100 Greatest Bob Dylan Songs

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.

“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.

“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.

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.

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.

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.

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.

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.”

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.

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.”

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.

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.

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.

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.

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.

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.

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.

“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.”

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.

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.

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.

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 Desire and 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.

“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.”

“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.

“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.”

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.

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.

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.

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.

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.

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.

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.

“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.

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.”

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.

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.

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.