie feat. Arcángel and De La Ghetto

‘Aparentemente’

2007

Hip-hop arguably occupies as much space in reggaeton’s core as dancehall does, a product of the genre’s formative years and aesthetic. A quick glance at the cover of Yaga & Mackie’s 2007 album, La Reunión, might lead one to think they were rappers, and the Bad Boy-type-beat hybrid behind this iconic single with Arcángel and De La Ghetto speaks to that. —G.S

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Ivy Queen

‘Te He Querido, Te Llorado’

2012

The reggaeton matriarch built her success on yoking her deep, commanding voice to hard-hitting tracks designed to detonate a dance floor, but on this 2005 hit, she switched things up a bit, mixing reggaeton and bachata for a more-restrained sound that offered a more-nuanced performance. But “Te He Querido, Te Llorado” was anything but soft; Ivy Queen, who had just gone through a breakup, sings about lashing out on a cheating lover in specific, unsparing terms, giving the song a powerful element of personal catharsis. —J.D.

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J Balvin feat. Farruko

‘6 AM’

2013

Back in 2013, J Balvin was a little-known Colombian artist who hadn’t made waves across the globe — yet. That all changed when he teamed up with Puerto Rican rapper Farruko for the breakthrough single, “6 AM.” Pretty soon, there wasn’t a speaker at a backyard barbecue that wasn’t blasting the track, which was a perfect combination of upbeat reggaeton and sunshine-bright production. In addition to becoming a giant summertime hit, it put Balvin on the map and set him up for his worldwide expedition. —M.M.

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Voltio feat. Residente Calle 13

‘Chulin Culin Chunfly’

2005

For this ridiculously rowdy club banger, Voltio teamed up with Calle 13’s Residente, a collaboration that brought out their shared sense of humor and playful irreverence. United over a menacing beat, the two of them traded raunchy verses comparing sex to a smorgasbord of foods. The contrasts made the song work: Voltio’s tough edge was rounded out by Residente’s smart-alecky, slightly taunting flow, and their joint refrain of “ojalai, ojalai” was instantly memorable. —L.V.

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Nicky Jam feat. Daddy Yankee

‘En La Cama’

2001

Before he was one of the biggest stars in the business, Nicky Jam was a teen prodigy who got everyone talking with his precocious sense of rhythm and rhyme. He even caught Daddy Yankee’s attention, and pretty soon, the future reggaeton titans had joined forces for “En La Cama,” a track that leveraged their hyper-fast flows over a full-throttle beat. They mastered the art of collaboration and gave people another hit from Los Cangris, the superduo they formed that remains one of the greatest pairings in reggaeton history. —L.V.

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Don Omar

‘Pobre Diabla’

2003

“Pobre Diabla” came out almost 20 years ago, yet it still remains one of the most memorable songs in Don Omar’s repertoire — and in reggaeton in general. As he employs rich guitars he’s been drawn to throughout his career, Omar sympathizes with a woman who hasn’t been treated right by her partner, sending an uplifting message and providing a soft side to his discography. —M.M.

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Rakim & Ken-Y

‘Down’

2006

Millennials might remember belting out the lyrics to this Rakim y Ken-Y classic as teens, even if they’d never lived through heartbroken anguish at the center of the lyrics. Released as the first single of Rakim & Ken-Y’s debut album, MasterPiece, in 2006, “Down” shot the Puerto Rican duo to the top of the charts and offered a blueprint for emo reggaeton, custom-made for lovers with their hearts on their sleeve. —E.L.C.

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Tego Calderón

‘Dominicana’

2003

One of the most impressive things about “Dominicana” is its minimalism: Light percussion, the shadow of a cowbell, and a piano element form the beat as Tego Calderón proclaims what he loves most about Dominican women. His unique style fuses multiple genres, such as salsa, dancehall, and hip-hop, indicative of the eclecticism that made him such a towering figure in the early 2000s. An anthem that extolled the beauty of Caribbean women was a welcome breath of fresh air when it came out in 2003 — and continues to be today. —M.M.

