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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

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68

“One Too Many Mornings” (1964)

"One Too Many Mornings" is an achingly pretty breakup song – and the rare tune where Dylan bid fare-thee-well without assigning any blame. It's as subdued a song as any in Dylan's catalog – just gentle acoustic picking, harmonica and a spare, resigned vocal. Likely another tune inspired by his relationship with Suze Rotolo, it comes off like a gentler version of "Don't Think Twice, It's All Right." Dylan is leaving his bedroom, the street is ahead of him, when he looks back with a conciliatory goodbye: "You're right from your side/I'm right from mine." "One Too Many Mornings" proved ripe for revisiting, both by Dylan (whose electric version on his 1966 tour turned the gentle tune into something like punk rock) and by Johnny Cash, who recorded the song four times – twice with Dylan (in separate versions from the Nashville Skyline sessions), once with Waylon Jennings and once on his own.

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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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67

“Leopard-Skin Pill-Box Hat” (1966)

Not many songs about sexual jealousy are as hilarious as this loping, snarling 12-bar Chicago-style blues number. The Blonde on Blonde recording has the loose, stumbling tone of a one-take throwaway, but in fact Dylan uncharacteristically took 22 different stabs at "Leopard-Skin Pill-Box Hat" over the course of four sessions in six weeks; an earlier, slower ramble through it can be found on the No Direction Home soundtrack.
 It's a little masterpiece of inside-out innuendo and twisted double-entendre: the drunken hookup implicit in "just like a mattress balances on a bottle of wine," an invitation to see the sun rise, followed by "We'll both just sit there and stare." And who's the victim of Dylan's invective here? Rumors suggest that it's fashionable-hat-wearer Edie Sedgwick, with whom he'd been spending time not long before. When asked about the inspiration in Rolling Stone, Dylan was typically cagey, saying the song was just about a hat: "Mighta seen a picture of one in a department store window."

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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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66

“Shelter From the Storm” (1975)

The twin moods of "Shelter From the Storm" are best captured in two wildly different performances. On Blood on the Tracks, the song is an acoustic reflection on a relationship mysteriously gone bad, a fond remembrance of a woman who, for all her faults, provided the singer a respite, however brief, from the world's trials. On the live album Hard Rain, meanwhile, the song is a roaring rock & roll juggernaut, a sneering denunciation of a hypocritical lover whose offer of a warm, safe haven is dismissed as a cynical joke.
 Encompassing such emotional extremes within a single song is one of Dylan's most distinctive gifts – in this case, a song that took shape as his marriage to Sara was disintegrating. "Beauty walks a razor's edge," he sings, and as the song makes clear, when you pursue it, you sometimes bleed.

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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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65

“Tough Mama” (1974)

One of Dylan's horniest jams was recorded in November 1973, with the Band cranking up a killer boogie-rock groove. The character list reads like something off the Workingman's Dead lyric sheet: There's Jack the Cowboy, the Lone Wolf and the title hottie, alternately known as Tough Mama, Dark Beauty, Sweet Goddess and Silver Angel. Yet the poetic derangement is all Dylan in lines like "Today on the countryside it was a-hotter than a crotch/I stood alone upon the ridge and all I did was watch." Maybe that's why, compared to the man's other great rockers, it's rarely been covered – after all, few can out-derange Dylan.

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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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64

“Abandoned Love” (1985)

A mid-Seventies castoff, with Scarlet Rivera's fiddle carving up the melody across a loose, bouncy country two-step. The lyrics, however, are no tea dance: a chain of couplets that keep cinching tighter as they chart a destroyed relationship in cutting detail. "Everybody's wearing a disguise/To hide what they've got left behind their eyes," Dylan wails. "But me, I can't cover what I am/Wherever the children go I'll follow them." Recorded in 1975, it was dropped from the Desire LP in favor of "Joey." But "Abandoned Love" eventually surfaced on Biograph, where it was revealed as one of Dylan's most tortured, heartbroken recordings.

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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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63

“If You See Her, Say Hello” (1975)

"If You See Her, Say Hello" might be the most painful moment on Blood on the Tracks. Dylan is grappling with fresh grief: "To think of how she left that night," he sings, "it still brings me a chill." The song went through extensive revisions – an early draft's "If you're making love to her, kiss her for the kid" was softened to "If you get close to her, kiss her once for me." But the final version still cuts close to the bone. Hearing Dylan admit "Either I'm too sensitive or else I'm gettin' soft" packs just as much punch as his most venomous songs.

