The 42 Best Bob Dylan Songs

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The 42 Best Bob Dylan Songs

America’s most beloved musical poet is having a resurgence of cool. Between his recent Nobel Prize in Literature and his upcoming triple-album of classics, aptly entitled Triplicate, due on Friday, The Bard is cementing his place in the history of rock ‘n’ roll even more permanently.

After polling our writers, editors, freelancers, and interns, nearly 100 Dylan songs received votes. Tracing his beginnings as a folky troubadour in the style of Woody Guthrie to his career-defining burst into electric guitar-based rock to his mid-career mysticisms to his later experiments and covers, here is Paste’s version of the 42 best songs by Bob Dylan.

42. “Sweetheart Like You”
Bob Dylan  is nobody’s feminist, but with this lean ballad, he offers a truth about the challenges facing those pioneering women in the music business. Believed to be written about his ‘80s/’90s business associate Deborah Gold, the notion of “you could be known as the most beautiful woman to crawl across cut glass to make a deal” rings true for generations of women. And beyond the distaff side of “Sweetheart,” Dyland offers a couplet for ethos with the prescient pronouncement: “Steal a little and they throw you in jail/ Steal a lot and they make you king.” It’s a song that offers more truth to the reality of women in the workplace, as well as in love. —Holly Gleason

41. “I Dreamed I Saw St. Augustine”
Dylan hasn’t performed this John Wesley Harding track that often live, though it did land on the set list for his Rolling Thunder Revue tour and the one he undertook with Tom Petty and The Heartbreakers. And we shouldn’t fault him for that, as it is one of his most revealing and desperate songs. An homage to to the poem-turned-folk song “I Dreamed I Saw Joe Hill Last Night,” “Augustine” is a painful ballad, ripe with religious imagery that speaks to a deep well of guilt and sorrow that resides in Dylan’s heart. —Robert Ham

40. “My Back Pages”
Though Dylan wouldn’t excommunicate himself from the folk scene until he went electric at the 1965 Newport Folk Festival, “My Back Pages” was his public dismissal of his old identity as the de facto spokesman for the deeply entwined folk and protest movements, nearly a year before the fateful Newport set. At just 23 years old, Dylan was increasingly uncomfortable with being labeled the “voice of a generation” just by writing protest music and “My Back Pages”—off 1964’s Another Side of Bob Dylan—sees him tearing down the version of himself that wrote songs like “The Times They Are A-Changin’” and “Blowin’ in the Wind.” He decries the “lies that life was black and white” that were built on “romantic facts of Musketeers foundationed deep somehow.” He talks about being deceived into thinking “good and bad” could be defined “quite clear, no doubt, somehow” and becoming his enemy “in the instant that [he] preached.” It’s a harsh self-examination that single-handedly obliterates the first stage of Dylan’s career along with his biggest hits at the time. The effect of the song is made all the more potent by Dylan’s uncompromising, harsh wail that spits out the lyrics with a mixture of anger, sadness, and embarrassment. Though he denounces his old self-assurance, Dylan still sounds as confident as ever when he sings the refrain, one of his best and most concise lines ever: “I was so much older then, I’m younger than that now.” —Cameron Wade

39. “Stuck Inside Of Mobile With The Memphis Blues Again”
Dylan described his double album masterpiece Blonde on Blonde as, “The closest I ever got to the sound I hear in my mind … that thin, that wild mercury sound.” Opinion divides on the number: Hunter S. Thompson loved it and John Lennon hated it. The lyrics prowl around into Dali-esque hinterlands only to return with the yowling lament of certainty to conclude each stanza.

“Stuck” is Dylan at his lilting, incredulous best on this LP. It’s a ballad of ludicrous fancy and bedrock emotional truth. By the time of Blonde on Blonde, Dylan had mastered the ability to wring feeling from verses as nonsensical as Edward Lear or Spike Milligan. Here, he echoes the biblical prophets, arguably a major component in his influence. Nothing in the Book of Amos sounds like cut silk, and neither does Dylan. —Jason Rhode

38. “Absolutely Sweet Marie”
It’s little wonder that pub rock groups like the Flamin’ Groovies and Ducks Deluxe covered this track from Blonde On Blonde. That stomping beat from drummer Kenneth Buttrey is pure rock and roll, even if Dylan and co. spend the song pulling back the reins to keep the tempo at a nice even gallop. There’s a hard charging tension to it all, especially in the lyrics that speak symbolically of sexual frustration (“I got the fever down in my pockets / The Persian drunkard, he follows me”) and pleading romantic sentiments. Marie must have been someone quite special to elicit this kind of unabashed panting and moaning. —Robert Ham

37. “When I Paint My Masterpiece”
Levon Helm’s voice, like a nasal truth of Appalachia or Arkansas backwoods, offers the hope of old-time gospel and the celebration of knowing one will arrive when the Band recorded it on Cahoots. It remained largely a Dylan-for-The Band effort, in spite of various Dylan recordings trickling out. What matters beyond who recorded it (although it should be noted that Helm’s parched pine tone imbues it with a certain cracked glory) is the faith that one can realize their gifts, find their purpose and create something they were destined to make in spite of life’s struggle. Again, there are plenty of Biblical references and suggestions here, totaling to a song of commitment, fidelity, creativity and love. If Dylan has written a prayer for times of struggle, this may well be it. —Holly Gleason

