Today, Bob Dylan, the best songwriter in the history of music, turns 75. It’s impossible to sum up a career that has spanned over fifty years, let alone condense it into a soporific “best of” list. Yet here we are. Here are Bob Dylan’s 75 best songs, in something resembling an order. I ignored bootleg albums, live albums (so no Before the Flood), collaborative albums (so no Basement Tapes) and cover albums (so no Good As I Been to You, World Gone Wrong, Shadows In the Night, or Fallen Angels).

(Author’s note: this was a stupid idea. Art is subjective, especially music, especially Dylan’s music. Some of your favorites won’t be here. Hell, some of my favorites won’t be here. I probably got a lot of this wrong. But I hope the six of you reading this enjoy it. Also, I know I forgot “With God on Our Side.” I love that song. It’s amazing. It should be here. But by the time I remembered it, I was done, and fuck you if you think I’m combing through this list again.)

UPDATE: I also forgot “Ballad of a Thin Man,” “It’s Alright, Ma (I’m Only Bleeding),” and “It Ain’t Me, Babe.” I might update this list in the next day or two to include them. My point is, this was not easy to do.

UPDATE 2: Okay, I went back in and added those four songs above, and in doing so excised “Silvio,” “Sweetheart Like You,” “It’s All Good,” and “The Man in Me.” You don’t care.

 

75. “All the Tired Horses” (Self Portrait, 1970)

The opening track from Dylan’s most reviled album is a curious song. Dylan doesn’t appear on it in any form. It consists of a single refrain (“All the tired horses in the sun/how am I supposed to get any riding done?”) yet gets more beautiful with each repetition. I want this song played at my wedding. And my funeral.

74. “I Feel a Change Comin’ On” (Together Through Life, 2009)

One of Dylan’s less impressive albums of the last fifteen years, Together Through Life reimagined Dylan as the drunk guy at the end of the bar. But here, he drops the facade and lets a sense of almost tangible wistfulness permeate his words.

73. “Bye and Bye” (“Love and Theft,” 2001)

Dylan indulges shamelessly in the tongue-in-cheek delivery that is the calling card of his 2001 masterpiece “Love and Theft.” Only he could sell lyrics like “I’m sitting on my watch, so I can be on time.”

72. “Long and Wasted Years” (Tempest, 2012)

This is one of the saddest-sounding songs on Tempest, and Tempest is an album that includes a song about John Lennon and one about the Titanic. Here Dylan’s drifter persona meets his tragic end, as he laments, “I haven’t seen my family in twenty years/that ain’t easy to understand/they may be dead by now/I lost track of them when they lost their land.”

71. “Spirit on the Water” (Modern Times, 2006)

This is not the first time that Dylan’s excellent 2006 album will show up on this list. In “Spirit on the Water,” with its playful guitar line, Dylan straddled the line between gleeful anachronism and underhanded menace.

70. “Clean Cut Kid” (Empire Burlesque, 1985)

Despite his insistence in his autobiography Chronicles Volume One that he isn’t “in” this song, there’s no mistaking Dylan’s anger as he rails against the military-industrial complex, with verses like “They said congratulations, you got what it takes/they sent him back into the rat race without any brakes.”

69. “Going, Going, Gone” (Planet Waves, 1974)

On his underrated studio reunion with The Band, Dylan managed to deliver a frank and unsettling look at a suicidal mindset. When he sings “I’m going, I’m going, I’m gone,” part of you wonders if you’ll see him again.

68. “Tin Angel” (Tempest)

Dylan’s nearly nine-minute tale of a scorned lover’s revenge blurs the lines between pulp and religious symbolism. It remains one of his darkest narratives.

67. “Floater (Too Much to Ask)” (“Love and Theft”)

The shaggy dog that is “Love and Theft” is summed up nicely here, with Dylan singing wryly about his grandparents, the boss’s son, and a new grove of trees. It’s as solid a slice of Americana as you’ll ever hear.

66. “Tight Connection to My Heart (Has Anybody Seen My Love?)” (Empire Burlesque)

Ignore the ’80s production: “Tight Connection” boasts some of Dylan’s most mysterious yet intimate lyrics of the decade. A lifetime of danger is implied in couplets like “I’m going to get my coat, I feel the breath of a storm/there’s something I gotta do tonight, you go inside and stay warm.”

