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

30. “Lonesome Death of Hattie Carroll”

In 1963, a 51-year-old black barmaid named Hattie Carroll was fatally assaulted by a white man who complained that she’d been too slow to bring his drink. Her attacker was given only a six-month jail sentence. “The Lonesome Death of Hattie Carroll” narrates these events, and is probably one of Dylan’s most effective protest songs because it’s helped raise awareness of them for more than 50 years. At the end of each verse, he scorns aloof observers who “philosophize disgrace” and says that it’s not yet time to cry because the story gets worse. When he finally describes the court ruling and alludes to the threat of racism not just from individuals, but also institutions, he finishes, “Now’s the time for your tears.” —Monica Hunter-Hart

29. “With God on Our Side”

I first heard this song as the closing track on Bob Dylan’s 1995 MTV Unplugged release. As a teenager clutching a copy Highway 61 Revisted, I wasn’t sure where in The Bard’s massive cannon to dig next. Luckily a bargin bin copy of this LP caught my eye and poorly stuffed wallet, with its strange piano-laden version of this nearly eight minute dirge. Dylan traces every major violent conflict in America’s history, justifying each with a couplet like, “For you don’t count the dead / When God’s on your side.” But as he gets closer and closer to the modern day, he starts turing that phrase on itself, asking who’s side God is on, if anyone’s at all. By the final verse, Dyland delivers the prophecy that resonates today, even 50 years past it’s creation: “If God’s on our side / he’ll stop the next war.” —Hilary Saunders

28. “Mississippi”

Perhaps the most well loved song from Dylan’s late-stage comeback, “Mississippi” is Dylan doing what he does best. Buoyed along by a newly embraced country sound and one of the catchiest melodies he’s ever written, “Mississippi” harkens back to classic Dylan and folk music subjects: long lost loves, traveling across the wide-open country, and the mythic figure of the drifter. Each line sounds like a folk saying or country proverb that Dylan must have picked up over the decades crisscrossing America. On its surface, it’s a song about life breaking you down, returning to your roots, and finding love again, containing some of Dylan’s most romantic lyrics ever: “All my powers of expression and thoughts so sublime / could never do you justice in reason or rhyme.” But, like nearly every great Dylan song, there’s much more working underneath the surface. According to Dylan, the song has to do with “the Declaration of Independence, the Constitution and the Bill of Rights,” and some have read it as an allegory for the South and America’s history of slavery and racism. “Mississippi” is one of Dylan’s catchiest modern tunes that can still stand amongst his greatest works. —Cameron Wade

27. “Hurricane”

Before viral news and social media had the ability to fan the flames of protest, there were far fewer ways to rally crowds behind the injustices of racial profiling. But Bob Dylan did exactly this in 1975 with his urgent single “Hurricane,” which tells the story of Rubin “Hurricane” Carter, a middleweight boxer wrongly accused of murder in the mid-’60s. Against weeping strings, Dylan recounts a shooting in a Paterson, N.J. bar where five people were killed and Carter was wrongly implicated. “The trial was a pig-circus, he never had a chance,” he sings of the fallout, wisely pointing out how racial stereotypes affect the judicial system (“To the white folks who watched he was a revolutionary bum / And to the black folks he was just a crazy n***a”). The song, inspired by Carter’s earlier memoir, The Sixteenth Round, helped shine a light on the wrongful conviction, with the boxer eventually being freed ten years later. It would be nice to think that we’ve learned since then—that racial profiling and police brutality is no longer an issue. But we have a long way left to go. Fortunately, “Hurricane” will always be there to guide us forward. —Rachel Brodsky

26. “Tombstone Blues”

