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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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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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29

“You Ain’t Goin’ Nowhere” (1971)

How did Dylan spend the Summer of Love? Holed up in a basement in upstate New York, making strange demos with his friends in the Band, singing this stoic warning about tough times ahead: "Strap yourself to the tree with roots/You ain't goin' nowhere." The first time most people heard "You Ain't Goin' Nowhere" was in the Byrds' straight country rendition on 1968's Sweetheart of the Rodeo. Dylan released it later as one of the new tracks on his Greatest Hits Vol. II, turning it into a good-time banjo shuffle and adding a sly riposte to the Byrds' Roger McGuinn: "Gonna see a movie called Gunga Din/Pack up your money, and pull up your tent, McGuinn." The definitive Basement Tapes version is mysterious, doomy, yet somehow still festive. In an outtake, he sings it as a stoned lullaby, apparently addressed to his housemates: "Look here, dear soup, you'd best feed the cats/ The cats need feeding and you're the one to do it." He left the cats out of later versions, but kept the song's playful spirit.

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28

“The Times They Are A-Changin'” (1964)

When people describe Dylan as the "spokesman of a generation," they are thinking of the man best defined by "The Times They Are A-Changin'." And while Dylan would later bluntly reject that title, he consciously sought it with this passionate anthem. A masterpiece of political songwriting, it addresses no specific issue and prescribes no concrete action, but simply observes a world in violent upheaval. (That the song was released just months after the assassination of John F. Kennedy only lent it more power.) Dylan sings in the voice of a bard or prophet, in cadences that are clearly biblical – in his words, "short, concise verses that piled up on each other in a hypnotic way."

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27

“Sad-Eyed Lady of the Lowlands” (1966)

In his 1976 classic "Sara," Dylan explained this song as a tribute to his first wife, whom he had secretly married just months before starting work on Blonde on Blonde. "Staying up for days in the Chelsea Hotel," he sang wistfully, "writing 'Sad-Eyed Lady of the Lowlands' for you." Like so many stories about Dylan's past, the anecdote from "Sara" is both fascinating and mostly false. "Sad-Eyed Lady of the Lowlands" is indeed an ode to Sara Dylan, but he largely wrote it on the spot during the dead of night in a Nashville studio. While the session musicians he'd hired played cards, he sat down and wrote the sweetly surreal verses. "It started out as just a little thing," Dylan said in 1969. "But I got carried away somewhere along the line."

After eight hours of work, Dylan called the band members into the studio at 4 a.m. and gave them minimal instructions. They had no idea the song would keep going for 11 minutes – and they were stunned once more when, afterward, Dylan told them they had nailed it on the very first take.

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26

“Masters of War” (1963)

"Masters of War" is Dylan's angriest protest song. His starting point seems to be the fears of nuclear holocaust – but characteristically, Dylan took that common theme and gave it a crucial twist. Where typical anti-war songs might indict politicians or generals, Dylan's target is the military-industrial complex itself: Greed drives the masters of war, not ideology. "Is your money that good?" Dylan spits out as he envisions a world awash in blood. "Will it buy you forgiveness?" The song ends with the singer calling out for the deaths of those bomb builders, promising to stand over their graves "till I'm sure that you're dead." "I don't sing songs which hope people will die," Dylan observed at the time. "But I couldn't help it with this one."

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25

“Knockin’ on Heaven’s Door” (1973)

Always a fan of westerns (and outlaws of every stripe), Dylan wrote a handful of songs for Sam Peckinpah's 1973 film, Pat Garrett & Billy the Kid. Jerry Fielding, a composer brought in to help Dylan with the music, described his reaction to hearing this heartbreaking sketch of a dying lawman: "It was shit. That was the end for me." Dylan, of course, had the last laugh. "Knockin' on Heaven's Door" became a Number 12 hit and one of his most-covered songs. Musically, it's also one of his simplest compositions – if you can play four easy chords and remember seven lines, you've got it down – which may be why, when a guest star shows up for the encore at a Dylan show, this is often the song that gets performed.

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24

“Lay, Lady, Lay” (1969)

Lenny Kravitz: I first heard "Lay, Lady, Lay" when I was six or seven, riding around New York in the back seat of my parents' old VW Bug, listening to WABC. It was the first Bob Dylan song I remember loving. Later, when I heard another one of his songs, I wondered, "Where's that low, crooning voice?" He's singing it in a very different voice from his normal one. I thought this guy sounded like that all the time!