65. “Quinn the Eskimo (The Mighty Quinn)” (Self Portrait)

The only hit to be borne of Self Portrait, “Quinn the Eskimo” is little more than a lark, yet it shows that even when he’s not trying that hard, Dylan can write a hell of a song.

64. “Beyond Here Lies Nothin'” (Together Through Life)

The first track of Together Through Life establishes the air of menace and dangerous romance that pervades the entire album.

63. “Born in Time” (Under the Red Sky, 1990)

Smack-dab in the middle of the otherwise execrable Under the Red Sky lies one of Dylan’s prettiest love songs.

62. “Dark Eyes” (Empire Burlesque)

Dylan’s overwrought 1985 album draws to an unexpectedly lovely, mysterious confusion. His lyrics here are some of his most alluring, and the stripped-down production adds an air of intimacy to the track.

61. “To Ramona” (Another Side of Bob Dylan, 1964)

Despite recording Another Side in a single day, Dylan managed to include, and perfect, one of is loveliest ballads. “To Ramona” stands out on the record among bitter kiss-offs like “Ballad in Plain D” and surreal dreamscapes like “Motorpsycho Nitemare.” It showed that the poet had a soul.

60. “You Ain’t Goin’ Nowhere” (Single, 1967)

Yes, this appeared eventually on The Basement Tapes, but for my money the best version of this song is the bare version featuring just Dylan, a guitar, and a banjo. You can hear the smile on his face when he sings about “a fish that walks and a dog that talks.”

59. “Where Teardrops Fall” (Oh Mercy, 1989)

For the second track of his best album of the ’80s, Dylan threw away the cynicism of “Political World” and “Everything is Broken,” delivering a Motown-tinged earworm of a song. The highlight: a saxophone solo by John Hart, reportedly done in one take.

58. “Forever Young” (Planet Waves)

One of Dylan’s most nakedly emotional songs, “Forever Young” at times borders on saccharine. But it’s impossible not to tear up when hearing Dylan’s unmasked love of his children.

57. “Po’ Boy” (“Love and Theft”)

“Man said Freddy/I said Freddy who/he said Freddy or not, here I come.” Only Bob Dylan could put a fucking knock-knock joke into a song and play it straight. And therein lies the humor of this “Love and Theft” standout.

56. “I Threw It All Away” (Nashville Skyline, 1969)

Dylan delivers a remorseful lament on his country-flavored album that closed out the ’60s. For such a mysterious figure, he wears his heart on his sleeve.

55. “Workingman’s Blues #2” (Modern Times)

Dylan infuses tinkling piano with a genuine sense of loss, bemoaning the state of the working man. Forty years into his career (and several million dollars richer than when he started out in Greenwich Village) he still believably cared about everyday Americans.

54. “The Lonesome Death of Hattie Carroll” (The Times They Are A-Changin’, 1964)

Dylan fudged the facts of the murder case of Hattie Carroll and her killer, the heir William Zantzinger. But he got to the emotional truth of the matter.

53. “Positively Fourth Street” (Single, 1964)

In a song named for the New York street where Dylan once resided, he took aim at the fairweather fans and acolytes who abandoned him as soon as it became fashionable to do so. He wishes they could stand in his shoes, not so they could understand him, but so they “could see what a drag it is to see you.” He’s rarely sounded angrier.

52. “If Not for You” (New Morning)

One of Dylan’s most low-key ballads, “If Not for You” makes love sound casual and fun. But it’s not without its sense of maturity; there’s a reason that this was one of George Harrison’s favorite Dylan songs.

51. “Love Sick” (Time Out of Mind, 1997)

Dylan’s mid-90s masterpiece starts off stark and terrifying. His voice, long since having collapsed, croaks out the opening line “I’m walking through streets that are dead,” and it heralds the arrival of a new Bob Dylan.

50. “Ring Them Bells” (Oh Mercy)

Dylan, his piano, and his god. His evangelical Christian phase was long over by the time Oh Mercy came around, but on “Ring Them Bells” he did a remarkable job of conveying the depth of his faith.