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Héctor El Father feat. Wisin & Yandel

‘El Teléfono’

2006

The collaborative album Los Vaqueros was Wisin & Yandel’s first project under their label WY Records, and “El Teléfono,” featuring Héctor El Father, immediately stood out on the collection. Produced by a then-17-year-old Tainy, the song shines with its sharp-witted approaches, including the recognizable telephone dial that welcomes the beat drop and a heaving bass that provides just the right setting for Hector to launch into electrifying verses.—J.M.

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Daddy Yankee

‘Rompe’

2005

Following the massive success of Barrio Fino and its sensational singles, Daddy Yankee struck perreo gold (actually, RIAA Platinum) with this Monserrate- and DJ Urb-produced banger. Its message was all but designed for the clubs, with boasts and come-ons appropriate for the bleepy thump of the beat. A remix arrived with G-Unit soldiers Lloyd Banks and Young Buck at the height of their commercial powers, a win for all involved. —G.S.

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Plan B

‘Si No Le Contesto’

2010

After an eight-year hiatus, Chencho Corleone and Maldy of the duo Plan B released the jam-packed 2010 album House of Pleasure, featuring the futuristic-sounding “Si No Le Contesto.” The song is crisp and polished, incorporating background synths that could easily fit into the scene today. Their forward-looking approach made Plan B an inspiration to younger artists: They’ve been name-checked on Rosalía’s “Candy,” and Chencho has been tapped for Bad Bunny’s “Me Porto Bonito” and Rauw Alejandro’s “Desesperados.” —M.M.

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 Don Omar feat. N.O.R.E., Fat Joe, and LDA

‘Reggaeton Latino’

2005

In the early 2000s, Latinos in the U.S. hip-hop scene couldn’t ignore what was happening in Puerto Rico. Not only did they acknowledge the talent bursting out of the island, they wanted to be part of it all. That desire for cross-cultural connections saw Don Omar team up with N.O.R.E., Fat Joe, and LDA on the triumphant “Reggaeton Latino,” part of a compilation released by producer Boy Wonder. Helmed by Don Omar’s noteworthy baritone, the song became a hit, spending 44 weeks on the Billboard charts.

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Glory

‘Erotica Danza’

1999

Despite singing on some of the most globally recognizable hooks of reggaeton, Glory has not gotten the credit she deserves for taking genre favorites to the next level. And though her work on these is excellent, it’s her solo work where she truly shines. With its relentless beat, the classic “Erótica Danza” from the beloved Playero tapes — 1999’s Playero 41 to be exact — unveil Glory’s charisma to the fullest and reveal the impressive scale of her talent. —V.B. 

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Wisin & Yandel feat. Romeo Santos

‘Noche De Sexo’

2005

One of the most alluring aspects of the band Aventura has to be Romeo Santos’ fluttering falsetto, so air-light and recognizable that it’s reminiscent of the Bee Gees’ Barry Gibb. It’s that vocal technique that adds so much sex appeal to the Wisin & Yandel classic “Noche de Sexo”: As the famed Puerto Rican duo launch into hard-hitting verses, Santos fully seduces listeners, singing, “Lay on my bed and prepare for sex.” —M.M.

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Casa De Leones

‘No Te Veo’

2007

Casa de Leones was a short-lived supergroup, but their biggest hit was enough to leave a huge mark in reggaeton. The members, who included Miguel A. De Jesús, Jaime Borge, Charlie Carlson, Héctor Padilla, and Randy Ortiz and Joel Muñoz of the long-standing duo Jowell & Randy, came together and quickly took over the charts with “No Te Veo.” It was a hit that showed off their musical chops with its instantly hooky chorus and calypso-inspired arrangements. —M.M.

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El General

‘Tu Pum Pum’

1991

Though “Tu Pum Pum” technically predated reggaeton, it helped bridge the necessary pieces as the genre bloomed from Panama to New York to Puerto Rico. Along with hip hop, Spanish language dancehall tracks like “Tu Pum Pum” traveled to the island through the come and go of the diaspora, creating the conditions for a global phenomenon. The Panamanian pioneer helped kick things off with a Spanish-language cover of Little Lenny’s dancehall hit “Punnaney Tegereg” that boosted him to stardom and laid an important foundation.—V.B. 

