The 80 Greatest Bob Dylan Songs (in Honor of His 80th Birthday)

Below is a list of my 80 favorite Bob Dylan songs in honor of his 80th birthday later this month. I started compiling this list a year ago and have been continually revising it – as well as the thumbnail reviews accompanying it – ever since. During this process, many songs were on the list at one point, only to fall off and be replaced by other songs that I realized, in my heart of hearts, I loved more. This is not an attempt to be objective or acknowledge Dylan’s most important songs (there are plenty of other lists like that already). This is simply a list of what I consider to be the greatest Dylan songs based on my own personal point-of-view as a Dylan fan of 30+ years. I’ve also created a Spotify playlist that functions as a countdown of the top 80, which you can stream here. Enjoy!

80. Death is Not the End (Down in the Groove, 1988)
Probably best known for Nick Cave’s cover version, this is a gospel song with a sweet melody, a killer sense of humor and backing vocals by Brooklyn hip-hop collective Full Force.

79. Song to Woody (Bob Dylan, 1962)
Dylan’s tribute to his most important formative influence also announced his arrival as a songwriter.

78. What Can I Do For You? (Saved, 1980)
The harmonica solo on this, one of Dylan’s greatest, has a pleading quality that captures the song’s devotional message as well as the lyrics do.

77. Just Like Tom Thumb’s Blues (Highway 61 Revisited, 1965)
I’ve always loved the counterpoint between the warmth of Paul Griffin’s barroom-piano playing and the feeling of dislocation imparted by the lyrics.

76. Long and Wasted Years (Tempest, 2012)
A Rolling Stone critic astutely compared this to Martin Scorsese’s The Irishman in that it features a narrator who no longer has anything, looking back on a lifetime of regret.

75. Sign on the Window (New Morning, 1970)
Probably the most obscure song on this list, this is Dylan’s most sublime ode to domestic tranquility.

74. Dignity (recorded during the Oh Mercy sessions in 1989, released on Greatest Hits Vol. 3, 1994)
Who but Dylan would write a song taking “dignity” as its subject, not to mention personifying that quality as a character in a detective story?

73. Lay, Lady, Lady (Nashville Skyline, 1969)
Dylan’s sexiest song ever, sung in his “country crooner” voice.

72. Dark Eyes (Empire Burlesque, 1985)
A solo acoustic ballad with highly poetic lyrics, purportedly inspired by Dylan looking into the eyes of a prostitute in a hotel lobby, this stands out like a diamond in a coal mine on the otherwise overproduced Empire Burlesque.

71. Lenny Bruce (Shot of Love, 1981)
A surprising, deeply moving piano-driven tribute to the late comedian.

70. Forgetful Heart (Together Through Life, 2009)
Like a dark sequel to 1981’s “Heart of Mine,” Dylan addresses his heart as if it had a mind of its own.

69. Blowin’ in the Wind (The Freewheelin’ Bob Dylan, 1963)
Dylan’s most covered song ever, and arguably his most important, this was the “big bang” of the notion that folk music would serve as the soundtrack to the Civil Rights movement.

68. I and I (Infidels, 1983)  
This ominous sounding, reggae-tinged blues song nods to Rastafarianism as well as Dylan’s lifelong obsession with Rimbaud’s phrase “Je est un autre.”

67. The Man in Me (New Morning, 1970)
Best known as the main-title theme of The Big Lebowski, this is one of the catchiest creations in the whole Dylan songbook.

66. I Shall Be Released (recorded in 1967 during the Basement Tapes sessions, released on Biograph, 1985)
This gospel-influenced song about a prisoner (perhaps literal, perhaps figurative) yearning for redemption is one of the highlights of the Basement Tapes sessions.

65. Forever Young (Planet Waves, 1974)
Dylan wrote this prayer-like song for one of his children and it deservedly became an instant wedding/graduation/birthday-party staple.

