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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.

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.

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.

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.

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.

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.

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.

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.

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.

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.”

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.

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.”

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.

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.

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.

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.

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.

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.

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.

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.”

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.

81. “Series of Dreams” (1991)

Dylan emerged from his worst artistic period to team up with Daniel Lanois for 1989’s creative comeback Oh Mercy. But in an unsurprisingly strange move, he dumped one of the best songs off the album. “Lanois liked the song,” Dylan wrote in his 2005 memoir, Chronicles. “He liked the bridge better, wanted the whole song to be like that. … It just couldn’t be done. … Thinking about the song this way wasn’t healthy.” Two years later, the tumbling track came out; true to its title, it’s a flow of fragmented images (“In one, the surface was frozen/In another I witnessed a crime”) delivered with a striking just-woke-up frankness.

80. “Someone’s Got a Hold of My Heart” (1991)

Dylan originally cut this tender tune for 1983’s Infidels, but axed it to make room for far weaker material, like “Union Sundown” and “Neighborhood Bully.” Later, he rerecorded it with producer Arthur Baker for 1985’s Empire Burlesque, complete with cheesy synths, intrusive backup singers, worse lyrics and a new title – “Tight Connection to My Heart (Has Anybody Seen My Love).” When the original version finally surfaced, fans had a chance to hear an exploration of spiritual ambivalence that perfectly reflected a moment in his career when he clearly wasn’t sure where he was going.

79. “Romance in Durango” (1976)

Scott Avett (of the Avett Brothers): When I was growing up, I was into hardcore music; my idol was Mike Patton from Faith No More. But when I was 21, an art-school professor gave me Desire. It was an awakening. It’s full of repetitive, almost poetic chanting from a man who’s seen a lot. Blood on the Tracks was intimate, but Desire was edgy. Dylan sounded like a hardened, mysterious figure. He was probably going through very normal changes in his life, but the way he would articulate them was so colorful. The melody of “Romance in Durango” makes the whole song work; it’s so serious and driven. And like most of Desireand Blood on the Tracks, it is relatively repetitive, but it’s so good it can kind of just keep going and going. That’s really much harder to do than I think anybody who isn’t trying to make music knows. As far as the lyrics go, it’s an amazing endeavor; Dylan was able to put his mind and heart into a specific scene – of being a lone renegade in the desert, up to all these trying and dangerous things. You’re buying all the masculinities and going right along with it. It’s convincing.

We got the chance to play “Maggie’s Farm” with Dylan at the Grammys a couple of years ago, and I couldn’t stop smiling. He was superpolite and very straightforward throughout rehearsals; there were no games. Donnie Herron, from Dylan’s band, is a friend of ours, and he says that Dylan plays all day long on his bus and knows so many songs – people have no idea. He’s just wiser and much further along in his journey, so we look up to him. I think we’re comrades in a way. I really believe that.

78. “Absolutely Sweet Marie” (1966)

“To live outside the law you must be honest,” Dylan sang, dropping one of his most quoted lines on Blonde on Blonde‘s spriest pop tune. “Absolutely Sweet Marie” is a cryptic love letter that rides a bubblegum electric keyboard and sparkling blues-rock guitar. Dylan waited more than 20 years to play it live, but the song stands high among Dylan covers; garage-punk progenitors the Flamin’ Groovies and alt-country forebears Jason and the Scorchers have both testified to its rock & roll soul. Looking back at it on its 25th anniversary in 1991, Dylan patted himself on the back: “It’s matured well,” he said. “It’s like old wine.”

77. “Tonight I’ll Be Staying Here With You” (1969)

“I was on the road for almost five years. It wore me down. I was on drugs, a lot of things. … I don’t want to live that way anymore,” Dylan told Rolling Stone‘s Jann Wenner in 1969. He sounds content to settle down into domestic bliss on Nashville Skyline’s laid-back closing track (a close cousin to John Wesley Harding‘s “I’ll Be Your Baby Tonight”), showcasing his smooth country croon between twangy guitar fills. A more raucous version became a live highlight a few years later during the Rolling Thunder Revue, and Dylan still plays it early in shows on his Never Ending Tour.