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J Balvin and Willy William feat. Beyoncé

‘Mi Gente (Remix)’

2017

J Balvin wasn’t lying when he sang, “El mundo es grande, pero lo tengo en mis manos.” He and producers Jean Rodriguez and Willy William really did have the world in the palm of their hands with the hit “Mi Gente,” which opens with an iconic vocal chop that serves as the track’s unrelenting heartbeat. Just when it seemed the power anthem couldn’t get bigger, a remix brought in Beyoncé, who fired off her verses in flawless Spanish. —J.M.

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Sech, Ozuna, and Anuel AA feat. Darrell & Nicky Jam

‘Otro Trago (Remix),’

2019

The original version of “Otro Trago” — which featured Latin trap favorite Darrell — made Sech a Panamanian talent impossible to ignore. Three months later, the remix solidified his space among heavyweights: Trap standout Anuel AA, reggaeton titan Nicky Jam, and honey-voiced artist Ozuna joined the nearly five-minute track, which gave each artist plenty of time to show off their skills and remind people that Puerto Rican and Panamanian MCs are the backbone — and pioneers — of the genre. —E.L.C.

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Calle 13

‘Atrévete-Te-Te’

2005

With such an expansive, left-of-center sound, Calle 13 always elided labels: Were they hip-hop? Were they reggaeton? When the brother duo, made up of rapper René “Residente” Pérez Joglar and Eduardo “Visitante” Cabra, released the impish hit, the strong cumbia rhythm, clever wordplay, and elaborate instrumentation didn’t exactly clear up any questions — but it did establish them as rebels who would always find a way to upend expectations and speak their minds about politics and the music industry. —R.D.

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Karol G feat. Nicki Minaj

‘Tusa’

2019

This one was undoubtedly for the girls. “Tusa,” Colombian slang for heartbreak, seesawed between acknowledging grief and delighting in self-love. Co-written and produced by Ovy on the Drums, who helped shape Karol’s soulful approach, the song was the Colombian star’s defining moment, establishing her as the genre’s passionate princess while taking her to global ascension. Nicki Minaj, no stranger to the urbano sphere, was the perfect addition, filling the track with iconic lines and ad-libs in Spanish. —E.L.C.

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Nando Boom

‘Ellos Benia (Dem Bow)’

1990

“Ellos Benia” remains one of the most foundational tracks in reggaeton’s history, representing the reggae en español movement in Panama that set the stage for reggaetoneros everywhere. When Nando Boom, the Panamanian rapper with a deep baritone and an immediately hooky flow, re-created Shabba Ranks’s “Dem Bow,” his engineers dropped in sharp, digital timbales and a few production flourishes that set a blueprint: From then on, reggaeton producers had a model for cutting up dancehall riddims into classic dembow loops that followed the genre through multiple generations. —J.L.

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Daddy Yankee

‘Lo Que Pasó, Pasó’

2004

Produced primarily by Eliel and Luny Tunes, 2004’s Barrio Fino was a veritable hit factory, yielding no fewer than five slam-dunk singles at a time when reggaeton was finally gaining greater global awareness. Following the sensational success of “Gasolina,” Yankee’s “Lo Que Pasó, Pasó” had a daunting task ahead of it. Thanks to its motivational message and salsa fusions, it became one of his signature songs. —G.S.

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Angel Y Khriz

‘Ven Bailalo’

2005

“Ven Bailalo” contains so much of what made the mid-2000s such a fertile period for the genre. Duos were dominant and prevalent at the time, and the tag team of Angel y Khriz did not disappoint with this bona fide reggaeton classic. Produced by Luny Tunes and Mr. G, it beckons listeners to the dance floor with rhumba elements and a thumping beat, not to mention the vocalists’ romanticizing of the Caribbean. —G.S.