49. “Brownsville Girl” (Knocked Out Loaded, 1986)

Dylan co-wrote this eleven-minute opus with the Pulitzer Prize-winning playwright and actor Sam Shepard, and seldom have his theatrical and cinematic ambitions been so obvious. “Brownsville Girl” has an infectious chorus and a cast of misfits, liars, thieves, and murderers – in short, it’s a classic Dylan song.

48. “Can’t Wait” (Time Out of Mind)

“That’s how it is when things disintegrate.” In many ways, “Can’t Wait” is a perfect summation of Time Out of Mind‘s themes of heartbreak, fragility, and mortality.

47. “High Water (For Charley Patton)” (“Love and Theft”)

Propelled by ominous kettle drums and a propulsive banjo melody, “High Water” is the scariest song on one of Dylan’s best albums. It sounds like a warning, but one that has come far too late.

46. “Hurricane” (Desire, 1976)

Factually inaccurate though it may be, “Hurricane” was Dylan’s first openly political song since the 1960s. His anger and vitriol are palpable here, and when he spits out the N-word it sounds more like a bullet than an epithet.

45. “Things Have Changed” (Wonder Boys soundtrack, 2000)

Dylan won an Oscar for his nihilistic, resigned inversion of “The Times They Are A-Changin’.” Over one of his most recognizable melodies, Dylan rasped “I used to care, but things have changed.” The so-called troubadour of conscience had officially washed his hands of the counter culture.

44. “Song to Woody” (Bob Dylan, 1962)

One of only two original songs on Dylan’s debut album, “Song to Woody” showcased his lyrical prowess early in his career. First performed for Woody Guthrie in a hospital in New Jersey, the song’s title and opening lines would inspire David Bowie’s “Song to Bob Dylan,” itself a classic in its own right. With lines like “Here’s to the hearts and the hands of the men/who come with the dust and are gone with the wind” Dylan asserted his identity as someone ages older than he appeared.

43. “Isis” (Desire)

One of Dylan’s best adventure songs – with the possible exception of “Bob Dylan’s 115th Dream” – “Isis” employs a hapless hero in a Western setting, going against impossible, surreal odds. Sound like anyone we might know? It’s just too bad that now it’s unfashionable to go around saying “I love ‘Isis.'”

42. “Blowin’ in the Wind” (The Freewheelin’ Bob Dylan, 1963)

Dylan’s prototypical protest song is one he would later dismiss, saying he wrote it in a matter of ten minutes. Not bad for an anthem adopted by seemingly an entire generation. He’d have better lyrics and better melodies in the years to come, but few of his songs would have anything close to the impact of “Blowin’ in the Wind.”

41. “Roll On John” (Tempest)

It only took thirty-one years for Dylan to write a eulogy to his friend John Lennon. In the seven minutes of “Roll On John” Dylan manages to sound wistful, regretful, and even a bit cynical – not unlike Lennon itself. Plus, he manages to incorporate Beatles lyrics into the song without sounding sacreligious.

40. “With God on Our Side” (The Times They Are A-Changin’)

This is a masterful, bitter polemic boasting some of Dylan’s deceptively saddest lyrics. “You don’t count the dead when God’s on your side,” he laments. The only reason it’s not higher on this list is because of an ugly, dated verse about Russia, one thankfully omitted for the brilliant performance on MTV Unplugged. 

39. “Not Dark Yet” (Time Out of Mind)

On Time Out of Mind‘s bleakest song, Dylan repeats “It’s not dark yet, but it’s getting there.” At the time of the album’s release, Dylan was recuperating from near-fatal heart problems, and in “Not Dark Yet” it sounds like he’s eulogizing himself.

38. “The Man In the Long Black Coat” (Oh Mercy)

Dylan’s most ominous melody is the perfect backdrop to his dark parable of the titular demonic figure. Dylan’s Christian phase might have been years in the past, but on “The Man In the Long Black Coat” he showed that Biblical darkness was never far from the surface.

37. “Make You Feel My Love” (Time Out of Mind)

Once derided for “Hallmark card lyrics,” this song has since become one of Dylan’s most beloved ballads. For once, he dropped his cool, aloof persona, and allowed listeners to get a glimpse of the man underneath all the layers. Dylan’s creaky-floorboard rasp gave the song life, but it was improved even more by Adele’s Shirley Bassey-style take on the song, on her debut album 19.