While Highway 61 is the route the delta blues took to travel north, Highway 61 is Bob Dylan’s path to the stratosphere. It’s the logical next step after Bringing It All Back Home, expanding upon the electric sounds he played with on that record. But—more importantly—it’s Dylan in top form, perhaps the first time he truly successfully paired his unparalleled lyricism with that rock ‘n’ roll music the kids were getting into. For evidence of that, look no further than “Tombstone Blues,” full of dynamite lines like “dropping a barbell, he points to the sky, saying ‘the sun’s not yellow, it’s chicken’” and a driving groove that threatens to fly off the rails at any moment. —Bonnie Stiernberg

25. “Highway 61 Revisited”

In addition to the musical legend of Highway 61, there’s also a biblical notion to these scenes that play out on the highway that runs from Minnesota to New Orleans.
“Highway 61 Revisted” captures them in many ways, and they’re just as resonant now—just apply the metaphors to current events. But with or without deeper meaning, this song rocks. And whether it’s a garage rock shakedown or a term paper analysis that you’re after, we can all listen to this and say, “amen.” —Holly Gleason

24. “Buckets of Rain”

The final sentiments on Blood on the Tracks, “Buckets of Rain” is the consummate rainy day blues song. It’s the final chapter of Dylan’s famed breakup record, and a one that slips into somber acceptance of said heartbreak. Like with so many of Dylan’s songs, the crushing blow comes in the form of the last verse. Here, he croons in his creaking voice, “Life is sad, life is a bust / All you can do is do what you must.” —Hilary Saunders

23. “Ballad of a Thin Man”

This Bob Dylan’s most brutal take down. Whether or not it was inspired by anyone in particular, it ends up a no-bars-held assault from Dylan’s razor sharp lyrical dagger that leaves all of the Mr. Joneses in his world bleeding out on the ground. He mocks (“Nobody has any respect / Anyway they already expect you / To just give a check / To tax-deductible charity organizations”), he sneers (“You’ve been through all of / F. Scott Fitzgerald’s books / You’re very well read / It’s well known”), and he spits (“Something is happening here and you don’t know what it is”) until he’s satisfied. When you add in the musi—that drunken vaudevillian piano and those whirling organ lines, in particular—it ranks among the most vicious songs on one of Dylan’s best albums. —Carter Shelter

22. “Maggie’s Farm”

No matter what machine Dylan is raging at, he’s definitely raging against the machine in “Maggie’s Farm” (which, of course, is fitting since Rage offered their own vicious cover on their 2000 covers album Renegades). It’s been said Dylan was fighting the Man, the service industry, the music industry, the military institution or even the previous iterations and perceptions of his persona. Regardless, “Maggie’s Farm” is the embodiment of inscrutability and has since been integrated into the pop cultural lexicon of defiance. —Hilary Saunders

21. “I Shall Be Released”

As great as Music From Big Pink is, I could never quite get behind The Band’s version of this song, which was the first version officially released. Something about Richard Manuel’s falsetto vocals taking the lead has always kept me at a distance. But even in that recording, and especially in Dylan’s Bootleg Series version, you hear the beautiful simplicity of the song’s construction matched with the depth of its meaning. It’s no surprise that countless artists, from Nina Simone to Wilco to Coheed and Cambria, have taken this song on (for better and for worse). On the surface, it’s a timeless gospel song that happened to come to the mind of Bob Dylan before it came to anyone else. But in the lyrics’ raw desperation and isolation wrapped in spirituality, it also explores the psyche of Dylan as he moved from prophet to troubadour. —Carter Shelter

20. “It’s Alright Ma (I’m Only Bleeding)”

This song holds some of Dylan’s most memorable lines, including the oft-quoted “He not busy being born is busy dying.” It’s metaphor upon metaphor of societal critiques, some vague and others direct (“money doesn’t talk, it swears”), but always intense. His words pour forth in bitter, unbroken surges that can hypnotize a listener into jadedness. Dylan doesn’t just expose the world’s darkness here; he reveals the ubiquity of that darkness. He brushes off absurdity and pain (“it’s alright”) because it’s normal. “You feel to moan, but unlike before, you discover that you’d just be one more person crying.” —Monica Hunter-Hart

19. “Boots of Spanish Leather”

