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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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For generations to come, other artists will be turning to Bob Dylan’s 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.

[This list originally appeared in a 2015 Special Edition]

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“Subterranean Homesick Blues” (1965)

The American Dream, according to Dylan: “Twenty years of schooling and they put you on the day shift.” And that’s if you get lucky, kid. “Subterranean Homesick Blues” was his first electric blast, released as a single in March 1965 and crashing the Top 40. Dylan delivers a proto-rap barrage of one-liners sending up America’s mixed-up confusion. “Look out, kid/ You’re gonna get hit,” Dylan advises, on the run from cops, teachers, the army and even meteorologists. (Although the radical group the Weathermen took their name from the song anyway.)

“It’s not folk rock, it’s just instruments,” Dylan explained in 1965 to the Chicago Daily News. “I’ve been on too many other streets to just do that.” And with “Subterranean Homesick Blues,” he made America’s streets sound scarier – and more exciting – than ever.

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“Desolation Row” (1965)

Mick Jagger: “Desolation Row” is so simple musically – just three chords for 11 minutes, with minimal accompaniment – yet it’s so effective. There’s Dylan, a bassist and a session guitar player, Charlie McCoy, from Nashville, who adds a nice little counterpoint to the melody. After many listenings, his playing still sounds sweet; I like the slight Spanish tinge of it. But it doesn’t get in the way of what is obviously the main thing: the vocal and the lyrics.

Dylan’s delivery is recitative, almost deadpan, but he engages you. What’s wonderful is all these characters he inveighs on our imagination: Famous people surrealistically appear, some of them mythical and some of them real. The Phantom of the Opera. Ezra Pound and T.S. Eliot. Cinderella. Bette Davis. Cain and Abel.

I love the bit about “Einstein, disguised as Robin Hood”: “You would not think to look at him, but he was famous long ago/For playing the electric violin on Desolation Row.” It’s a great image of Einstein – all his hair is jutting out, and he’s got the violin, which he used to play. Someone said “Desolation Row” is Dylan’s version of “The Waste Land.” I’m not sure if that’s true, but it’s a wonderful collection of imagery – a fantasy Bowery – that really gets your imagination working.

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“It’s All Over Now, Baby Blue” (1965)

In the film Don’t Look Back, Dylan sits around his room in London’s posh Savoy Hotel, surrounded by hangers-on. Bored, he picks up an acoustic guitar and plays a new song he’s just written: “It’s All Over Now, Baby Blue.” He has an evil grin on his face; after the first two verses, it’s the only smile in the room – everyone else looks shattered. The party’s definitely over.

The song is his devastating farewell to innocence, kicking Baby Blue out into the street, whether that means the end of a friendship or his abandonment of the folk scene. After he was famously booed offstage for going electric at the Newport Folk Festival, and returned with an acoustic guitar, this is the song he chose to play as his hard-ass response.

It instantly became one of his most covered songs. But nobody’s ever sung “Strike another match, go start anew” with the menace of Dylan himself.

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“Every Grain of Sand” (1981)

“It’s like one of the great Psalms of David,” Bono says about “Every Grain of Sand,” the spellbinding ballad from Shot of Love that concludes Dylan’s overtly Christian songwriting phase. Equal parts Blakean mysticism and biblical resonance, the song abandons the self-righteousness that plagued Dylan’s religious work to offer a desperate prayer for salvation. Shadowing Dylan on vocals is gospel great (and Dylan flame) Clydie King: “I get chills when I hear her just breathe,” Dylan said. “Every Grain of Sand” taps into a moving humility (“Sometimes I turn, there’s someone there, other times it’s only me,” he sings). As Bono puts it, “Dylan stops wailing against the world, turns on himself and is brought to his knees.”

Dylan later described “Every Grain of Sand” as “an inspired song that just came to me … I felt like I was just putting words down that were coming from somewhere else.”

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“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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“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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“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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“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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“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.

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“Just Like a Woman” (1966)

Dylan’s finest ballad is not a love song. “Just Like a Woman” is a complex portrait of adoration and disappointment, written as vengeance but sung as regret. Dylan never revealed a specific inspiration for the woman indicted. (Dylanologists often cite Andy Warhol’s star-crossed protégée Edie Sedgwick.) But the song is more about his own turbulent lessons in romance – the giving, taking and leaving. It is also Dylan’s first great country-rock performance. Dylan was making thunder and headlines onstage that year with the Hawks, but he cut this song with Nashville session cats who heard and heightened his tangle of rapture and despair. “There’s a lifetime of listening in these details,” songwriter Jimmy Webb said. “I still marvel at what an absolutely stunning piece of writing it is.”

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“Tangled Up in Blue” (1975)

“[This song] took me 10 years to live, and two years to write,” Dylan often said before playing “Tangled Up in Blue” in concert. His marriage was crumbling in 1974 as he wrote what would become the opener on Blood on the Tracks and his most personal examination of hurt and nostalgia. Dylan’s lyrical shifts in perspective, between confession and critique, and his acute references to the Sixties experience evoked a decade of utopian dreams and broken promise. His plaintive vocal and the fresh-air picking of the Minneapolis session players hearkened to an earlier pathos: the frank heartbreak and spiritual restoration in Appalachian balladry. Dylan has played this song many different ways live but rarely strays from the perfect crossroads of this recording, where emotional truths meet the everlasting comfort of the American folk song.

