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100 Greatest Bob Dylan Songs

From “Just Like a Woman” to “John Wesley Harding,” we count down the American icon’s key masterpieces

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

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As Bob Dylan turns 75, he shows no signs of slowing down. The American icon is gearing up for a summer tour with longtime friend Mavis Staples and has just released Fallen Angels, his 37th LP and second straight Sinatra-inspired album of American Songbook classics. For generations to come, other artists will be turning to Dylan’s own catalog for inspiration. From the Sixties protest anthems that made him a star through to his noirish Nineties masterpieces and beyond, no other contemporary songwriter has produced such a vast and profound body of work: songs that feel at once awesomely ancient and fiercely modern. Here, with commentary from Bono, Mick Jagger, Lenny Kravitz, Lucinda Williams, Sheryl Crow and other famous fans, are Dylan’s 100 greatest songs – just the tip of the iceberg for an artist of his stature.

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

Ted Russell/Polaris

9

“Visions of Johanna” (1966)

"Visions of Johanna" is a tour de force, a breakthrough not only for the writer but for the very possibilities of songwriting. An extended, impressionistic account of a woozy New York City night, rich in pictorial detail and erotic longing, the five long verses zigzag between Dylan's acute dissection of one woman, the tangible and available Louise, and his longing for an absent ideal. Johanna may not even be real. But she is an addiction. "It's extraordinary," Bono once said. "He writes this whole song seemingly about this one girl, with these remarkable descriptions of her, but this isn't the girl who's on his mind! It's somebody else!"

Dylan's masterpiece of obsession – written, ironically, shortly after his marriage in 1965 – was a passion in itself. He debuted the song in concert in December 1965, to an audience that included ex-paramour Joan Baez and poet Allen Ginsberg, then played it every night on the 1966 world tour – notably in the solo acoustic sets. A November '65 attempt to cut an electric "Johanna" with the Hawks (under the explicitly bitter title "Seems Like a Freeze Out") had run aground after 14 takes. The Hawks were still too much of a bar band; the song's confessional complexity required poise as well as muscle.

In contrast, Dylan nailed "Johanna" on the first take in Nashville. The local session pros, supplemented by Robbie Robertson's crying-treble guitar, brought the right unhurried empathy to Dylan's vocal mood swings – from a whisper to a howl at the moon in the same verse – and unforgettable lyric images.

"I still sing that song every once in a while," Dylan said in 1985. "It still stands up now as it did then. Maybe even more in some kind of weird way."

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

Ted Russell/Polaris

8

“Mr. Tambourine Man” (1965)

David Crosby: As far as I can tell, the Byrds' recording of "Mr. Tambourine Man" was the first time anyone put really good poetry on the radio. The Beatles hadn't gotten to "Eleanor Rigby" or "A Day in the Life" – they were still writing, "Ooh, baby." But Bob's lyrics were exquisite. "To dance beneath the diamond sky with one hand waving free" – that was the line that got me. I think he was finding himself as a poet.

I had seen Bob at Gerde's Folk City in New York years earlier. Everyone was talking about him. I thought, "Fuck, I can sing better than that. Why are they making all that fuss about him?" Then I started really listening. And I almost quit, right there. I think the Byrds were Bob's best translators. Bob did not envision this song the way we did it. When he came to the studio where we were rehearsing and heard us do "Mr. Tambourine Man," he was stoked. I think hearing our version was part of what made Dylan shift over to being a rocker. He thought, "Wait a minute, that's my song," and he heard how it could be different.

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

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7

“It’s Alright, Ma
 (I’m Only Bleeding)” (1965)

"I don't know how I got to write those songs," Dylan said in 2004, apropos of "It's Alright, Ma." "Try to sit down and write it. I did it once, and I can do other things now. But I can't do that."

Written in Woodstock in the summer of 1964, while his folk-scene compadres Joan Baez and Mimi and Richard Fariña were Dylan's houseguests, "It's Alright, Ma" is a transition from the politically minded lyrics that had briefly been Dylan's stock in trade to a broader vision of "life, and life only": Instead of pointing fingers at a particular flaw of culture, the song tears down the entire decrepit thing, declaring that all is vanity and hypocrisy and phony propaganda. On a purely technical level, "It's Alright, Ma (I'm Only Bleeding)" is dazzling, with an incredibly complicated rhyme scheme and a melody that barrels along on two notes until the flourish at the end of each verse. The lyrics incorporate nods to Arthur Koestler (author of Darkness at Noon), the Book of Ecclesiastes and even Dylan's beloved Elvis Presley (the title is just a hair shy of Presley's line "That's all right, now, Mama"). It's always been a tricky song to sing – a snapshot of a moment in his development, a jewel that he's lucky enough to own rather than a machine whose workings he understands. Talking about "It's Alright, Ma" in 1980, he described the difficulty of getting "in touch with the person you were when you wrote the songs… But I can still sing it, and I'm glad I've written it."

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

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6

“I Shall Be Released” (1971)

With its simple, evocative tale of a prisoner yearning for freedom, this rock hymn was part of a conscious effort by Dylan to move away from the sprawling imagery of his mid-Sixties masterpieces. "In '68 [Dylan told] … me how he was writing shorter lines, with every line meaning something," Allen Ginsberg once said. "From that time came some of the stuff … like 'I Shall Be Released.' … There was to be no wasted language." The result was one of Dylan's best-loved songs, first cut during the 1967 Basement Tapes sessions with the Band. The rough church of the organ and guitar frame Dylan's urgent nasal prayer, until Richard Manuel's keening harmony illuminates the chorus, like sunlight pouring through a stained-glass window. In the mid-Eighties, David Crosby sang that chorus to himself – "Any day now, any day now/I shall be released" – in his Texas prison cell, as he served nine months on drug and weapon charges. "I wrote it on the wall," he recalls. "It took me hours. But I did it. And I remember taking heart from it."

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EXCLUSIVE; SPECIAL RATES APPLY. Bob Dylan in his Greenwich Village apartment just a few months before he would release his self-titled debut album. (Ted Russell/Polaris) /// Bob Dylan

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5

“All Along the Watchtower” (1967)

You could say that jokes and theft are the twin poles of Dylan's art, and this 12-line masterpiece about a joker (who believes he's being robbed) and a thief (who thinks everything's a joke) penetrates to the core of his work. "Watchtower" is among Dylan's most haunting tunes: Built around an austere arrangement and Dylan's spooked croon, it starts like a ballad that's going to go on for a long while. But as soon as the joker and the thief get their opening statements, the song ends with an ominous image – two riders approaching – leaving listeners to fill in the blanks.

Jimi Hendrix's reading of "Watchtower" is one of the few Dylan covers that has permanently affected the way Dylan himself plays the song. Hendrix started recording his cover within weeks of John Wesley Harding's release, fleshing out the song into something stunningly intense. "He played [my songs] the way I would have done them if I was him," Dylan later said of Hendrix.