Tucked in the middle of the very political The Times They Are A-Changin’ is “Boots of Spanish Leather,” a ballad told as dialogue between a woman traveling to Spain and the man she’s leaving at home. In just four-and-a-half minutes, Dylan creates two richly layered and dynamic characters, each reckoning with the messy emotions of young love coming to an end. The raw honesty at the heart of the song is pulled from Dylan’s own love life as his girlfriend at the time, Suze Rotolo (seen on the cover of his previous album), had left to study abroad in Italy during a particularly troubled time in their relationship. The final verse, where the man grimly accepts that his relationship is over, strikes deep thanks to Dylan’s soft guitar picking and quiet, hard-edged voice. “Boots of Spanish Leather” is Dylan at his most open and vulnerable—a rare sight for the notoriously introverted and private songwriter, but it proves he’s master of his craft, writing a heartbreaking ballad that measures up to the best of them. —Cameron Wade

18. “Knockin’ on Heaven’s Door”

One of Bob Dylan’s most immediately recognizable characteristics is his ability to imbue songs with a story — and not simply a story, but a profoundly moving one. On catalog staple “Knockin’ On Heaven’s Door,” which first appeared on the 1973 soundtrack of the film Pat Garrett and Billy the Kid, the troubadour-wordsmith projects an image of a dying sheriff begging his wife to remove his badge, because he “can’t use it anymore.” Death is hardly a groundbreaking subject to address in art, but “Knockin’ On Heaven’s Door” instead addresses the space between living and dying, that point where you know it’s the end. Your vision is darkening, the “black cloud is comin’ down.” There’s nothing left to do but to lay your weapon down and pray that the pearly gates will be there when you arrive on the other side. —Rachel Brodsky

17. “Simple Twist of Fate”

When meeting a potential soulmate, we love to call it fate. The shared spark, the feeling that somebody can know you with just one look—surely it’s more than mere coincidence! But what happens when it does not work out? “Simple Twist of Fate” tells of a scenario where it was not meant to be, yet instead of turning cynical, the narrator says to “blame it on a simple twist of fate.” This song exemplifies why Dylan is known as a songwriter who seems to transcend a human understanding of events; despite things not working out, his writing demonstrates a peaceful acceptance that comes from wisdom. —Jaimie Cranford

16. “Just Like a Woman”

Reputedly inspired by ultimate Andy Warhol superstar Edie Sedgewick—spider monkey thin, all kohl eyeliner, platinum hair and trust fund money—Blonde on Blonde’s “Just Like A Woman” comes on like a lurching seaman, cataloguing the reality of an entirely too fragile girl who captivates and then capsizes. Dylan’s wheezy rasp, delivered in between bouts of harmonica blowing, has been considered a tool of aggressive misogyny, defensive repudiation of responsibility for her condition. Growing up, the heroine seemed about the most exotic Glamazon of them all, and the romance of the good things far outstripped the much citedderision for “her fog, her amphetamines and her pearls.” —Holly Gleason

15. “It Ain’t Me, Babe”

“It Ain’t Me, Babe” is a sentiment that so many will never admit to themselves, and yet, it’s right there in the title. In its three short verses, Dylan’s able to capture that feeling of romantic misalignment so succinctly and poetically, while still spiking it with a dash of trademarked bitterness. (And so it’s no wonder the song appealed to the likes of Johnny Cash and Joan Baez!) But there’s something about Dylan’s original version, recorded as part of the one-night wine-fueled session that produced Another Side of Bob Dylan, that’s always been the most gripping. There’s slightest hint of drunken disdain in his voice as he enters the last verse, the heartbrokenness of his harmonica on each interlude: both serve to wring out the emotion of the song in a way no other performance of it quite manages. —Carter Shelter

14. “Shelter From The Storm”