76. “Gates of Eden” (1965)

“This is called ‘a sacrilegious lullaby in D minor,'” Dylan joked to his audience on Halloween 1964 at New York’s Philharmonic Hall. Written in the early summer and recorded in one take the following winter, the acoustic B side to “Like a Rolling Stone” features some of his spookiest imagery ever – the savage soldier, the motorcycle-black Madonna, the gray-flannel dwarf – all destined for the Gates of Eden, which turns out to be no paradise at all, but a place of deafening silence, with no kings, trials or sins. It’s an anthem against the notion of heavenly redemption: “Lotta people wait until they’re at the end of the line,” Dylan said years later. “You don’t have to wait that long. Salvation begins right now, today.”

75. “Sweetheart Like You” (1983)

It’s misogynistic (“a woman like you should be at home”); its lyrics are at times an incomprehensible mixture of romantic and religious imagery (“They say in your father’s house, there’s many mansions/Each one of them got a fireproof floor”). But this closing-time benediction undercuts all that with an unmistakable tenderness. Many Dylan scholars see the song as a farewell to his Christian phase, interpreting the chorus, “What’s a sweetheart like you doing in a dump like this?” as a metaphor for Jesus being maligned by the corrupt religious establishment. If so, it’s an oddly touching goodbye.

74. “All I Really Want to Do” (1964)

1964’s “The Times They Are A-Changin'” got the upstart Dylan tagged the angry voice of a rebellious, socially conscious generation. So, true to chameleon form, he opened his next album with a bit of lighthearted flirtiness that’s also a sly shot at the then-burgeoning cult of male sensitivity. He piles up an absurd list of things he won’t do (“fight with you,” “tighten you,” “drain you down,” “bring you down”) en route to winning a woman’s friendship. His Jimmie Rodgers yodel and sneaky fit of midsong laughter gives the tune an anything-goes sense of optimism expanded by the Byrds’ wide-open electric version from 1965.

73. “I’m Not There” (2007)

Recorded with the Band during the Basement Tapes sessions in 1967, “I’m Not There” was the stuff of bootleg lore for decades, finally seeing the light of day in 2007 on the soundtrack to the Dylan biopic that shares its name. The track’s clipped opening shaves off the first few seconds to give the impression of walking in on a private moment. The lyrics heighten that sense by seeming to describe an abandonment in terms that only make sense to the singer himself. With desperate vocals from Dylan and amazing organ work by Garth Hudson, “I’m Not There” is the only song from the Basement Tapes sessions with the “thin, wild mercury” sound of Blonde on Blonde. The results are absolutely haunting.

72. “Rainy Day Women #12 & 35” (1966)

The closest thing Dylan ever recorded to a party anthem had the working title of “A Long Haired Mule and a Porkepine.” Dylan ended up giving it a name rooted in one of his sideways biblical allusions (to a line from Proverbs, “a continual dropping in a very rainy day and a contentious woman are alike”), underscoring the joke in the lyrics that “they’ll stone you” for sins; producer Bob Johnston’s idea to record the song “Salvation Army-style” added to the religious undercurrent. One of the half-dozen songs cut in the marathon 13-hour session that completed Blonde on Blonde, it became a Number Two hit.

71. “Most Likely You Go Your Way and I’ll Go Mine” (1966)

This might’ve been a much less dynamic rocker had bassist Charlie McCoy not picked up a trumpet and asked to play along with Dylan’s harmonica riff. Dylan declined, because he hated overdubs. “[Charlie] said … ‘I can play the bass and the trumpet at the same time,'” keyboardist Al Kooper recalled. “Our jaws hit the ground.” Dylan thought the stunt might distract him while singing, so he ordered McCoy to play behind a curtain. The trumpet ended up adding a funky energy to one of Dylan’s bitter send-offs.

70. “To Ramona” (1964)

Jackson Browne: There’s not a word about the Civil Rights movement in this song. But to me, it’s about that as clearly as a James Baldwin novel. I’ve always seen Ramona as a young black woman at some New York party where she doesn’t feel comfortable, and there is Bob Dylan giving her emotional contact. He’s specific about the erotic, her attractions. I see that woman’s beautiful black face, her “cracked country lips.” He’s describing her in terms that take us past this scene.

It is a song imbued with the struggle for personal freedom and the perpetual trap of co-dependence. This was a moment when people wanted a leader and spokesman. But in this song, Dylan dismantles that: “I’d forever talk to you/But soon my words/They would turn into a meaningless ring.” He’s always an advocate for finding your own way.

The problem with any kind of polemic is that it’s too rigid for what life really is. That is at the heart of Bob Dylan’s elusiveness. He tells Ramona, “You’ve been fooled into thinking/That the finishin’ end is at hand.” But it’s not. These battles will go on.