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Bad Bunny, Nesi, and Ivy Queen

‘Yo Perreo Sola (Remix),’

2020

When Bad Bunny released “Yo Perreo Sola,” it was a distinctive and intentional reclamation of space for independent women — reminiscent of Ivy Queen’s “Quiero Bailar.” Though the original listed Bad Bunny as a solo performer despite Nesi’s voice echoing throughout the track, a blockbuster remix gives credit where it’s due: Released live at the 2020 Billboard Music Awards, the reworked version puts Nesi front and center and highlights Ivy Queen in what feels like a sign of respect from la nueva escuela. —E.L.C.

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Don Omar

‘Dale Don Dale’

2003

The first single from Don Omar’s debut album, The Last Don, “Dale Don Dale” foreshadowed the bounty of classics that the multi-hyphenate artist would release throughout his career. Assembled by Luny Tunes and Cheka, the beat consists of steel string guitar and soft synths. Between Omar’s brawny bars, you can hear a few lines — “Dale, papi, que estoy suelta como gabete ” — delivered by one of reggaeton’s most sensual, iconic voices: Glory “La Gata” Gangster. —J.M.

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Hector El Father

“Esta Noche De Travesura”

2004

A timeless anthem by one of the most prolific lyricists in all of reggaeton history, this infectious hit landed at many intersections when it came out in 2004. Sonically, it highlights the excellence of Caribbean sounds with its merengue and bachata fusions. Then there’s the innovative composition and celebration of biculturalism that give it even more layers, keeping it relevant and massively popular as reggaeton continues to grow at an outsize scale. —K.E.

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Plan B

‘Guatauba’

2002

Built on Chencho and Maldy’s unmistakable vocals and spare production by Blin Blin Music & Barbosa, this freaky cut from Plan B’s 2002 Guatauba XXX made the most of the Bam Bam riddim from Chaka Demus & Pliers massively popular “Murder She Wrote.” It also cemented the duo as artists who embraced racy provocations, knowing their risks would pay off. They were right: Though the song was considered pornographically explicit at its release, 20 years later, millions of people will casually hear “Guatauba” emanating from Balenciaga ads on IG. —V.B.

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Baby Ranks, Daddy Yankee, Tony Tun Tun, Wisin & Yandel, and Héctor El Father

‘Mayor Que Yo’

2005

“Mayor Que Yo” has seen many iterations over the years, but the best version brought together some of the biggest names in the business: Wisin & Yandel, Daddy Yankee, Baby Ranks, Héctor El Father, and Tony Tun Tun joined forces and sharpened one another’s skills, rapping over prominent bachata guitars and deep, brash reggaeton drums that enhanced each of their verses. A supernova of talent, the song continues to attract artists today: Natti Natasha recently tipped her hat to the seismic collaboration with “Mayor Que Usted.” —M.M.

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Casper Mágico, Nio García, Darell, Nicky Jam, Bad Bunny, and Ozuna

‘Te Bote (Remix)”

2018

The straightforward piano riffs on the “Te Bote” remix are simple, yet effective, marking a moment when reggaeton acts took the global stage as bona fide superstars. Specifically, the track helped launch a young Puerto Rican grocer named Bad Bunny into the pop stratosphere, highlighting the talent that was soaring out of Puerto Rico. The song also took on some political applications: During the 2018 midterm elections, Latinx voters made “Te Boté ” a de facto anthem in the dumping of Trump-supporting politicians. —V.B. 

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N.O.R.E. feat. Daddy Yankee, Nina Sky, Big Mato & Gem Star (2004)

‘Oye Mi Canto’

2004

As much as reggaeton gets framed as Puerto Rico’s story, the genre also boasts plentiful New York roots and branches. The city’s sizable boriqua population has played a vital role in music, from the days of boogaloo and Latin jazz through hip-hop’s epic come-up. Bilingual and brawny, “Oye Mi Canto” unites the diaspora with an elevating anthem that nodded to the late Big Pun amid a broader celebration of Latinidad. —G.S.

