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100 Greatest Bob Dylan Songs

From “Just Like a Woman” to “John Wesley Harding,” we count down the American icon’s key masterpieces

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As Bob Dylan turns 75, he shows no signs of slowing down. The American icon is gearing up for a summer tour with longtime friend Mavis Staples and has just released Fallen Angels, his 37th LP and second straight Sinatra-inspired album of American Songbook classics. For generations to come, other artists will be turning to Dylan’s own catalog for inspiration. From the Sixties protest anthems that made him a star through to his noirish Nineties masterpieces and beyond, no other contemporary songwriter has produced such a vast and profound body of work: songs that feel at once awesomely ancient and fiercely modern. Here, with commentary from Bono, Mick Jagger, Lenny Kravitz, Lucinda Williams, Sheryl Crow and other famous fans, are Dylan’s 100 greatest songs – just the tip of the iceberg for an artist of his stature.

Bob Dylan; 100 Best Songs

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50

“Not Dark Yet” (1997)

A few months before Dylan released 1997's Time Out of Mind, he was hospitalized 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.

Bob Dylan; 100 Best Songs

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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.'"

Bob Dylan; 100 Best Songs

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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.

Bob Dylan; 100 Best Songs

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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."

Bob Dylan; 100 Best Songs

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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.

Bob Dylan; 100 Best Songs

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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."

Bob Dylan; 100 Best Songs

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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.

Bob Dylan; 100 Best Songs

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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."

Bob Dylan; 100 Best Songs

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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 hyperarticulate 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.

Bob Dylan; 100 Best Songs

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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."

Bob Dylan; 100 Best Songs

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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.

Bob Dylan; 100 Best Songs

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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 recognized 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.

Bob Dylan; 100 Best Songs

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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."

Bob Dylan; 100 Best Songs

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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.'"

Bob Dylan; 100 Best Songs

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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.

Bob Dylan; 100 Best Songs

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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."

Bob Dylan; 100 Best Songs

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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.

Bob Dylan; 100 Best Songs

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33

“Idiot Wind” (1975)

The original version of this Blood on the Tracks centerpiece 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."

Bob Dylan; 100 Best Songs

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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.