69. “One More Cup of Coffee (Valley Below)” (1976)

On May 24th, 1975 (his 34th birthday), Dylan was visiting painter David Oppenheim in the South of France, and the two of them went to a gypsy festival. There, as Dylan later recounted, he “got mixed up with someone” and met a man who “had maybe 16 to 20 wives and over a hundred children.” Dylan stayed for a week; as he left, he asked for a cup of coffee for the road. “I wasn’t sure if I could say anything else, but it was dangerous territory,” he claimed. That’s a good story, anyway, and it might have been the germ of “One More Cup of Coffee.” The song is an eerie-sounding tribute to a woman with eyes “like two jewels in the sky” and a rich and powerful father. It’s full of mysticism and made all the more powerful by the distinct vocals: Dylan’s keening voice blends with spooked-angel backing from Emmylou Harris. The real gypsy gesture here, though, is Scarlet Rivera’s haunting violin line.

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.

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.”

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.

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.

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.

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.

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.”

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.

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.

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.”

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.

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.

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.

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.

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.

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.

52. “Tears of Rage” (1975)

This mesmerising 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 agonising 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.

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’.”

50. “Not Dark Yet” (1997)

A few months before Dylan released 1997’s Time Out of Mind, he was hospitalised with a severe heart infection that made him believe that he’d “be seeing Elvis soon.” “Not Dark Yet” was finished long before this illness had set in, but the hauntingly beautiful song seemed to almost foretell it. Against Daniel Lanois’ trademark swampy production, Dylan sings in the weary and weathered voice of a man facing the twilight of his life. “I was born here and I’ll die here against my will,” he sings. “I know it looks like I’m moving, but I’m standing still.” Dylan had been recording death-obsessed songs since his very first album in 1962. Here, he was a road-weary 55, in the middle of his Never Ending Tour, and you can hear every one of those years in that voice.

49. “Up to Me” (1985)

“Up to Me” is one of the top-shelf songs that Dylan left off albums (in this case, Blood on the Tracks) for reasons known only to the man himself. It is reminiscent of “Shelter From the Storm,” both musically and in terms of its spare arrangement. Thematically, the song would have perfectly suited Blood on the Tracks, which was inspired by the dissolution of Dylan’s marriage to Sara Lownds. It’s possible that “Up to Me” was simply too personal for Dylan to release at the time. “And if we never meet again, baby, remember me,” he sings in the song’s last verse. “How my lone guitar played sweet for you that old-time melody.” Of course, he denied that interpretation. “I don’t think of myself as Bob Dylan,” he told Cameron Crowe. “It’s like Rimbaud said, ‘I is another.'”

48. “Sara” (1976)

The most overtly autobiographical song Dylan ever wrote directly addresses his then-estranged wife. It also showed that Dylan could turn on the charm. “Sara” is a love song largely devoted to memories – images of their children at play, the couple sharing glances over “white rum in a Portugal bar” – with Dylan referring to Sara as the “sweet love of my life” in a spare, dirgelike waltz. Late in the song, Dylan pointedly asked for forgiveness but also sounded like a man grown distant and mystified, referring to Sara as a “Scorpio Sphinx in a calico dress.” The Dylans reconciled for a time, but as the marriage disintegrated for good the next year, Dylan replaced “Sara” with the splenetic “Idiot Wind” in the Rolling Thunder Revue’s sets. The pair were officially divorced in 1977.

47. “Spanish Harlem Incident” (1964)

Dylan performed this brief, tender slip of a song about a crush on a fortune teller exactly once. The “incident” of its title seems to be as tiny as incidents come: the “gypsy gal” holding his hand in hers, and sparking a flurry of associations. “Spanish Harlem Incident” is one of Dylan’s most open, unambiguous sex songs, complete with references to her “rattling drums” and his “restless palms.”

46. “Jokerman” (1983)

Chris Martin: I got into Bob Dylan when I was 16. I’d heard the myth, “Oh, Bob Dylan, he can’t sing.” But at this point, half the CDs I own are Dylan albums. About once a year, I’ll spend a month listening to Dylan and nothing else.

I discovered Infidels after I saw the video for “Jokerman.” It had Italian paintings and religious imagery. I’d thought I was a massive Dylan fan, but “Jokerman” was a shock: “How can this guy have a song that comes from this other world, and it’s still so brilliant?” Mark Knopfler and Mick Taylor on guitars. And Sly and Robbie brought that reggae vibe. The song feels 87 minutes long, like dinner finally came around and they stopped rolling tape. I spend eight weeks writing two lines.

