The 70 Greatest Dylan Songs

14. Highway 61 Revisited
Highway 61 Revisited (1965)

“I always felt like I’d started on it, always had been on it, and could go anywhere from it,” Dylan said of Highway 61, which runs from his native Minnesota down to New Orleans. Here, he proved just how far he could take it. Recorded in a marathon session that also spawned ”˜Just Like Tom Thumb’s Blues,’ ”˜Ballad of a Thin Man’ and ”˜Queen Jane Approximately,’ the galloping title track from 1965’s electric breakthrough Highway 61 Revisited is Dylan in frizzed-out jeremiad mode. He leads a series of star-crossed characters (most famously, God and Abraham) down to America’s “blues highway,” while spitting venom at a series of American hypocrisies (phony patriotism, crass commercialism). Session musician Al Kooper claimed he lent Dylan the police whistle that jarringly kicks off and closes the song, instructing him to use it instead of his harmonica. “A little variety for your album,” he told Dylan at the time. “Suits the lyric better.”

15. Simple Twist of Fate
Blood on the Tracks (1975)

In ”˜Simple Twist of Fate,’ Dylan looks at an idyllic relationship that fell apart for reasons neither party can control. People logically assumed he was singing about the breakup of his marriage to Sara, but his lyric notebook for Blood on the Tracks reveals a different story. Originally, the song had a subtitle, ”˜4th Street Affair,’ named for the apartment at 161 W 4th St where he lived with girlfriend Suze Rotolo shortly after arriving in New York. The narrator of the song has moved on to meaningless one-night stands (as Dylan surely had in early 1975), but his heart was more than 10 years in the past.

16. Positively 4th Street
Bob Dylan’s Greatest Hits 1967
By Lucinda Williams

I love the theme of this song: jealousy over artistic success. I’ve seen it happen. “You see me on the street, you always act surprised/You say, ”˜How are you? Good luck!’ But you don’t mean it.” I discovered that when I tried to move back to Austin. I started there singing on the street in 1974, and then I tried to move back there later after I’d been in LA. It just didn’t work. Once we were playing somewhere, and I ran into a friend from back in the day, another musician. I was getting back on the bus, and she wanted to hang out ”“ she said, “Lucinda, sometimes I wish you weren’t famous.” What the hell is that supposed to mean? Jesus. But that’s what ”˜Positively 4th Street’ is about. I love that last line: “I wish that for just one time, you could stand inside my shoes/You’d know what a drag it is to see you.” It feels so good to sing it. I’ve heard that he wrote the song when he started getting famous and he was still living in the Village. Nobody wants to admit that that stuff goes on, and of course nobody knows what it’s like to be Bob Dylan. There’s only one of him. He’s so damn good at that.

17. This Wheel’s on Fire
The Basement Tapes (1975)

A kaleidoscopic evocation of chaos that can suggest anything from Vietnam to Dylan’s 1966 motorcycle crash, ”˜This Wheel’s on Fire’ is actually a song of lethal, disciplined fury. It is Dylan’s sneering promise ”“ in his original ’67 Basement Tapes vocal ”“ that the betrayal implied in the first two verses and made plain in the third (“You’re the one/That called on me to call on them/To get you your favours done”) will be avenged in full. Compressing that wrath into tight, mocking cadence must have exhausted him; Dylan asked the Band’s Rick Danko to come up with the melody, a slow and forlorn thing that also caught the despair of abandonment. “I was teaching myself to play piano,” Danko recalled. “Some music I had written just seemed to fit with Dylan’s lyrics.” ”˜This Wheel’s on Fire’ got a shot of adrenaline and a funky keyboard part (played on a repurposed telegraph key) when the Band recorded it for their 1968 debut album, Music From Big Pink. But the Byrds cut the definitive cover for their 1969 LP, Dr. Byrds and Mr. Hyde: Clarence White’s searing fuzz guitar sounds like apocalypse arrived.

18. Ballad of a Thin Man
Highway 61 Revisited (1965)

Dylan has written a lot of mean-spirited songs, but few are funnier or more cutting than this stomping tune about a dude who totally doesn’t get it ”“ or even what there is to get. Dylan serves up baffling lines (“You should be made to wear earphones!”), then mocks his baffled listeners for not being in on the joke. It’s also packed with homoerotic innuendo, from the naked man in the first verse to the sword swallower and the one-eyed midget who show up later on, maybe because nothing’s more certain to make strait-laced folks like Mr Jones uncomfortable. Dylan has addressed the question of the real Mr Jones’ identity many times over the years, but his most convincing answer came in 1985: “There were a lot of Mr Joneses at that time”¦ It was like, ”˜Oh, man, here’s the thousandth Mr Jones.’”

19. Blind Willie McTell
The Bootleg Series Vol. 1-3 (1991)

”˜Infidels’ producer-guitarist Mark Knopfler was reportedly shocked when Dylan cut this highlight from the album. Decades later, Dylan’s decision remains inscrutable: ”˜Blind Willie McTell’ is one of his few masterpieces from the early Eighties. Over blessedly spare instrumentation, he goes deep into the South of chain gangs, undertakers’ bells and “charcoal gypsy maidens.” It’s a chilling tribute to the real McTell ”“ who, like Dylan, was known for his never-ending tours. “I was born a rambler,” the late singer once said. “I’m gonna ramble till I die.”