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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.

Bob Dylan; 100 Best Songs

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100

“Señor (Tales of Yankee Power)” (1978)

Dylan said this baffling-yet-haunting country-rock epic was inspired by a man he saw on a train ride from Mexico to San Diego: "He must have been 150 years old… Both his eyes were burning, and there was smoke coming out of his nostrils." Sounds rough. But, hey, at least the guy got to meet Bob Dylan.

Bob Dylan; 100 Best Songs

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99

“John Wesley Harding” (1967)

"I was gonna write a ballad," Dylan told Rolling Stone's Jann Wenner. "Like maybe one of those old cowboy [songs]… you know, a real long ballad." Instead, the title track on his 1967 album was a taut parable about outlaw morality. John Wesley Hardin was a late-19th-century badman, but Dylan's evocation of a "friend to the poor" who "was never known to hurt an honest man" is less about a particular character than celebrating a rugged American past that fit the rootsy turn his music was taking. Recorded in Nashville with drummer Kenny Buttrey and bassist Charlie McCoy, it's a masterwork of ascetic idealism.

Bob Dylan; 100 Best Songs

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98

“Corrina, Corrina” (1963)

"Corrina, Corrina" is an early example of Dylan's ability to place folk music in a wider pop tradition, and vice versa. The song had been a blues and country standard, under various titles for decades, recorded by Blind Lemon Jefferson, Chet Atkins, Big Joe Turner and teen crooner Ray Peterson, among others, usually as a fun dance tune. Dylan does it as a somber, pastoral ballad, adding an allusion to Robert Johnson's "Stones in My Passway" that deepens his sense of lovelorn depletion. But as tender as it was, "Corrina" also hints at his rock & roll heart: It's one of the first songs on a Dylan record that has drums on it.

Bob Dylan; 100 Best Songs

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97

“Where Are You Tonight? (Journey Through Dark Heat)” (1978)

The last track on a Dylan album is often a kind of preview of his next record – check the way John Wesley Harding‘s “I’ll Be Your Baby Tonight” is a trailer for the country sound of Nashville Skyline. The elegiac “Where Are You Tonight?” ends Street Legal by foretelling the conversion to Christianity that began on 1979’s Slow Train Coming. “I couldn’t tell her what my private thoughts were,” Dylan sings, worried his woman won’t be able to follow him to his “new day at dawn.” He’d reached a place few fans would have ever predicted either.

Bob Dylan; 100 Best Songs

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96

“Farewell, Angelina” (1991)

This outtake from Bringing It All Back Home contains some of Dylan's most evocative lyrics, a pileup of images that includes dancing elves, King Kong, cross-eyed pirates, 52 gypsies, a sky that's "flooding over" and fiends who "nail time bombs/To the hands of the clocks." But it's also a beautifully sung goodbye song to a girl – and maybe also to Dylan's more literal folk-era songwriting style. Presumably based on a Scottish folk song, "Farewell to Tarwathie," it's best known as a signature cover by Joan Baez. Along with the lyrical hot-wiring, Dylan's original added a melody that's as ominous as it is consoling.

Bob Dylan; 100 Best Songs

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95

“On a Night Like This” (1974)

This song kicks off Planet Waves – his reunion with the Band – on a rollicking, high-spirited note. As a galloping rhythm and a cantina accordion egg him on, Dylan sounds so giddy he can't quite talk straight – especially when he instructs his lover to "heat up some coffee grounds." Conjuring a snowbound cabin scene, "On a Night Like This" recalls the Basement Tapes days in upstate New York in both form and content, evoking a recent past when Dylan and the Band seemed able to explore every nook and cranny of American music. "We got much to talk about/And much to reminisce," he sings. It may have been a short-lived reunion. But it was a sweet one.

Bob Dylan; 100 Best Songs

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94

“Highlands” (1997)

Many of Dylan's greatest albums end with an epic that takes up the entire side of a record, and "Highlands" is the most epic of them all. Over the course of 16 minutes, Dylan talks to a waitress, orders softboiled eggs, name-checks Erica Jong and Neil Young and laments that life is passing him by. "All the young men with their young women looking so good," he sings. "Well, I'd trade places with any of them in a minute, if I could." He was only 56 when Time Out of Mind came out, but the fear of death is all over the album. Dylan has claimed that "Highlands" is built around a Charlie Patton riff, but nobody has found any riff that sounds remotely like it.