36. “Summer Days” (“Love and Theft”)

The song once described as sounding like “the moment that blues became rock and roll,” “Summer Days” is the most high-energy number on “Love and Theft,” and the best showcase for Dylan’s band on the whole album.

35. “Shelter From the Storm” (Blood on the Tracks, 1975)

Dylan’s most hopeful refrain – “‘Come in,’ she said, ‘I’ll give you shelter from the storm'” – is a welcome life raft in the sea of despair that Blood on the Tracks was born in. The song also boasts some of Dylan’s most indelible imagery. Who can ever forget “In a little hilltop village, they gambled for my clothes”? In anyone else’s hands, that would be a chapter in a novel. In Dylan’s hands, it’s an almost-throwaway line in a single song.

34. “All Along the Watchtower” (John Wesley Harding, 1967)

Some of Dylan’s most inscrutable lyrics engendered the best cover version of any of his songs, performed by Jimi Hendrix on Electric Ladyland. “Watchtower” breaks up the cowboy-folklore themes of John Wesley Harding, and gave a glimpse of a weirder, darker America lurking beneath the surface.

33. “Tonight I’ll Be Staying Here With You” (Nashville Skyline)

This song doesn’t have the depth of feeling that other songs on this list do, but Dylan’s joyful vocals make it seem as though we’re sharing in his revelation. As soon as he decides to throw away his bags and ticket, we’re in for the ride. A simple but marvelously written song.

32. “Every Grain of Sand” (Shot of Love, 1981)

One of Dylan’s final religious songs reaches the same heights as his classic folk compositions. “Every Grain of Sand” doesn’t feel like it was written by an actual person; rather, it sounds like a ballad that Dylan heard from one of his Greenwich contemporaries. It’s the most honest expression of Dylan’s faith – it makes it real, understandable, and tangible.

31. “Stuck Inside of Mobile With the Memphis Blues Again” (Blonde on Blonde, 1966)

Here Dylan uses his propensity for surreal imagery to rollicking, dizzying, hilarious effect. At seven minutes long, the song breezes by, and it sounds like a travel brochure for Dylan’s own weird corner of the country.

30. “Trying to Get to Heaven” (Time Out of Mind)

One of the more nakedly autobiographical songs on Time Out of Mind, “Trying to Get to Heaven” imagines a Dylan not all too different from the one singing the song. There’s always been a disconnect between the singer and the song, but here the distance is compressed. “I’ve been to Sugar Town, I shook the sugar down,” Dylan sings, and while the meaning isn’t clear, the experience behind the words is unmistakable.

29. “Nettie Moore” (Modern Times)

There’s a real sense of loss to the simple refrain of this song: “Oh, I miss ya, Nettie Moore.” With one of the sparsest melodies on Modern Times, Dylan spins a tale of love and longing, all while remaining in the abstract. It’s a near-perfect balance between his many selves.

28. “The Times They Are A-Changin'” (The Times They Are A-Changin’)

In 1964, when this album came out, JFK had just been assassinated and the Vietnam War was in full swing. In 2008, America elected its first black president. “The Times They Are A-Changin’,” itself a timeless song, has been relevant, and – dare I say? – timely since the day it was written.

27. “Pay in Blood” (Tempest)

This might be the best song off of one of Dylan’s darkest albums. “I pay in blood,” he croaks, “but not my own.” It sounds like he has a guitar in one hand and a straight razor in the other. This is Dylan’s greatest post-“Mississippi” song.

26. “Changing of the Guards” (Street-Legal, 1977)

Street-Legal is a kaleidoscopic portrait of an America that probably never existed outside of Dylan’s imagination, and the album’s opening track is the best example of that. Featuring what might be his strangest couplet (“They shaved her head/she was torn between Jupiter and Apollo”), “Changing of the Guards” also employs some of Dylan’s most vivid images of a surreal apocalypse.

25. “Sad-Eyed Lady of the Lowlands” (Blonde on Blonde)

Written, according to the song “Sara,” for his then-wife Sara Lowndes, “Sad-Eyed Lady” perfectly captures the hazy, dreamlike state in which Dylan wrote the song. It’s also a welcome relief from the loose, jangly production that characterizes Blonde on Blonde.