64. Summer Days (“Love and Theft”, 2001)
Next to his 2009 cover of “Must Be Santa,” this is probably the fastest song Dylan ever recorded (as well as one of the most fun).

63. The Times They Are a-Changin’ (The Times They Are a-Changin’, 1964)
The ultimate protest anthem, cutting but never preachy, this sounds as relevant today as it did upon its release 57 years ago.

62. One More Cup of Coffee (Desire, 1976)
Allen Ginsberg aptly described Dylan’s singing here as “Hebraic cantillation.”

61. Simple Twist of Fate (Blood on the Tracks, 1975)
This sad story-song about a relationship fated not to work out is the broken heart of Blood on the Tracks.

60. Ring Them Bells (Oh Mercy, 1989)
An indelible, descending piano chord progression combines with lyrics that plead for compassion for the less fortunate of this world.

59. The Lonesome Death of Hattie Carroll (The Times They Are a-Changin’, 1964)
Dylan used a newspaper article about a real-life murder to form the basis of this haunting masterpiece about a tragic miscarriage of justice.

58. I’ve Made Up My Mind to Give Myself to You (Rough and Rowdy Ways, 2020) 
This beautiful recent song can be interpreted as addressing a lover, a higher power, or Dylan’s own fanbase.

57. Stuck Inside of Mobile with the Memphis Blues Again (Blonde on Blonde, 1966)
I always felt that the groovy organ playing and snappy drumming on this rollicking number were exactly what Dylan had in mind when he described Blonde on Blonde as featuring “that thin, wild mercury sound.”

56. Born in Time (Under the Red Sky, 1990)
Dylan’s most mystical love song.

55. When He Returns (Slow Train Coming, 1979)
Jean-Luc Godard has used this song in three different movies in three different decades.

54. Tears of Rage (recorded in 1967, released on The Basement Tapes, 1975)
One of Dylan’s most multitudinous lyrics — it manages to contain the Bible, King Lear and the Declaration of Independence — set to a gorgeous melody by The Band’s Richard Manuel.

53. Every Grain of Sand (Shot of Love, 1981)
The highlight of Dylan’s entire gospel period, the Blakean lyrics are best served by the minimalist acoustic-guitar-and-piano-arrangement of the demo version included on The Bootleg Series Vol. 3.

52. Things Have Changed (single, 2000)
The song that inaugurated Dylan’s great late period (which saw him bring his Never Ending Tour band into the studio for the first time and serve as his own producer), this Oscar-winning acoustic rocker is also quite danceable.

51. Sara (Desire, 1976)
One of Dylan’s most nakedly autobiographical songs, in which he looks back on a family vacation from the vantage point of estrangement from his first wife, I sometimes find this too painful to listen to.

50. Girl from the North Country (The Freewheelin’ Bob Dylan, 1963)
A simple, perfect love song.

49. I Dreamed I Saw St. Augustine (John Wesley Harding, 1967)
My favorite cut from John Wesley Harding, which I’ve always loved for the sparseness of the arrangement (just one acoustic guitar, bass and drums) and the dreamy, parable-like quality of the lyrics.

48. If You See Her, Say Hello (Blood on the Tracks, 1975)
Another devastating song: “She might think that I’ve forgotten her / Don’t tell her it isn’t so.”

47. It’s Alright Ma (I’m Only Bleeding) (Bringing It All Back Home, 1965)
Some lamented that Dylan had abandoned “protest music” after 1964’s The Times They Are A-Changin’ but a track like this, featuring an astonishing, seemingly never-ending torrent of words, proved that he had merely broadened his concerns in order to protest the insanity of living in the modern world.

46. Pay in Blood (Tempest, 2012)
This Rolling Stones-esque rocker is as musically infectious as it is lyrically vicious.

45. Where Are You Tonight? (Journey Through Dark Heat) (Street-Legal, 1978)
The most underrated song on Dylan’s most underrated album (which, more than Blood on the Tracks, is his real “divorce album”), this desperate-sounding track is pop music at the end of its tether.