Bob Dylan; 100 Best Songs

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93

“Pay in Blood” (2012)

Dylan said he had planned to record his first religious album in years before heading into Jackson Browne's L.A. studio with his touring band in early 2012. Instead, he kicked off the sixth decade of his career with Tempest, a brutally intense record steeped in a specifically American strain of violence and tragedy. "Pay in Blood" is swaggering and murderous; over an Exile-era Stones-y riff, Dylan spews cruel venom: "I'll drink my fill and sleep alone/I pay in blood but not my own." He could be a slave owner, a gunslinger or a politician. "It's called tradition," Dylan told Rolling Stone, describing the album. "And that's what I deal in."

Bob Dylan; 100 Best Songs

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92

“Going, Going, Gone” (1974)

Despite all the mythology surrounding Dylan's work with the Band, he only actually recorded a single album with them. Cut in Los Angeles over four frantic days in 1973, Planet Waves varies from light, vigorous tunes like "You Angel You" to the brooding, aptly titled "Dirge." The album's high point, "Going, Going, Gone," is a wearily elegant intimation of suicide that's musically full of life – Robbie Robertson's guitar work has never been tighter, and Garth Hudson's organ radiates churchy beauty. Dylan's vocals have a rough urgency he struggled through several takes to get right; on one scrapped version he even used vocal overdubs for the first time in his career.

Bob Dylan; 100 Best Songs

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91

“You’re a Big Girl Now” (1975)

Is there a more desperately lovesick moment in Dylan's entire catalog than the point in this Blood on the Tracks gem when he croons, "I can change, I swear," and then howls like a wounded dog? Maybe only later in the same song, when he talks of "pain that stops and starts, like a corkscrew to my heart." Dylan's stunning first pass at this, the hushed New York outtake included on Biograph, sounds wounded. But here, the pain is even sharper. "I read that this was supposed to be about my wife," Dylan wrote in the Biograph liner notes, hoping to clarify the matter. "I don't write confessional songs… It only seems so, like it seems that Laurence Olivier is Hamlet."

Bob Dylan; 100 Best Songs

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90

“The Groom’s Still Waiting at the Altar” (1981)

Todd Snider: Bob Dylan finds a million different ways to do one-four-five blues, Chuck Berry-style rock & roll, my favorite kind of song. I think there's a story getting told here that I don't totally understand, but who cares? It's just a great poem. I have no idea what the groom's still waiting at the altar for, but I feel terrible for him. Dylan invented this kind of song, where each verse has some wisdom being imparted without being preachy, like, "I know God has mercy on those that are slandered and humiliated," and, "I see people who are supposed to know better than to stand around like furniture." It's perfect. I wish I had thought of it.

But people that try to copy him end up looking ridiculous. A whole generation tried; they fucking Strawberry Alarm Clocked themselves to death. I still try to copy him, and it's like trying to steal something from somebody's house and everything in the house weighs 4,000 pounds. You're like, "Shit, how am I gonna get this out of here?" And you just can't. I opened up for him a little bit in the Eighties; I got to sit onstage and watch him sing, and it was incredible. He was drinking a lot, but it didn't seem to hurt him too much. Around the Eighties, people started saying he wasn't doing good stuff. The production sort of sounds like Phil Collins and shit; it reminds me of when I had just gotten out of high school, a time that kind of hurts the heart a little, I guess. I thought those albums were monsters.

Bob Dylan; 100 Best Songs

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89

“Changing of the Guards” (1978)

There are some pretty bizarre lyrics in the Bob Dylan catalog, but nothing quite like the opening track from 1978's Street Legal. "They shaved her head," Dylan sings against a dense layer of R&B backup singers and neon-dream saxophone. "She was torn between Jupiter and Apollo." The song is full of references to tarot cards, and some Dylan geeks see it as a look back at his own life since changing his name to Bob Dylan and moving to New York. Whatever the case, it's one of his all-time great forgotten Seventies works, precisely because it's so open to interpretation; for one powerful reading, see Patti Smith's mordant, politically tinged take from 2007.

Bob Dylan; 100 Best Songs

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88

“Tombstone Blues” (1965)

Dylan claimed this  breakneck jeremiad against violence-gorged American political culture was influenced by conversations he heard at a bar that was frequented by police officers. "They'd be saying stuff like, 'I don't know who killed him, but I'm glad he's gone,' that type of thing," he said. That murky yet matter-of-fact sense of lawless brutality and systemic evil infuses lyrics in which John the Baptist plays torturer and Jack the Ripper sits at the head of the chamber of commerce. Musically, "Tombstone Blues" is just as vicious, with guitarist Mike Bloomfield echoing Dylan's torrential lyrical flow with brash, searing, Chicago-steeped blues fire.