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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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62

“Queen Jane Approximately” (1965)

Joan Baez once referred to Highway 61 Revisited as a "bunch of crap." She may have been commenting on the raucous sound; she may also have been thinking of this song, a takedown of a woman cloistered by beauty and privilege. "Queen Jane" goes from caustic ("When all the clowns that you have commissioned have died in battle or in vain") to tender ("Won't you come see me, Queen Jane?"), and the music is some of the most elegant on Highway. Is the song about Baez? Maybe. When a journalist asked him about the queen's identity, Dylan shot back, "Queen Jane is a man."

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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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61

“It Takes a Lot to Laugh, It Takes a Train to Cry” (1965)

This sexy shuffle was still a hopped-up blues called "Phantom Engineer" when Dylan debuted it at the 1965 Newport Folk Festival. Later, it was the first song he attempted during the sessions for Highway 61 Revisited – but Dylan, frustrated with the arrangement, set it aside after a few takes and cut "Tombstone Blues" instead. He spent his lunch break at the piano, working out a slower version that let him linger over the lyrics' blues tropes ("Don't the moon look good, Mama, shinin' through the trees") and sly asides ("I wanna be your lover, baby, I don't wanna be your boss"). The results felt both timeless and brand-new.

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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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60

“Buckets of Rain” (1975)

Cameron Crowe: One of the great gifts Bob Dylan has is to slip a grace note into an album, something that doesn't cry out to be noticed but is unforgettable.

To me, that's "Buckets of Rain," the perfect grace note for Blood on the Tracks: melancholy, loping and bittersweet. It's sly and unpretentious, but has huge power. Any room I've ever played it in has changed as a result. One little thing in the corner of an album, a movie or any piece of writing can be the most important element of all.

Dylan was in his middle period when he wrote it. I heard he went back to Minnesota and was living on a farm. He had a notebook, and the lyrics of Blood on the Tracks were honed in that period. He was going to get personal. It was going to hurt to hear, but it was going to be revelatory. It turned out to be the confessional Dylan album that people had been craving for a long time, and he hasn't really gone back there since. He put up a lot of roadblocks and disinformation about it, but Blood on the Tracks is his Blue – his confessional album about relationships. I can't think of it without "Buckets of Rain." Dylan's stuff continues to inform every generation – it just lives and lives and lives, and a song like "Buckets of Rain" breathes with a simple truth about real life. After a blistering heartache comes a soothing rain.

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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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59

“Million Dollar Bash” (1975)

"Million Dollar Bash" is a theme song of sorts for The Basement Tapes: a playful string of nonsense lyrics set to a sweet, off-kilter melody that captures the spirit of people playing music purely for the fun of it. Dylan recorded it at Big Pink in July 1967 with the Band's Garth Hudson, Richard Manuel and Rick Danko. No one drums on the track, which partly accounts for its gleeful, teetering rhythms. Those basement sessions can themselves be thought of as a "Million Dollar Bash" – a joyful, restorative break from the madness of Dylan's increasing fame. As he told Rolling Stone in 1969, "That's really the way to do a recording – in a peaceful, relaxed setting – in somebody's basement. With the windows open… and a dog lying on the floor."

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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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58

“Percy’s Song” (1985)

Perhaps best known from Joan Baez's scene-stealing performance in Don't Look Back, "Percy's Song" was originally recorded for The Times They Are A-Changin' in 1963 but didn't make the final track list. Even so, this mournful lament stands up beside Dylan's finest work from that era. He sings in haunted tones of a friend who is on trial for manslaughter after a fatal car crash. "He ain't no criminal, and his crime it is none," the narrator protests, but his pleas to the judge for leniency are all in vain.

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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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57

“Just Like Tom Thumb’s Blues” (1965)

Had Dylan even visited Mexico prior to penning this tale of a dissolute trip to Juárez? Does it matter? Dylan's version of the border town is a dangerous, yet alluring, place. It's rife with drugs, corruption and "hungry women" like Saint Annie and Sweet Melinda – whose innocent names belie the fact that "they really make a mess outta you." The song took on an even more sinister vibe when Dylan performed it with the Hawks on his 1966 world tour. A vicious live take from Liverpool, released as a B side to "I Want You," was for many years the only official documentation of that historically raucous tour.