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“A Hard Rain’s A-Gonna Fall” (1963)

The greatest protest song by the greatest protest songwriter of his time: a seven-minute epic that warns against a coming apocalypse while cataloging horrific visions – gun-toting children, a tree dripping blood – with the wide-eyed fervor of John the Revelator. “Every line in it is actually the start of a whole song,” Dylan said at that time. “But when I wrote it, I thought I wouldn’t have enough time alive to write all those songs, so I put all I could into this one.”

The threat of nuclear war was in the air at the time, as other songs from the Freewheelin’ sessions – including “Talkin’ World War III Blues” and the anti-fallout-shelter rant “Let Me Die in My Footsteps” – make clear. But this rain was abstract rather than literal. “It’s not the fallout rain,” Dylan said. “I just mean some sort of end that’s just gotta happen.”

“A Hard Rain’s A-Gonna Fall” – that “a-gonna” was the young Dylan’s Woody Guthrie fixation popping out again – began life as a poem, which Dylan likely banged out on a typewriter owned by his buddy (and fellow Greenwich Village dweller) Wavy Gravy. Dylan debuted the song at Carnegie Hall in September 1962, when he was part of a folk-heavy bill in which each act got 10 minutes: “Bob raised his hand and said, ‘What am I supposed to do? One of my songs is 10 minutes long,'” said Pete Seeger, the concert’s organizer.

“A Hard Rain” is the first public instance of Dylan grappling with the End of Days, a topic that would come to dominate his work. But the tumbling verses of “A Hard Rain” culminate not in catastrophe but in Dylan describing his task as an artist: to sing out against darkness wherever he sees it – to “tell it and think it and speak it and breathe it” until his lungs burst. “It’s beyond genius,” says the Grateful Dead’s Bob Weir. “I think the heavens opened and something channeled through him.”

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“Like a Rolling Stone” (1965)

Bono: That sneer – it’s something to behold. Elvis had a sneer, of course. And the Rolling Stones had a sneer that, if you note the title of the song, Bob wasn’t unaware of. But Bob Dylan’s sneer on “Like a Rolling Stone” turns the wine to vinegar.

It’s a black eye of a pop song. The verbal pugilism cracks open songwriting for a generation and leaves the listener on the canvas. “Rolling Stone” is the birth of an iconoclast that will give the rock era its greatest voice and vandal. This is Dylan as the Jeremiah of the heart. Having railed against the hypocrisies of the body politic, he starts to pick on enemies that are a little more familiar: the scene, high society, “pretty people” who think they’ve “got it made.” He hasn’t made it to his own hypocrisies – that would come later. But the “us” and “them” are not so clearly defined as earlier albums. Here he bares his teeth at the hipsters, the idea that you had a better value system if you were wearing the right pair of boots.

For some, the Sixties was a revolution. But there were others who were erecting a guillotine in Greenwich Village not for their political enemies, but rather for the squares. Bob was already turning on that idea, even as he best embodied it, with the corkscrew hair Jimi Hendrix imitated. The tumble of words, images, ire and spleen on “Rolling Stone” shape-shifts easily into music forms 10 or 20 years away, like punk, grunge or hip-hop. Looking at the character in the lyric, you ask, “How quickly could she have plunged from high society to ‘scrounging’ for her ‘next meal’?” Perhaps it is a glance into the future; perhaps it’s fiction, a screenplay distilled into one song.

It must have been hard to be or be around Dylan then; that unblinking eye was turning on everybody and everything. But the real mischief is in its ear-biting humor. “If you ain’t got nothing, you got nothing to lose” is the T-shirt. But the line that I like the best is “You never turned around to see the frowns on the jugglers and the clowns/When they all did tricks for you/You never understood that it ain’t no good/You shouldn’t let other people get your kicks for you.”

The playing on this track – by the likes of guitarist Mike Bloomfield and keyboardist Al Kooper – is so alive that it’s like you’re getting to see the paint splash the canvas. As is often the case with Bob in the studio, the musicians don’t fully know the song. It’s like the first touch. They’re getting to know it, and you can feel their joy of discovery as they’re experiencing it.
When the desire to communicate is met with an equal and opposite urge not to compromise in order to communicate is when everything happens with rock & roll. And that’s what Dylan achieved in “Rolling Stone.” I don’t particularly care who this song is about – though I’ve met a few people who have claimed it was about them (some who weren’t even born in 1965). The thrill for me was that “once upon a time,” a song this radical was a hit on the radio. The world was changed by somebody who cared enough about an unrequited love to write such a devastating put-down.
I love to hear a song that changes everything. That’s the reason I’m in a band: David Bowie’s “Heroes,” Arcade Fire’s “Rebellion (Lies),” Joy Division’s “Love Will Tear Us Apart,” Marvin Gaye’s “Sexual Healing,” Nirvana’s “Smells Like Teen Spirit,” Public Enemy’s “Fight the Power.” But at the top of this dysfunctional family tree sits the king of spitting fire himself, the juggler of beauty and truth, our own Willy Shakespeare in a polka-dot shirt. It’s why every songwriter after him carries his baggage and why this lowly Irish bard would proudly carry his luggage. Any day.