36. “Rainy Day Women #12 & 35”
Among Dylan’s many lauded sing-a-longs “Rainy Day Women #12 & 35” hasn’t held up quite as well as the rest of Blonde on Blonde. It’s brash and bawdy, relying on an out-of-step brass band for orchestration, and even its lead singer giggles during the track’s most notorious line, “EVERYBODY MUST GET STONED!” Those words, plus other clues, like the fact that 12 times 35 equals 420, has caused bunch of listeners to write this one off as simply “a stoner song.” That could be, or it could be that the words “they’ll stone ya” take on a more ominous, biblical meaning. Dylan himself hasn’t ever clarified, but 50 years on, does it really matter anymore? —Rachel Brodsky

35. “Idiot Wind”
Has anyone ever come up with a more striking, original metaphor for stupidity? On one level, it brings to mind the insult “full of hot air,” as though Dylan’s subject has nothing valuable to say or contribute. Encouraging that interpretation are brutal punches like, “You’re an idiot, babe / It’s a wonder that you still know how to breathe.” But it’s also possible to read the character as more a victim than a villain; a casualty of an “idiot wind” that’s blowing around and eventually even infects Dylan himself (marked by the famous switch from “you” to “we” at the end). Every single image in this song is vivid, and every plotline is dramatic. The stakes of the story couldn’t be greater, and Dylan fully commits to them with a biting vocal delivery. He’s written a million diss songs, but this might be his best. —Monica Hunter-Hart

34. “Forever Young”
With The Band providing funky rock ‘n’ roll backup, Dylan delivered a fast and slow version of “Forever Young” on Planet Waves. A blessing for his sons that was derived in part from Book of Numbers in the bible, the oft-covered tune may have seemed an oversung cliché by Rod Stewart’s phlegmy take or Meatloaf’s bloated version, but Joan Baez’s purity, Pete Seeger’s 2012 grind and Johnny Cash offer the universal dignity Dylan intended. Still, it’s The Last Waltz’s elegiac version, accordion sighing, electric guitar slithering and the piano chords rising and falling, where Dylan’s performance coalesces. At The Band’s final concert, his performances embodies the hope, as well as the toil of life that yields an elegant beauty that urges, “embrace your youth no matter how old you are.” —Holly Gleason

33. “If You See Her, Say Hello”
It seems like 1975’s Blood on the Tracks encapsulates all seven stages of grief. While other album tracks on this list cover some of the other elements (“Simple Twist of Fate” is the initial shock and denial, “Idiot Wind” is the anger, etc.), “If You See Her, Say Hello” is surely the depression. The song details a breakup, with Dylan trying to sound like he’s doing okay in the aftermath of the “falling out.” But like most true loves, this anonymous lover sticks around in our narrator’s heart, as Dylan moans, “And though our separation / It pierced me to the heart / She still lives inside of me / We’ve never been apart.” Still, the beauty of “If You See Her, Say Hello” remains in the details. It’s worth a few listens to apprecaite the lyrical subtleties of the verses. —Hilary Saunders

32. “You’re Gonna Make Me Lonesome When You Go”
By Blood on the Tracks, Dylan had weathered the weight of being Bob Dylan, going electric, the disappearance post-motorcycle wreck, and enough star trappings to be warped by it all. “You’re Gonna Make Me Lonesome When You Go” sparkled as a vulnerable ballad that captured perfect love and yearning in a series of questions and images, embracing the inevitable and suggesting self-reflection in a way that was tempered with kindness. The song isn’t marked by large gestures, or cutting irony; rather, it’s a nod to the folk music that defined his origins. —Holly Gleason

31. “Not Dark Yet”
Dylan’s never been known as a particularly upbeat guy, but 1997’s Time Out of Mind is dark even by his standards, an impression that was magnified even more so at the time as Dylan had suffered a near-fatal heart infection just months before its release. “Not Dark Yet” is the album’s centerpiece, a beautifully sorrowful song centered around the refrain “It’s not dark yet, but it’s getting there.” Though the song was finished long before Dylan’s brush with death, the song, and others like it on the album, feels like Dylan finally hitting his breaking point. Not only has he lost his “sense of humanity,” unable to care about anything or to bear his own burden, but the world around him is also in tatters, “full of lies” and without even a “murmur of a prayer.” There is no salvation or savior in this world and it’s only getting worse. It is a relentlessly bleak song, not helped any by Dylan’s hard, nasally tone that, at this point, had begun corroding into what it is today (love it or hate it). Despite the subject matter, the song is so listenable thanks to bright guitars that give even Dylan’s most melancholic statements a sliver of hope. “Not Dark Yet” is as morose as Dylan has ever gotten, but it remains one of his best compositions both lyrically and musically. —Cameron Wade

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