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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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56

“You’re Gonna Make Me Lonesome When You Go” (1975)

Jim James: Blood on the Tracks has always been one of my favorite Dylan records – it's the classic tough-love album to turn to when you're feeling kind of alone. "You're Gonna Make Me Lonesome When You Go" might win my repeat-listening award. I don't know if it's just the acoustic guitar and the bass, the way they work together rhythmically, but when I hear the song, it's just the essence of love. He's describing everything so viscerally. I can almost smell the trees and different people I've known over the years, the flowers, the sunlight – the way things look when you're falling in love and how that turns in on itself when you have to leave or move on or life changes you or changes the other person. He's reflecting on it in such a beautiful way, saying that person will always be a part of him. He'll see her everywhere.

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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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55

“If Not for You” (1970)

After the conceptual and critical disaster that was Self-Portrait (Rolling Stone review: "What is this shit?"), fans wondered if Dylan had lost it. They didn't wonder long – New Morning, released four months later, opened with this lovely little country-rock tune. "I wrote the song thinking about my wife," Dylan said, and its lyrics are about domesticity and gratitude. Hearing the cockiest songwriter alive showing a little humility for a change is a treat.

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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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54

“4th Time Around” (1966)

What exactly inspired "4th Time Around" is one of the great Dylan mysteries. The melody and story line are a direct takeoff of the 1965 Beatles song "Norwegian Wood" – among the band's first songs with a clear Dylan influence. Was the line "I never asked for your crutch, now don't ask for mine" a warning to stop ripping him off? Dylan's never said, but three months after he recorded it, he went on a famously stoned limo ride with John Lennon around London and didn't seem to be harboring any malice. The next year he released John Wesley Harding, which has what appears to be an upside-down image of the Beatles hidden in a tree on the cover – but that's another mystery.

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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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53

“When I Paint My Masterpiece” (1971)

Probably the least irritating song ever written about the life of a superstar on the road, Dylan's studio version surfaced in late 1971 among the unreleased material on Greatest Hits Vol. II. Produced by Leon Russell, the track lays gospel piano chords under a lament about awaiting inspiration in between gigs, aimless wandering, fame-related hassles and "a date with Botticelli's niece." The definitive version was recorded live with the Band on New Year's Eve 1971 and released on the Band's Rock of Ages. "Sailin' round the world in a dirty gondola," he hollered, "oh, to be back in the land of Coca-Cola!" wringing more emotion out of a brand name than anyone before or since.

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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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52

“Tears of Rage” (1975)

This mesmerizing ballad first came to the world's attention as the opening track on the Band's 1968 masterpiece, Music From Big Pink. There it is sung with agonizing grace by keyboardist Richard Manuel, who co-wrote the song with Dylan during the 1967 sessions at Big Pink. When The Basement Tapes officially came out in 1975, a version with Dylan singing lead came to light. Like so many of the songs Dylan wrote at Big Pink, "Tears of Rage" is elliptical, a string of casually surreal images that draw on the Bible and, in this case, Shakespeare's King Lear. Its tale of generational strife, tone of betrayal and opening reference to Independence Day suggest that the culture wars over Vietnam and civil rights were also on Dylan's mind. The song's repeated reminders that "life is brief" rise above cliché to a desperate moral calling, an insistence that, whatever our differences, our shared mortality must make for compassion.

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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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51

“Things Have Changed” (2000)

In 2001, when Dylan accepted his one and only Oscar for this contribution to the Wonder Boys soundtrack, he thanked "the members of the Academy who were bold enough to give me this award for … a song that doesn't pussyfoot around nor turn a blind eye to human nature." That's one way of putting it: For all its offhand jokes ("gonna dress in draaag," he rasps at one point), "Things Have Changed" is one of the bitterest songs in Dylan's entire catalog. It's also a harsh riposte to many of his own earlier political songs, with their longing for social justice and societal progress; "I used to care," he sings with unmistakable intent. "But things have changed." As the title suggests, it's basically the evil twin of "The Times They Are A-Changin'."

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