24. “Idiot Wind” (Blood on the Tracks)

One of Dylan’s most ferocious, biting songs, “Idiot Wind” wears its derision on its sleeve, as Dylan wrings every ounce of loathing out of the refrain “You’re an iiiidiot, babe.” Is it political? Personal? Any reason it can’t be both?

23. “I Want You” (Blonde on Blonde)

Dylan loved this song so much that I Want You was almost the title of the album it appears on. His joy is palpable. Into an atypically plainspoken chorus (“I want you/so bad”) he packs glee, romance, and even a bit of lust.

22. “You’re Gonna Make Me Lonesome When You Go” (Blood on the Tracks)

My friend and fellow critic Nate put it best: For any other artist, this would be the best song of their career; for Dylan, it’s not even the best on the album.

21. “It’s All Over Now, Baby Blue” (Bringing It All Back Home, 1965)

Dylan’s gentlest goodbye. “Strike another match, go start anew,” he intones, and in the chorus the nickname “baby blue” isn’t infantilizing, it’s endearing. Whoever he’s singing to, he cares for a great deal. There’s a heartbreaking intimacy on display here; it acts as a precursor of sorts to Blood on the Tracks. 

20. “Don’t Think Twice, It’s Alright” (The Freewheelin’ Bob Dylan)

This is like a photo negative of “Baby Blue.” Over a melody no less gentle, Dylan lays some of his most biting lyrics. When he sings “You just kinda wasted my precious time,” one wonders if it’s only because he couldn’t say “fuck you” on the radio.

19. “Maggie’s Farm” (Bringing It All Back Home)

A song so angry, vicious, and funny that it could only have been done justice by Rage Against the Machine, who covered it in 2000. Dylan’s anger on behalf of mistreated farm workers would eventually lead to the organization of Farm Aid in the 1980s.

18. “It Ain’t Me, Babe” (Another Side of Bob Dylan)

One of Dylan’s most famous compositions, covered by everyone from Johnny Cash to Elvis Presley, “It Ain’t Me, Babe” is still the gold standard for songs about romantic incompatibility, as well as the greatest “it’s not you, it’s me” ever recorded.

17. “Just Like Tom Thumb’s Blues” (Highway 61 Revisited, 1965)

“When you’re lost in the rain in Juarez and it’s Easter time too.” Thus begins Dylan’s foray into beat poetry. The influence of writers like William S. Burroughs and Allen Ginsberg (himself an eventual acolyte of Dylan’s) is on plain display, yet “Tom Thumb’s Blues” never feels like it owes a debt to anyone.

16. “Shooting Star” (Oh Mercy)

A lovely coda to Dylan’s Christian phase, “Shooting Star” was the last song on his last album of the ’80s. In it, he laments his failure as a Christian, all in the guise of a love song: “It’s too late to say the things to you/that you needed to hear me say.” Its subject is almost universal, and in a roundabout way, that makes it one of Dylan’s most successful religious songs.

15. “Subterranean Homesick Blues” (Bringing It All Back Home)

Few people know this, but rap was invented in 1965 by a 24-year-old Jewish kid from Minnesota. “Subterranean” remains one of the most dizzying displays of Dylan’s lyrical dexterity, with a deceptively difficult rhyme scheme.

14. “Tombstone Blues” (Highway 61 Revisited)

A classic Dylan collage of characters historical, fictional, and mythical. He doesn’t employ traditional refrains all that often (and he especially didn’t in the ’60s), but “Tombstone Blues” boasts one of his catchiest.

13. “Ballad of a Thin Man” (Highway 61 Revisited)

Dylan’s “fuck off” to the journalism world at large unspools over a minor-key piano line that wouldn’t sound out of place in a saloon in a mental institution. “Something is happening here, but you don’t know what it is/do you, Mr. Jones?” is still one of his most damning accusations.

12. “Lay Lady Lay” (Nashville Skyline)

The saddest, prettiest song on Nashville Skyline remains the best showcase for his voice. People have always derided Dylan as a singer, but here it’s impossible not to be moved by lines like “Whatever colors you have in your mind/I’ll show them to you and you’ll see them shine.”