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Bad Bunny feat. Jowell & Randy and Ñengo Flow

‘Safaera’

2020

With a long and ongoing string of hits to El Conejo Malo’s credit, one could debate when exactly he transcended to superstar status. Even after massive chart successes like the Drake-assisted “MIA” and the star-studded “Te Boté,” there’s a strong case to make for “Safaera.” Bridging reggaeton’s past and present, with no less than Jowell & Randy by his side, Bad Bunny’s single storms through a variety of gratifying beat switches and epic vocal hooks. —G.S.

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Wisin & Yandel

‘Rakata’

2005

Seventeen years later and the word “Salte!” alone triggers a frenzy at a club. The sonic masterpiece, produced by Luny Tunes and Nely La Arma Secreta, blends a mix of spangling synths, while the onomatopoeic chorus of “Rakata! Rakata!” emphasizes the timbal sound at the center of the song’s classic dembow loop. The track embraced the very essence of reggaeton and added a sense of modernity right when the genre was reaching a mainstream fever pitch. —J.M.

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Zion y Lennox feat. Daddy Yankee

‘Yo Voy’

2004

Whether you call it sandungueo or perreo, the Carolina-based duo’s “Yo Voy” was primed to bring out the raunchiest and rawest from dancers. With Luny Tunes on the beat and the “Gasolina”-fueled Daddy Yankee in tow, Zion y Lennox scorched the clubs with their relentlessly thumping track. It endures to this day as one of the genre’s most beloved staples. —G.S.

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Don Omar

‘Dile’

2003

Well before becoming a recognizable Fast & Furious franchise fixture, El Rey was one of reggaeton’s biggest stars. Its title a nod to Mario Puzo’s renowned Mafia novel, The Last Don marked the genre’s commercial peak at the time. Produced by hitmaker Eliel with a notable sample of Colombian salsero Joe Arroyo, “Dile” serves up cocksure braggadocio as Omar gradually persuades his secret lover to dismiss her man. —G.S.

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Tego Calderón

‘Pa’ Que Retozen’

2003

Getting listeners to dance and then think was the career-changing advice that Tego Calderón’s father gave him. As a result, he created a perfect equilibrium on his debut album, El Abayarde, which celebrated Afro-Caribbean sounds while projecting social awareness. The DJ Joe-produced track “Pa’ Que Retozen” is most identifiable by guitar patterns found in bachata, making the song one of the first highly acclaimed “bachatón” classics and one that continues to inspire the genre. —J.M.

JOHN PARRA/WIREIMAGE2

Ivy Queen

‘Quiero Bailar’

2003

It’s hard to overstate the importance of “Quiero Bailar”: Undeniably the biggest feminist anthem in reggaeton history, the song was ahead of its time and profound beyond its creator’s years. Ivy Queen raised her voice, despite being outnumbered in a genre full of men, and told the collective story of women across the globe who wanted to celebrate their bodies and explore their sensuality while setting boundaries and empowering themselves on the dance floor. The message was a game changer, and one that continues to shift social paradigms in a culture mired by misogyny two decades later. —K.E.

RAY TAMARRA/GETTY IMAGES1

Daddy Yankee

‘Gasolina’

2004

By 2004, Daddy Yankee was already a proven talent in reggaeton’s underground scene, but he was busy preparing his next big move. He’d been planning an album — he wanted to call it Barrio Fino —that would set the standard in the genre, and he looked for inspiration wherever he went. A stroke of brilliance came unexpectedly: He was sitting at home, in his apartment in the housing projects of Villa Kennedy in San Juan, when he heard a man shout to a girl on the street: “Cómo le gusta la
gasolina!”

It was a funny, off-hand flirtation, a way of teasing girls who went after guys with fast cars in town, but Daddy Yankee heard magic. With his go-to producer Luny Tunes, he masterminded an explosive, revved-up hit that brought the genre to the rest of the world. The song shone a mega-watt light on what had been brewing in places like Panama and Puerto Rico, and officially announced that reggaeton was a global phenomenon here to stay. Decades later, it still holds up: The revered veteran launched a farewell tour this year after announcing his retirement from music, and in every stadium “Gasolina” is the legendary staple that gets legions of fans screaming loudest.–M.M.