44. Tomorrow is a Long Time (live recording from 1963, released on Greatest Hits Vol. 2, 1971)
Dylan justifiably cited Elvis Presley’s version of this as his favorite cover of any of his own songs.

43. Tryin’ to Get to Heaven (Time Out of Mind, 1997)
A moving song about rambling through the world, this features two fantastic “electric” harmonica breaks in which the sound of Dylan’s harp was driven through a distortion box.

42. Shelter from the Storm (Blood on the Tracks, 1975)
I’m obsessed with the hard-rocking live 1976 version of this song about seeking refuge in the arms of another person, featuring one of Dylan’s most impassioned vocals and his sick, but rarely displayed, slide-guitar playing.

41. Chimes of Freedom (Another Side of Bob Dylan, 1964)
A lyrical tour de force about looking at a thunderstorm and imagining that the lighting is somehow flashing in solidarity with everyone who has ever felt downtrodden or dispossessed.

40. High Water (For Charley Patton) (“Love and Theft”, 2001)
A tribute to one of the great Delta bluesman that is, perhaps perversely, not a blues itself but rather a banjo-driven folk song full of memorable apocalyptic imagery.

39. Senor (Tales of Yankee Power) (Street-Legal, 1978)
The most famous song on Street-Legal, and the one Dylan has played live the most often, this minor-key ballad is dark, brooding and awesome.

38. Boots of Spanish Leather (The Times They Are a-Changin’, 1964)
Not many songwriters have even attempted to write an epistolary song but this is one of the greatest examples of the genre.

37. Abandoned Love (recorded during the Desire sessions in 1975, released on Biograph in 1985)
Left off the album for which it was recorded and shelved for a decade, this violin-driven love song would’ve been the crowning achievement of anyone else’s career.

36. Positively 4th Street (single, 1965)
Dylan’s ultimate “fuck you” song, this catchy 1965 single convinced Joni Mitchell that lyrics could be literature and that she could become a professional singer/songwriter herself.

35. Most of the Time (Oh Mercy, 1989)
The rhetorical genius of this song is that, by relentlessly repeating how content he feels the majority of the time, the narrator makes the listener acutely aware of how heartbroken he secretly is by what he doesn’t say (i.e., describing how he feels the rest of the time).

34. Nettie Moore (Modern Times, 2006)
So memorable for the vocal melody, which sees Dylan’s voice rise and fall with every line in the verses, and a sparse musical arrangement highlighted by George Receli’s metronomic, heartbeat-like drumming.

33. Lay Down Your Weary Tune (recorded 1963, released on Biograph, 1985)
An incredible early song about communing with nature and hearing “music” in the sounds of the natural world.

32. Highlands (Time Out of Mind, 1997)
Dylan’s second longest song ever sees him talk-singing over a blues riff: he laments his vanished youth, gives shout-outs to Neil Young and Erica Jong and, for one uproariously funny verse, has a sexy and tense flirtation with a waitress in a Boston restaurant.

31. Caribbean Wind (recorded during the Shot of Love Sessions in 1981, released on Biograph, 1985)
Dylan spent a lot of time in the Caribbean in the early 1980s, which inspired some great wordy songs, and this galloping number, with delightful “wind” sounds provided by the female backup singers, is one of the best.

30. It Ain’t Me, Babe (Another Side of Bob Dylan, 1964)
An exquisite anti-love song and a farewell to the purists in the folk-revival movement all rolled up in one.

29. Black Diamond Bay (Desire, 1976)
One of the best of the long story-songs on Desire, unforgettable for its crazy “wrap-around rhymes” (“veranda…and a”) and a surprise ending that shifts from the third to the first person.

28. Mother of Muses (Rough and Rowdy Ways, 2020)
Perhaps inspired by the engraving on the back of his Nobel Prize for Literature medal, Dylan explicitly invokes his muse on this lyrically majestic, melodically intricate and tenderly sung song.