11.”It’s Alright, Ma (I’m Only Bleeding)” (Bringing It All Back Home)

The best track from the acoustic half of Bringing It All Back Home contains one of Dylan’s most pointed barbs at the establishment. The lyric “Even the President of the United States sometimes must have to stand naked” was received to rapturous applause every time it was performed, which you can hear on Before the Flood.

10. “Visions of Johanna” (Blonde on Blonde)

“These visions of Johanna keep me up past the dawn.” They’d have the same effect on all of us, Bob. At seven minutes, this isn’t even the longest track on Blonde on Blonde, but it helped solidify Dylan’s reputation as one of popular music’s best long-form storytellers.

9. “I Shall Be Released” (Single, 1968)

Another throwaway song that became an anthem, this time for the civil rights movement. Fifty years on, he’s written few lyrics with the hopefulness of “I see my light come shining.” The Band would release this first, on their debut album Music From Big Pink, and Richard Manuel’s falsetto brings the song to stark, beautiful life.

8. “Mr. Tambourine Man” (Bringing It All Back Home)

Some of Dylan’s most surreal lyrics managed to encapsulate the turbulent 1960s, when it felt like the whole country was stuck in a jingle-jangle morning. “There is no place I’m going to” is catchy, mysterious, and ultimately nihilistic. It’s a shame that the Byrds won more acclaim for their dull, insipid cover of the song.

7. “Desolation Row” (Highway 61 Revisited)

Dylan makes Desolation Row both alluring and forboding – people are always trying to escape from it or to it. Here you’ll find Casanova, T.S. Eliot, the Hunchback of Notre Dame, the Phantom of the Opera, and Cinderella. There are characters of all origins and nationalities here, so why does the song sound so American? A lot is owed to the flamenco-inspired guitar line, provided by session guitarist Charlie McCoy.

6. “Highway 61 Revisited” (Highway 61 Revisited)

Fifty-one years after the release of Highway 61, rock and roll has never had a better opening line than “God said to Abraham, kill me a son.” Here he combines Abraham, Isaac, and God with folk-song characters like Louis the King and Poor Howard. This is as close to a perfect Dylan song as you’ll ever hear.

5. “Knockin’ on Heaven’s Door” (Pat Garrett and Billy the Kid, 1973)

While writing the music for Sam Peckinpah’s Pat Garrett, Dylan managed to write one of his enduring classics, a two and a half minute meditation on death, with unforgettable images like “that long black cloud is coming down.” He’d never write a better song about death than this one. (He also, while screwing around with a song called “Rock Me Mama,” wrote the chorus to perennial country favorite “Wagon Wheel.” You can hear Dylan’s take of it on Peco’s Blues.)

4. “A Hard Rain’s A-Gonna Fall” (The Freewheelin’ Bob Dylan)

Dylan at his most prophetic sings of a land where “black is the color and none is the number.” “Hard Rain” contains Dylan’s most terrifying imagery, and the sense of futility is enough to bring tears to your eyes. This remains his scariest song – and one of his most plausible.

3. “Mississippi” (“Love and Theft”)

A shaggy dog story, “Mississippi” is the track on which Dylan perfect the grizzled, wise-cracking drifter persona he adopted for “Love and Theft.” It also contains some of his sweetest lyrics: “I need something strong to distract my mind/I’m gonna look at you ’til my eyes go blind.” Fifteen years after its release, “Mississippi” remains the best Dylan song of the twenty-first century, and an all-time classic.

2. “Tangled Up in Blue” (Blood on the Tracks)

Dylan famously said of “Tangled Up in Blue” that it took him ten years to live and two years to write. The best song from his best album transmogrifies that experience, that longing, and that heartbreak into some of Dylan’s best work as a lyricist. One wonders if it was too personal for Dylan; several times since Blood‘s release, he’s changed the pronoun “I” to “he.”

1. “Like a Rolling Stone” (Highway 61 Revisited)

What else is there to say about the greatest opening track ever written? Rolling Stone called it the best song of all time. Greil Marcus wrote an entire book about it. It was an atom bomb dropped on the folk scene, and it made the best case for Dylan as someone who played by no one’s rules but his own. Every song on this list is great. Most are classics. “Like a Rolling Stone,” though, is timeless.

 

Happy birthday, Bob.

 

 

About Author