I don’t think about who this Jokerman is – whether it’s God, Satan or Dylan himself. The beauty is in the mystery. I love the lines “The book of Leviticus and Deuteronomy/The law of the jungle and the sea are your only teachers.” And the chorus, with that “oh-oh-oh” chant out of tune – the only other person who can get away with singing like that is Jay Z, on “D.O.A.” It sounds effortless in the best possible way.

45. “It Ain’t Me, Babe” (1964)

Likely written in a London hotel, “It Ain’t Me, Babe” is among Dylan’s most elegant women-don’t-get-me songs, cataloging an erstwhile girlfriend’s ill-founded expectations of old-fashioned chivalry and fidelity. The opening line (“Go ‘way from my window”) is a poetic formula that goes back to the 16th century, but the song also takes from more contemporary sources: The “no, no, no” appeared to parody the “yeah, yeah, yeah” in the Beatles’ “She Loves You.” “Eight in the Top 10,” Dylan said of the Fab Four’s pop dominance. “It seemed to me like a definite line was being drawn.”

44. “Stuck Inside of Mobile With the Memphis Blues Again” (1966)

“Oh, mama, can this really be the end?” Dylan moans over and over in this desperate seven-minute epic. Dylan drives the Nashville session pros through verse after verse of surreal blues imagery, and the band sounds inspired by the challenge. The mood is all sex, drugs, temptation and paranoia. Despite the poetic abstraction, Dylan delivers one of Blonde on Blonde‘s most sensual vocals.

43. “Gotta Serve Somebody” (1979)

Sinéad O’Connor: I was about 13 when my older brother Joseph brought home Slow Train Coming, and it just completely blew my mind. People say – and I hope it’s not true – that Dylan doesn’t stand by that record. It’s a staggering album for anyone to make, but especially him.

The song that killed me most was “Gotta Serve Somebody.” Living in a Catholic family in Ireland, the only religious music we had ever heard was just awful – so incredibly boring. For that song to come out in Ireland at that time was life-changing. He wasn’t giving a lecture. There was a sexuality, almost, in the sound of the guitar and the other instruments.

And the lyrics are brilliant – what he’s saying is that whatever you’re going to do with your life, you’re fucked if you don’t stand for something. I quite like that, as a lesson from a master teacher on how to be an artist and also, I suppose, on how to live your life. What he’s saying is, “Don’t just get into your bed and curl up under the covers. You have to get the fuck up.”

42. “I Threw It All Away” (1969)

After seven years of Dylan songs that were wildly original, it was a shock to hear him plunge into straightforward Tin Pan Alley-style song structure, and even more of a shock to hear his hyper-articulate cowboy mouth murmuring lines like “Love is all there is, it makes the world go ’round.” Turns out he was great at straight-faced country rock, too: The song’s regretful lyrics suggest that it is an apologia for the sharp left turn Dylan’s career had taken, from the hard-touring, reluctant pop oracle to a clean-cut homebody who longed to be a part of the Nashville machine.

41. “I’ll Keep It With Mine” (1985)

Dylan cut “I’ll Keep It With Mine” in 1965 but didn’t release it until years later – and has never played it live. That didn’t stop others from falling in love with the song, a ballad of friendship whose 1965 version features a sweet, plaintive vocal. “It’s hypnotic – just Dylan and piano,” says Cameron Crowe, “and his vocal is kind of heroic.” (The song has been covered by Judy Collins, Nico and Fairport Convention.) “Maybe it didn’t sound like a record to me,” said Dylan, talking about shelved recordings like “I’ll Keep It With Mine.” But he was still philosophical about this particular song’s appeal: “If people like it, they like it.”

40. “I Dreamed I Saw St. Augustine” (1967)

This deliciously ambiguous hymn riffs on the opening line of “Joe Hill,” a folk standard about a labor organizer and songwriter who was executed (and probably framed) for a double murder. Dylan replaces folkie certainty with layered complexity: St. Augustine is a martyr, but the narrator places himself “amongst the ones/That put him out to death,” and it’s never clear if we should sympathize with Augustine or Dylan or anyone at all. What we do know for sure is Dylan’s tattered, slightly out-of-tune intensity. It’s an earnest gesture of faith in something that he doesn’t quite understand.