27. Don’t Think Twice, It’s All Right (The Freewheelin’ Bob Dylan, 1963)
The delicacy of Dylan’s finger-picking and his emotional singing reveal an affection for the object of this song that is missing from the spiteful lyric.

26. Knockin’ on Heaven’s Door (Pat Garrett & Billy the Kid, 1973)
Three simple chords and Dylan’s most unforgettable sing-along chorus have made this so famous that a lot of folks don’t even know that he wrote it.

25. Standing in the Doorway (Time Out of Mind, 1997)
The most potent song about heartache on an album chock-full of songs about heartache.

24. I Want You (Blonde on Blonde, 1966)
Everyone should hear this ecstatic love song and feel like it describes how they’ve felt about another human being at least once in their lives.

23. Man in the Long Black Coat (Oh Mercy, 1989)
Almost indescribably spooky and divine, like a Nathaniel Hawthorne short story set to music.

22. Workingman’s Blues #2 (Modern Times, 2006)
The way Dylan’s vocal melody confidently rolls and flows over the chords from Pachelbel’s Canon – as he poignantly pays tribute to the working class – rarely fails to bring a tear to my eye.

21. Red River Shore (recorded during the Time Out of Mind sessions in 1997, released on Tell-Tale Signs, 2008)
Jesus Christ, Bob: “Some of us turn off the lights and we laugh in the moonlight shooting by /
Some of us scare ourselves to death in the dark to be where the angels fly.”

20. Jokerman (Infidels, 1983)
I was a child when this came out and, although I didn’t first hear it until later, its provocative mixture of socio-political commentary and biblical imagery conjures up the early 1980s for me like no other song.

19. A Hard Rain’s A-Gonna Fall (The Freewheelin’ Bob Dylan, 1963)
If “Blowin’ in the Wind” proved popular songs could address social issues and “Don’t Think Twice” gave birth to the singer/songwriter “confessional” genre, “Hard Rain” showed it was possible to write epic songs influenced by serious literature (in this case, Romantic, French Symbolist and Beat poetry).

18. Hurricane (Desire, 1976)
Thank God Dylan had to re-cut this with altered lyrics in order to avoid being sued for libel — the version that ended up on Desire, with its faster tempo (and Ronee Blakley’s valiant attempts to sing along on the chorus), is the definitive version of this supremely cinematic song.

17. Mr. Tambourine Man (Bringing It All Back Home, 1965)
Incomparably lovely for Bruce Langhorne’s subtle electric guitar playing and some of Dylan’s finest ever lyrics (the “Take me disappearing through the smoke rings of my mind” verse, in particular, is solid gold).

16. Mississippi (“Love and Theft”, 2001)
If the musical genre known as “Americana” didn’t exist, it could be recreated entirely by using only this song as a seed.

15. Changing of the Guards (Street-Legal, 1978)
Mixing imagery drawn from Tarot cards and the life of Joan of Arc, this wild song features a wailing saxophone and call-and-response vocals with a female chorus that will get your adrenaline pumping like nothing else Dylan has done.

14. Series of Dreams (recorded during the Oh Mercy sessions in 1989, released on The Bootleg Series Vol. 1-3, 1991)
The best song anyone ever wrote about dreaming, the feeling of which is accurately conveyed through the surreal lyrics and the elaborate, wall-of-sound production.

13. Desolation Row (Highway 61 Revisited, 1965)
One of Dylan’s most ambitious works, the 11-minute-plus opus that closes Highway 61 Revisited weaves together a large cast of characters (from history, the Bible, literature, etc.) into a chugging, panoramic epic that single-handedly expanded the artistic possibilities of popular song.

12. Blind Willie McTell (recorded during the Infidels sessions in 1983, released on The Bootleg Series Vol. 1-3, 1991)
Dylan’s soulful piano playing, Mark Knopfler’s nimble fretwork, a melody inspired by “St. James Infirmary Blues” and lyrics that address the ghosts of slavery and the cathartic power of the blues are the ingredients of this timeless masterpiece.