Found on the wrenching masterpiece Blood On The Tracks, an album that explored the dissolution of Dylan’s marriage to his first wife, Sara, and on which the singer/songwriter shaded each song with subtle shifts to his voice and delivery, there’s a matter-of-factness to his performance. Accompanied only by his acoustic guitar and a quietly powerful bass part from Tony Brown, Dylan calmly unfurls the story of a man wrecked, hurt and damaged by the trials of his life who finds a welcoming presence in the repeated line “‘Come in,’ she said, ‘I’ll give you shelter from the storm.’” Through that plainspoken approach, it’s clear that he no longer believes that idea to be true, and in that calm, the raw pain is revealed. —Robert Ham

13. “It’s All Over Now, Baby Blue”

While many of the other tracks on the 1965 album Bringing It All Back Home had been part of his live repertoire for months before he hit Columbia Recording Studio to record the LP, and had therefore gone through various permutations along the way, this song was still fresh for Dylan. So his recording of “Baby Blue” was an attempt to maintain the raw inspiration of when he wrote it. Sometimes when lightning strikes, it leaves a permanent mark. In the years since, Dylan hasn’t pushed this symbolist masterpiece too far from its original rendition, letting the changes in his voice set the tone, which has, over the years, turned the song from an insistent farewell to the humble croon of the recording found on The Rolling Thunder Revue bootleg. —Robert Ham

12. “Mr. Tambourine Man”

There are few Dylan melodies as simple and stunning as 1965’s “Mr. Tambourine Man.” Bolstered by a minimal folk strum, the troubadour’s nasal pipes take center stage and portray the sort of youthful wonderment that would lead one to drop everything for “a trip upon a magic swirling ship.” Plenty more musicians have followed, too, with everyone from The Byrds to Judy Collins putting their own spin on the Bringing it All Back Home cut. A jingle-jangle morning —whatever that truly means, Dylan has never said —would be worth it every time. —Rachel Brodsky

11. “A Hard Rain’s A-Gonna Fall”

The Freewheelin’ Bob Dylan is really the first proper Bob Dylan record, and its tracklist is staggering, containing a number of not just classic Dylan songs, but classic songs period. “A Hard Rain’s A-Gonna Fall” is the stronger of the album’s two epics, and closes out the first side of the album with one of the finest protest songs he ever put to record. The political tumult of our current era makes some of the lyrics sound prophetic, or just reflects how little the situation ever really changes, only our awareness of it. As the apocalyptic fears that spawned the cultural tumult of the ‘60s once again rear their head, Dylan’s illumination of the failures of the human race hits like a punch in the gut. It’s lengthy verses read like a poem (and famed Beat poet/writer Allens Ginsberg has said that it was the first song he heard by Dylan and that it made him cry), but Dylan’s hypnotic guitar strumming and that repeated melody give a greater weight to his words. —Carter Shelter

10. “Masters of War”

“Masters of War” shows Dylan at his angriest. Although protest songs from his early work show peaceful dissidence (see: our No. 1) or visions of an apocalyptic future (“A Hard Rain’s A-Gonna Fall”), this track from 1963’s The Freewheelin’ Bob Dylan denounces the arms war of the 1960s. “Master’s of War” remains relevant in the Bush era and through the Iraq invasion. But what’s scarier than it’s continued resonance is the imagery of a grizzled, pencil-thin-mustachioed Dylan cursing, “And I hope that you die / And your death’ll come soon / I will follow your casket / In the pale afternoon / And I’ll watch while you’re lowered / Down to your deathbed / And I’ll stand o’er your grave / ’Til I’m sure that you’re dead.” —Hilary Saunders

9. “Subterranean Homesick Blues”

The song so captivating it left John Lennon in awe. Dylan going rock ‘n’ roll and aided by a band for the first time, slinging out anti-establishment beat poetry, and arguably foreshadowing rap, all packed into a blistering two minutes and twenty seconds. Maybe more than any other song in his unbeatable ‘60s output, “Subterranean” sounds like who Bob Dylan was in that era; filled with a rollicking energy and a venomous wit. To have set Bringing It All Back Home down on your record player in 1965 and hear this song come snapping it’s way out the speakers, would have been to hear budding revolution, both in Dylan and the world, something he would accomplish once again a few months later with “Like a Rolling Stone” and Highway 61 Revisited. —Carter Shelter