It's a very black song – very soulful and sensual. "Lay across my big brass bed" is a lyric you would expect to hear from Isaac Hayes. The beautiful thing about Dylan is that he is such a chameleon. He's got so many characters inside of him, like a painter with limitless amounts of color. I love the vocal. I love the descending chord progression. I love the drum fills. It's a simple, beautiful love song, and I love the whole feel of it.

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23

“Forever Young” (1974)

Dylan recorded this folksy prayer twice with the Band – as a sparkling ballad version that closed Side One of Planet Waves, and a stomping country-rock take that kicked off Side Two. Lyrics like "May you have a strong foundation/When the winds of changes shift" are as universal and uplifting as Dylan has ever written; they also work as a blessing for a generation coming out of a post-Sixties cultural hangover. Dylan said he wrote it for his son Jesse; others see it as a nod to Neil Young, who scored a Number One hit in 1972 with "Heart of Gold."

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22

“Don’t Think Twice, It’s All Right” (1963)

In 1962, Dylan was heartbroken after Suze Rotolo, his first serious girlfriend, left New York for an open-ended stay in Italy. Out of that pain came this classic breakup ballad, in which he reels from a desperate sense of abandonment to a sharp bitterness ("You just kinda wasted my precious time"). "It isn't a love song," he wrote in the liner notes to The Freewheelin' Bob Dylan. "It's a statement that maybe you can say to make yourself feel better. It's as if you were talking to yourself." Dylan borrowed the song's melody from folk singer Paul Clayton (who had himself adapted it from the earlier tune "Scarlet Ribbons for Her Hair"), later settling out of court when Clayton filed a claim against him. But a poultry supplier near Dylan and Rotolo's former Greenwich Village apartment inspired one key image: "When your rooster crows at the break of dawn/Look out your window, and I'll be gone." As Rotolo recalled in her 2008 memoir, "When Bob and I stayed up all night … we heard the roosters crowing at the break of dawn."

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21

“Mississippi” (2001)

Sheryl Crow: I released "Mississippi" before Dylan did, on my album The Globe Sessions. It changed the whole record. There's no fat in the song – every line has a purpose. He said that he liked every line of his songs to have the possibility of being the first line of a new song. That's certainly the case with "Mississippi." He gets very philosophical about aging, telling a story about redemption and resolution for the Everyman in a way that's almost biblical: "Well, my ship's been split to splinters and it's sinkin' fast/I'm drownin' in the poison, got no future, got no past/But my heart is not weary, it's light and it's free."

It's Dylan writing like a short story writer, like Steinbeck or Mark Twain – creating a story, but making these classical, sweeping statements. "Mississippi" is our introduction to Dylan as somebody facing mortality with an upbeat attitude. Bob Dylan may have turned 70 a couple of years ago, but he never gets older to me. That's what mythological characters are all about.

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20

“Blowin’ in the Wind” (1963)

The song that first branded Dylan a prophet asks nine questions and answers none. Dylan claimed it took only 10 minutes to knock out this meditation on humanity's inhumanity, a rewrite of the anti-slavery spiritual "No More Auction Block." The version most people heard in 1963 wasn't Dylan's – it was Peter, Paul and Mary's cover, which hit Number Two on the pop chart. But in any version, the words are so simple, it sounds like they're handed down from the sky on stone tablets. "It's absolutely wonderful writing," says Merle Haggard. "It was timely then and is still timely today."

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19

“Blind Willie McTell” (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."

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18

“Ballad of a Thin Man” (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 straight-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.'"

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17

“This Wheel’s on Fire” (1975)

A kaleidoscopic evocation of chaos that can suggest anything from the Vietnam War 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 1967 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 favors done") will be avenged in full in the future. 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 managed to catch 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 album, Dr. Byrds & Mr. Hyde: Clarence White's searing fuzz guitar sounds like apocalypse arrived.

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16

“Positively 4th Street” (1967)

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 Los Angeles. It just didn't work. Once we were playing somewhere, and I ran into a friend I knew 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 exactly what "Positively 4th Street" is about. I love the way the song closes: "I wish that for just one time, you could stand inside my shoes/You'd know what a drag it is to see you." Those lines feel so good to sing. I've heard that Dylan wrote the song when he started getting famous and he was still living in the Village in New York. Nobody wants to admit that that kind of stuff goes on, and of course nobody knows anything about what it's really like to be Bob Dylan. There's only one of him. And he's so damn good at that.

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15

“Simple Twist of Fate” (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.

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14

“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."

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13

“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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12

“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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11

“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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10

“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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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."