11. Tangled Up in Blue (Blood on the Tracks, 1975)
The principles of Cubist painting applied to narrative songwriting — where the story of a man and woman splitting up (and perhaps reconnecting) in the wake of the death of the ’60s counterculture — is told alternately in the third and first person, and is somehow more effective because of it.

10. Murder Most Foul (Rough and Rowdy Ways, 2020)
Dylan’s longest song is also his largest song. It’s less about the assassination of JFK than it is about the healing power of art in a time of collective trauma (you know, like the COVID-19 pandemic). It’s his grandest poetic statement, the centerpiece of his most unified album, the Damascus to which all of the other songs on Rough and Rowdy Ways lead. To give oneself over to it for the entirety of its 17 minutes is to become hypnotized and feel time flowing forwards and backwards simultaneously. There’s nothing else like it in the history of recorded music — by Dylan or anyone else.

9. Like a Rolling Stone (Highway 61 Revisited, 1965)
The greatest rock and roll song of all time, or “La Bamba” for intellectuals.

8. Tempest (Tempest, 2012)
This isn’t a song about the sinking of the Titanic. It’s a song about someone dreaming about the sinking of the Titanic, an ingenious conceit that unmoors Dylan’s long narrative song from historical reality and allows him to fill it up with crazy, Hieronymous Bosch-like visions. There is incredible variety and expressiveness in his singing, and the delightful Celtic melody always makes me want to sway a mug of beer to and fro and try to sing along.

7. Not Dark Yet (Time Out of Mind, 1997)
The lofty peak of Time Out of Mind, released after Dylan had contracted a near-fatal fungal heart infection, which colored its reception forever after. As the great literary scholar Christopher Ricks points out, this poignant and beautiful song features a narrator, like John Keats in “Ode on a Grecian Urn,” who is “half in love with easeful Death.”

6. Sad-Eyed Lady of the Lowlands (Blonde on Blonde, 1966)
Tom Waits said this song made him think of “a drifter around a fire with a tin cup under a bridge remembering a woman’s hair.” And I think I know what he means.

5. Ain’t Talkin’ (Modern Times, 2006)
Dylan’s darkest ever song, in which a first-person narrator wanders a post-apocalyptic landscape that has seemingly been abandoned by God (“The gardener is gone”). The popular-song equivalent of an Ingmar Bergman film.

4. Brownsville Girl (Knocked Out Loaded, 1987)
Buried on Dylan’s worst ever album, Knocked Out Loaded, is one of his finest ever songs. Co-written with Sam Shepard, this is a widescreen western epic that is funny as shit (note how the backup singers continually undercut the narrator’s pomposity) while also being, somehow, inexplicably moving. My favorite line: “I didn’t know whether to duck or to run, so I ran.”

3. Visions of Johanna (Blonde on Blonde, 1966)
Ever wonder what it must have felt like to be stoned in a cold Greenwich Village loft circa the mid-1960s? This song will transport you. Dylan’s lyrical genius reaches its apex with the “Inside the museums” verse.

2. Idiot Wind (Blood on the Tracks, 1975)
Often described as an epic “breakup song,” I’ve always felt “Idiot Wind” was much more than that. I suspect that Dylan was thinking of his hero Woody Guthrie, for instance, in the “Down the highway” verse. In any case, the pronoun change in the final chorus (from “I” to “We”) shows an impressive humility that tempers the righteous anger on display elsewhere in the song.

1. Key West (Philosopher Pirate) (Rough and Rowdy Ways, 2020)
Dylan’s very own “Over the Rainbow,” a song about which I already wrote a mini-essay here. What else can I say? This is the final song on my deathbed playlist, the one I hope to be listening to at the exact moment my soul leaves my body.


About michaelgloversmith

Filmmaker, author and Film Studies instructor. View all posts by michaelgloversmith

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