8. “Desolation Row”

“Desolation Row” is a difficult song to summarize. It was Dylan’s first song to crack the 10-minute mark (there are six in total) and it’s comprised of ten verses that each portray a new scene stuffed with literary characters, Biblical figures and real life people living surreal and tragic lives on the titular street. It is so sprawling, dense, referential, and metaphorical that it’s easy to read it as “nonsense masquerading as depth”:, but, for all the same reasons, “Desolation Row” is also the perfect song for Dylanphiles and English majors to endlessly dissect, analyze and interpret. Why are Romeo and Casanova punished for going there? What happened to Ophelia to make her an old maid at 22 years old? Why is Einstein disguised as Robin Hood and what is he doing sniffing drainpipes? Who is Dr. Filth and what are he and his nurse up to? Where even is Desolation Row? Whatever it may or may not mean, “Desolation Row” remains one of Dylan’s most potent and evocative songs, telling rich stories of a place rife with heartbreak, death, confusion, obfuscation, escape, sex and love. —Cameron Wade

7. “Don’t Think Twice, It’s All Right”

When making decisions, it’s oftentimes best not to second-guess yourself. It can lead to destructive thinking and obsessively creating “what if” scenarios in your head. That’s why “Don’t Think Twice, It’s Alright” is one of Bob Dylan’s greatest songs. It’s a classic Dylan tale that stresses the importance of moving on, despite the time and energy that has been devoted. While it’s an eloquent break-up song, it’s more importantly a song of empowerment, one that is a reminder that you sometimes have to be bold. The lyrics capture the back-and-forth between the certainty and doubt that follows such a decision as well as the inevitable bitterness of a relationship’s end: “You could have done better but I don’t mind / You just kinda wasted my precious time / But don’t think twice, it’s alright.” —Jaimie Cranford

6. “All Along The Watchtower”

Okay, we’ll say it: Hendrix’s version exceeds Dylan’s original. But while Bob Dylan couldn’t play like Hendrix or sing like Joan Baez, he could write songs better than any other human being. Here, he presents a bleak fantasy of epic proportions, all wrapped up in a just a few mere verses. When Dylan sings them, we see truth; when anybody else works them, we see all the truth contains. —Jason Rhode

5. “Visions of Johanna”

My San Francisco-born parents were about 19 when Dylan performed “Visions of Johanna” live for the first time, in nearby Berkeley. They weren’t there and you couldn’t have paid them to be. In fact, they were so put off by the voice David Bowie famously described as “sand and glue” that I doubt they even noticed Dylan was the author of all those songs they loved when Judy Collins or Joan Baez or Sandy Denny sang them. As a vocalist, I was also irritated by the adenoidal buzz of Dylan’s voice; so much so that most of his work only opened up for me when a good cover version lit it up. Often, it was Fairport Convention; occasionally it was Johnny Cash. But the masterpiece called out by U.K. Poet Laureate Sir Andrew Motion as the greatest song lyric of all time only really reached me through a bootlegged 1988 recording: The unlikely delivery mechanism was Robyn Hitchcock. But that was the voice that made me hear the poetic intensity of the lyric, the haunting, pensive structure of it, where the lack of a real chorus seems to bemoan and also celebrate the way nothing ever really comes to a satisfying close. The song draws on Beat poetry and T.S. Eliot and surrealism, and it is a godparent of the lyrics of, among others, Bruce Springsteen, Lou Reed and Joni Mitchell. It manages to be spare and lonely and at the same time lavish and densely packed. It is, at once, a quintessential Dylan song and a Dylan song for people who think they don’t like Dylan. It’s an exquisite trip down the border-road between poem and song. It’s also apparently the reason Robyn Hitchcock ever became a songwriter, which made sense the minute I heard him sing “The ghost of ‘lectricity howls in the bones of her face / where these visions of Johanna have now taken my place.” —Amy Glynn