Bob Dylan; 100 Best Songs

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87

“Most of the Time” (1989)

Like many of the songs on Oh Mercy, "Most of the Time" had a difficult birth. Dylan envisioned it as a stripped-down folk song, but Daniel Lanois wanted to infuse it with his trademark swamp atmosphere production. Lanois won the battle, leaving Dylan to release his original on 2008's The Bootleg Series 8: Tell Tale Signs. The song explores the difficulty of getting over an old lover ("Don't even remember what her lips felt like on mine/Most of the time"), and both versions have their charms – yet while Dylan's original has a soul-baring immediacy, Lanois' slow, swelling track makes heartbreak seem like a real-time revelation.

Bob Dylan; 100 Best Songs

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86

“Meet Me in the Morning” (1975)

This sad, sparkling acoustic blues from Blood on the Tracks is remarkably straightforward – like comfort food by a master chef. Recorded in New York, it peaks with a pained pedal steel outburst by Buddy Cage, who per legend was being goaded in the studio by Dylan while a tipsy Mick Jagger, partying in the control room, begged to join in. Dylan never performed the song live until a 2007 Nashville gig, when Jack White lent a hand with the vocals. Dylan recorded the very similar "Call Letter Blues" around the same time (see The Bootleg Series, Vol. 1-3), proving the idea was good enough for two songs.

Bob Dylan; 100 Best Songs

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85

“She’s Your Lover Now” (1991)

Mid-Sixties Dylan was a pretty caustic guy, but there's something uniquely wicked in this speedily rocking, offhandedly catty Blonde on Blonde outtake. "You, you just sit around and ask for ashtrays/Can't you reach?" he snarls to his former lover's new man. "I see you kiss her on the cheek ev'ry time she gives a speech." Dylan and the Band cut the song 19 different times in New York in January 1966, but most of those sessions were scrapped when Dylan decided to move the album's recording down to Nashville. He never attempted to salvage it with the session pros he used there, but the playing on the extant demo (augmented by many alternate takes on the collector's edition of 2015's The Bootleg Series Vol. 12: The Cutting Edge 1965-1966) has just the right kind of casual edge.

Bob Dylan; 100 Best Songs

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84

“The Man in Me” (1970)

Sometimes it takes the right movie to expose the greatness of a song. Before the Coen brothers' 1998 cult classic, The Big Lebowski, "The Man in Me" was a half-forgotten track on 1970's New Morning. But its use in the film (in the opening credits and later in an epic dream sequence) highlighted its raggedly euphoric power (costumed Lebowskis drunkenly belt out every word at fan conventions, and Jeff "The Dude" Bridges performs it live in his second career as a country singer). Dylan has rarely sounded as joyful as he does during the "la la la" intro, and gospel-tinged backup vocals add to the lyrics' sense of unguarded intimacy and deliverance in hard times.

Bob Dylan; 100 Best Songs

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83

“Nettie Moore” (2006)

"I just let the lyrics go, and … they seemed to have an ancient presence," Dylan told Rolling Stone in describing the writing of his primordially rootsy 2006 album, Modern Times. On "Nettie Moore," he spins lines from Marshall Pike and James Lord Piermont's 1857 song "Gentle Nettie Moore" and the folk traditional "Moonshiner" into one of his most personal songs ever; Dylan is the world-weary leader of a "cowboy band" longing for his lover back home to help him cope with sins, misinformation, unfinished business and bad-luck women. "I'd walk through a blazing fire, baby," he croons, "if I knew you was on the other side."

Bob Dylan; 100 Best Songs

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82

“One of Us Must Know (Sooner or Later)” (1966)

One of his surliest kiss-off songs ever: Dylan crafted this painstakingly over nine hours and 24 takes in Columbia's Studio A, shuffling between members of the Band and a squadron of Bringing It All Back Home session men before finally nailing it. Released as a single, it never charted, but its sneered contrition remains a brilliant balancing act, a mix of sympathy, condescension and palpable ache. "I told you as you clawed out my eyes/That I never really meant to do you any harm," he sings, stretching out the last syllable over a majestic piano-and-organ ascent that's one of Blonde on Blonde's most breathtaking moments.