39. “Hurricane” (1976)

In 1975, Dylan took up the cause of Rubin “Hurricane” Carter, a black boxer serving a life sentence for a 1966 triple murder. “I recognised the fact that here was a brother,” Carter said of Dylan, who visited him in jail. Dylan would organize two benefit concerts, and with theater director Jacques Levy, he wrote “Hurricane,” a roaring declaration of the boxer’s innocence. The song opens like a film script (“Pistol shots ring out in the barroom night”), and ends more than eight minutes later with Carter in jail. The attention Dylan called to Carter helped win him a retrial, but he was convicted again. Then, in 1985, that conviction was overturned. In 1988, all murder charges against him were dropped.

38. “My Back Pages” (1964)

“My Back Pages” was the sound of the greatest protest singer of the Sixties leaving politics behind – an alternately wistful and sneering ballad in which Dylan recalls his days as a political folkie and pokes fun at his former self-seriousness on the song’s chorus: “I was so much older then, I’m younger than that now.” Dylan promised a break with the past by calling the LP Another Side of Bob Dylan. “My Back Pages” was his statement of intent. “There aren’t any fingerpointing songs here,” Dylan said of the album. “I don’t want to write for people anymore. You know – be a spokesman.”

37. “Maggie’s Farm” (1965)

The song that announced a reborn Dylan, when he opened his debut electric set with it at the 1965 Newport Folk Festival, was in fact a folk song: a riff on the evil boss-man tune “Down on Penny’s Farm.” In its studio version, “Maggie” was a swinging country rocker, but the Newport take wasn’t so jolly. Over lacerating guitar, Dylan declared, “I try my best/To be just like I am/But everybody wants you/To be just like them.” His defiant tone later inspired Barack Obama, who cranked the song to steel himself during the 2008 election. “I’ve got probably 30 Dylan songs on my iPod,” he told Rolling Stone. “One of my favorites during the political season is ‘Maggie’s Farm.'”

36. “With God on Our Side” (1964)

Tom Morello: I may be the last person alive who still believes that Dylan sold out at Newport in 1965 when he went electric. The pressure was on to lead a movement, something he didn’t sign up for and wasn’t interested in. I think he missed an opportunity to see if there was a ceiling to what music could do to push forward radical politics. But he came close with “With God on Our Side.”

I never knew how politically radical Dylan was until I got The Times They Are A-Changin’. He was 22 but sounds like he’s 80, like this wizened guy who’s had a long life as a vigilante, croaking out songs of hard truth. But “With God on Our Side” is not some historical relic. It is a living exposé of war crimes, past, present and future. Dylan lays bare the hypocrisy of war and unmasks the whitewashing of our military ventures. He’s singing about the people who make war, profit by it, and the families that send children to die. “You don’t count the dead when God’s on your side,” he sings. “And you never ask questions when God’s on your side.” From shock-and-awe to Abu Ghraib to the morass in Afghanistan, those phrases can very much be applied to our exploits today.

35. “The Lonesome Death of Hattie Carroll” (1964)

“It’s a true story, but I changed the reporter’s view,” Dylan said of this chilling murder ballad. Dylan had read a story in Broadside, his favorite folk-music zine, about Hattie Carroll, a black hotel employee and a mother of nine from Baltimore, who died after she was allegedly struck by William Zantzinger, a white tobacco-farm owner. Zantzinger subsequently served six months in jail for manslaughter, though evidence later cast doubt on his guilt. Zantzinger is certainly guilty in “The Lonesome Death of Hattie Carroll,” a deceptively gentle-sounding song, in which Dylan tweaked some of the facts of the case while keeping the details thick and vivid (the murder weapon is “a cane that he twirled around his diamond ring finger”). The result was a compelling story-song that doubled as an indictment of racism and class division. “The pacing is punctuated by that lovely, lilting chorus,” says Tom Morello. “It feels like you’re walking toward her grave.”

34. “Isis” (1976)

Sara Dylan was in the studio the day her husband recorded “Isis.” Her presence was fitting: The song may well be an elaborate allegory of their marriage, separation and brief reunion – reimagined as the epic quest of a narrator who must trek through icy storms, scale pyramids and rob an ancient grave before winning back his runaway bride, the “mystical child” named Isis. Dylan wrote much of it in an all-night session with theater director Jacques Levy. He was so proud of the lyrics that he presented them to friends at the New York club the Other End. “Bob read the lyrics to a bunch of people sitting around the bar, and everybody responded,” said Levy. “Everyone gets hooked in that story.” Before long, an incendiary version of “Isis” became a mainstay of Dylan’s Rolling Thunder Revue. With his face painted white, Dylan would stalk the stage like a shaman, using only his voice, harmonica, hands and body to illustrate the song’s tall tale. It was the first time most fans had ever seen him perform in concert without a guitar.