4. “Tangled Up in Blue”

Dylan often introduces this song saying, “This took me 10 years to live and two years to write.” With “Tangled Up In Blue,” Dylan offers a Dante-esque account of an ongoing infatuation with a woman, similar to that of the Italian poet with his muse, Beatrice. Like the poet, Dylan crafts a concise and poetic narrative that showcases his talent for songwriting and storytelling. He even alludes to the famed lovers in the fifth verse, “Then she opened up a book of poems / And handed it to me / Written by an Italian poet / From the thirteenth century.” Though his allusion to the Divine Comedy is a running motif throughout the song, Dylan demonstrates literary talent of his own with his play on the color blue. Blue is often associated with sadness and depression but can also represent truth and wisdom. Paired with the tale of a profound love, the phrase “tangled up in blue” encapsulates both the pain and wisdom gained following a relationship’s end. As demonstrated here, Dylan’s ability to weave poetic elements into a cohesive song is why his work has extended beyond the music realm. —Jaimie Cranford

3. “The Times They Are A-Changin’”

Among Dylan’s protest songs, this one stands out for being unusually dewy-eyed. We often think of young Dylan as a boy with an old soul, but these lyrics aren’t wizened. They’re undeniably naïve, and that sort of sentiment within his body of work is refreshing. He pulls it off, capturing the optimism of both his budding generation and all youth movements since. Although the song came out in 1964, it doesn’t overtly mention the Civil Rights Movement; the nonspecific lyrics have allowed myriad listeners to project their causes onto his words. The times have always been a-changin’, but this song’s appeal never does. —Monica Hunter-Hart

2. “Blowin’ in the Wind”

The questions start small, almost like a toddler asking a parent why the sky is blue: “How many roads must a man walk down before you can call him a man?” Then the questions get grander: “How many years can a mountain exist before it’s washed to the sea?” And toward the end, the greatest, most unanswerable one: “How many deaths will it take till he knows that too many people have died?” Dylan’s Grammy-inducted protest anthem does not try to answer, because like so many of life’s greatest quandaries, the solutions are too complex to be neatly wrapped in a song verse. So Dylan settles on a few words: “Blowin’ in the wind.” With luck, the listener(s) will respond with an equal amount of wisdom and perspective. —Rachel Brodsky

1. “Like A Rolling Stone”

In an interview with critic Robert Hilburn, Dylan likened the inspiration that struck when he wrote “Like A Rolling Stone” to being possessed by a spirit. “It’s like a ghost is writing a song like that,” he said. “It gives you the song and goes away. You don’t know what it means. Except that the ghost picked me to write the song.” That specter hasn’t left Dylan in the 50 years since he spilled out pages and pages of what he called “vomit” and honed it down to four spiraling, spitting verses that culminate in that insistent chorus (“How does it feeeeeeeeeel?”). Just listen to one of the many live recordings of “Rolling Stone” available these days. You can taste the bile rising up in his throat as he sings, driving whatever backing band is blowing the wind into his sails.

The song haunted listeners from the jump, as well. Springsteen, Lennon, McCartney and Zappa all testified to its greatness after hearing that rifle crack of a snare hit that opens the song and Al Kooper’s meandering organ runs for the first time. Released as a single in 1965, it went to No. 2 on the Billboard Pop Charts, narrowly missing the top spot thanks The Beatles. Dozens of other artists—from Jimi Hendrix to Patti Smith—have recorded their own takes on it, finding fresh nuances within the hard assonance and embittered imagery of the lyrics. And for decades to come, you can be assured that there will be many more songwriters, poets, thinkers and dreamers that will get lost in those same rambling lines and become newly obsessed. Page after page has been written about “Like A Rolling Stone,” and it still feels like there’s more yet to say. —Robert Ham