33. “Idiot Wind” (1975)

The original version of this Blood on the Tracks centrepiece was a rueful acoustic ballad, but when Dylan rerecorded half of the album at the last minute in Minneapolis, the heavily rewritten “Idiot Wind” became one of his most scathing, frothing, furious songs – a rant against the woman he married and idiocy itself. “You’re an idiot, babe/It’s a wonder that you still know how to breathe,” goes the chorus, and that’s not even as harsh as it gets. Dylan makes sure he’s not spared from blame: “It’s a wonder we can even feed ourselves,” he sings in the last line. The live version on Hard Rain – performed with its apparent target, his soon-to-be ex-wife, in the audience – is crueler and even more gloriously raging. Dylan said of the song, “I didn’t feel that one was too personal, but I felt it seemed too personal. Which might be the same thing.”

32. “Chimes of Freedom” (1964)

The most ambitious song Dylan had written to date – a six-verse masterpiece in which a thunderstorm and its lightning flashes become a beacon that summons outlaws, outcasts, artists and “every hung-up person in the whole wide universe” – reportedly evolved out of a brief poem he’d written about John F. Kennedy’s assassination in late 1963. Dylan’s gift for internal rhyme and assonance flowered here, as did his knack for phrasemaking: “starry-eyed an’ laughing,” “midnight’s broken toll,” “chained an’ cheated by pursuit.” He first performed it in mid-February 1964, and recorded it that June for Another Side of Bob Dylan(after half a dozen false starts – it’s tough to keep that many lines straight). By the end of the year, he’d dropped “Chimes of Freedom” from his set, but other artists picked it up and ran: The Byrds recorded it for their first album in 1965, and Bruce Springsteen made it the title track of a 1988 EP.

31. “Can You Please Crawl Out Your Window?” (1965)

Dylan famously kicked folk singer Phil Ochs out of a limousine for saying he didn’t like “Can You Please Crawl Out Your Window?” In fact, it’s one of Dylan’s great diss tracks. A sequel of sorts to “Like a Rolling Stone,” the song distills its predecessor’s torrent of contempt down to a taut three and a half minutes of lean, tossed-off spite. The driving, no-frills style came courtesy of Levon and the Hawks, who were backing Dylan in the studio for the first time after playing only a handful of live shows with him. But like Ochs, the public wasn’t buying it: “Can You Please Crawl Out Your Window?” fizzled at Number 58 on theBillboard charts.

30. “Girl From the North Country” (1963)

Keith Richards: While the British Invasion was going on, Bob Dylan was the man who really pulled the American point of view back into focus. At the same time, he had been drawing on Anglo-Celtic folk songs, and that’s certainly true of “Girl From the North Country.” It’s got all the elements of beautiful folk writing without being pretentious.

In the lyrics and the melody, there is an absence of Bob’s later cutting edge. There’s none of that resentment. He recorded it again later with Johnny Cash, but I don’t think it’s a duo song. Bob got it right the first time.

In a way, I see “Girl From the North Country,” “Boots of Spanish Leather” and “To Ramona” as a trilogy. Is Ramona the girl from the north country? Is she the same chick who sends the boots of Spanish leather? There’s some connection between them. Also, the guitar picking is almost the same lick in “Boots of Spanish Leather” and “Girl From the North Country.” It’s like an extension of the same song.

Before he went electric and submitted himself to the discipline of a rhythm section, there was a beautiful flow in Bob’s songs that you only get with just a voice and a guitar. He can float across a bar or let certain notes hang, and it doesn’t matter because it all goes with the song.

He’s the most prolific writer: I think he’s written more songs than I’ve had hot dinners. So, Bob, just keep ’em coming! He’s an inspiration to us all, because he’s always trying to go somewhere new. I love the man – and I love that he rock & rolls too!

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.

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.”

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.

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.”

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.

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 colour. 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.

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.”

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.”

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.

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.”

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.”

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.'”

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.

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.

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.

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 (phoney 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.”

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.

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.

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.

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.”

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.”

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.

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 phoney 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.”

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.”

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.

4. “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.”

3. “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.

2. “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.”

1. “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.

In This Article: Bob Dylan