Bob Dylan - Top 50 Songs
#50
‘To Be Alone With You’
Release Date: April 9, 1969
Album: Nashville Skyline
Nashville Skyline, a departure into country-inspired music, is not Dylan’s most critically-lauded work, but To Be Alone With You is something of a hidden gem. Perhaps George Harrison’s influence on Dylan shines through on this Beatles-like pop track.
#49
‘Obviously Five Believers’
Release Date: June 20, 1966
Album: Blonde on Blonde
#48
‘Song to Woody’
Release Date: March 19, 1962
Album: Bob Dylan
Strangely, one of Dylan’s most heartfelt love songs is addressed not to a lover but to perennial inspiration Woody Guthrie. Consider the earnestness of the lyric “I'm a-singin' you this song, but I can't sing enough/'Cause there's not many men that done the things that you've done.”
#47
‘A Simple Twist of Fate’
Release Date: January 20, 1975
Album: Blood on the Tracks
#46
‘Leopard-Skin Pill-Box Hat’
Release Date: June 20, 1966
Album: Blonde on Blonde
#45
‘Lay, Lady, Lay’
Release Date: April 9, 1969
Album: Nashville Skyline
#44
‘Quinn the Eskimo (The Mighty Quinn)’
Release Date: June 8, 1970
Album: Self Portrait
Manfred Mann recorded the iconic version of this song that demonstrates that Dylan can do simple lyrics and structures just as well as complex ones.
#43
‘I Contain Multitudes’
Release Date: June 19, 2020
Album: Rough and Rowdy Ways
Rough and Rowdy Ways has shown that Bob Dylan can still write great songs as he enters his seventh decade in the industry. The best of these is I Contain Multitudes. The advantage to an older Dylan is that he can add the depth of experience and self-reflection to his lyrics.
#42
‘Main Title Theme (Billy)’
Release Date: July 13, 1973
Album: Pat Garrett & Billy the Kid
#41
‘Outlaw Blues’
Release Date: March 22, 1965
Album: Bringing It All Back Home
#40
‘Hurricane’
Release Date: November 21, 1975
Album: Desire
#39
‘Highway 61 Revisited’
Release Date: August 30, 1965
Album: Highway 61 Revisited
#38
‘Idiot Wind’
Release Date: January 20, 1975
Album: Blood on the Tracks
Dylan letting out his spiteful side. Unforgettable, if only for Bob’s drawn-out, whiny “Iiiiiiiiiiiiiidiot wind” as he enters the chorus.
#37
‘I Shall Be Released’
Release Date: March 26, 1991 (Recorded 1967)
Album: The Bootleg Series, Volumes 1 - 3
#36
‘Sad-Eyed Lady of the Lowlands’
Release Date: June 20, 1966
Album: Blonde on Blonde
#35
‘Gates of Eden’
Release Date: March 22, 1965
Album: Bringing It All Back Home
#34
‘To Ramona’
Release Date: August 8, 1964
Album: Another side of Bob Dylan
Dylan’s sweetest lyrics and most straightforward love song. “Your cracked country lips/I still wish to kiss/As to be under the strength of your skin.”
#33
‘Ballad of a Thin Man’
Release Date: August 30, 1965
Album: Highway 61 Revisited
In which Dylan takes out his frustrations on the clueless Mr. Jones.
#32
‘Maggie’s Farm’
Release Date: March 22, 1965
Album: Bringing It All Back Home
The closest Dylan came to a traditional blues song, both in terms of harmonic structure and theme.
#31
‘If Not For You’
Release Date: October 21, 1970
Album: New Morning
Made famous by Dylan’s close friend and frequent collaborator George Harrison on his debut solo album All Things Must Pass. It’s not difficult to see why a former Beatle might see potential in this poppy, charming love song.
#30
‘Visions of Johanna’
Release Date: June 20, 1966
Album: Blonde on Blonde
#29
‘With God On Our Side’
Release Date: February 10, 1964
Album: The Times They Are A-Changin’
A historical epic set to music. Positively dripping with irony.
#28
‘It’s Alright, Ma (I’m Only Bleeding)’
Release Date: March 22, 1965
Album: Bringing It All Back Home
Apparently this is one of Dylan’s favourite songs that he wrote, and that he doesn’t consider himself capable of writing it now. Let’s be glad he wrote it when he did.
#27
‘The Lonesome Death of Hattie Carroll’
Release Date: February 10, 1964
Album: The Times They Are A-Changin’
Dylan wrote this song in a fury after hearing about black barmaid Hattie Carroll’s death as a result of a savage, racially-motivated beating from the wealthy white tobacco farmer’s son William Zantzinger in February of 1963. The sense of injustice permeates through the track.
#26
‘Man of Constant Sorrow’
Release Date: March 19, 1962
Album: Bob Dylan
#25
‘Stuck Inside of Mobile with the Memphis Blues Again’
Release Date: June 20, 1966
Album: Blonde on Blonde
A ridiculous song by any sort of standards or conventions, Stuck Inside of Mobile meanders inexorably through dense jungles of metaphor and surrealism, with Dylan flexing his lyrical muscles and creating some bizarre but truly beautiful syntactical constructions.
#24
‘Only a Pawn in their Game’
Release Date: February 10, 1964
Album: The Times They Are A-Changin’
Dylan was invited to sing Only a Pawn in their Game at the ‘March on Washington’, the major Civil Rights-era protest that also saw Martin Luther King Jr. deliver his famous “I have a dream” speech. Relentless in its lyrics, delivery and structure, it endures as one of his best protest songs.
#23
‘Tangled up in Blue’
Release Date: January 20, 1975
Album: Blood on the Tracks
The lead single from Blood on the Tracks, Tangled up in Blue is the zenith of Dylan’s ‘70s output and exemplifies his evolution as an artist while retaining elements of his earliest work.
#22
‘Masters of War’
Release Date: May 27, 1963
Album: The Freewheelin’ Bob Dylan
This song is so brutal; if I were the target of Dylan’s lyrics here I would never recover. “You ain’t worth the blood that runs in your veins.” “Even Jesus would never forgive what you do.” “All the money you made will never buy back your soul.” “And I hope that you die, and your death will come soon.” Chilling.
#21
‘Tombstone Blues’
Release Date: August 30, 1965
Album: Highway 61 Revisited
Surreal, raucous, unforgettable.
#20
‘Oxford Town’
Release Date: May 27, 1963
Album: The Freewheelin’ Bob Dylan
A fantastic example of Dylan doing a lot with so little. A heart-breaking and empowering civil rights tune.
#19
‘Knockin’ on Heaven’s Door’
Release Date: July 13, 1963
Album: Pat Garrett & Billy the Kid
Covered by Guns ‘n’ Roses in the ‘90s, Knockin’ on Heaven’s Door is the standout song of Dylan’s movie soundtrack era as he ruminates on death, regret and love. Features one of his catchiest refrains.
#18
‘In My Time of Dyin’’
Release Date: March 19, 1962
Album: Bob Dylan
In My Time of Dyin’ showcases Dylan’s arranging talent, as he takes a blues standard and transforms it into a compelling folk ballad.
#17
‘Just Like a Woman’
Release Date: June 20, 1966
Album: Blonde on Blonde
A softer cut compared to the largely sharp-edged output of this era of Dylan’s music, Just Like a Woman is a melodic, understated but nevertheless powerfully sombre song.
#16
‘Queen Jane Approximately’
Release Date: August 30, 1965
Album: Highway 61 Revisited
A B-side that outshines its A, Queen Jane Approximately is one of Dylan’s more subtle and upbeat rebuke songs, in the vein of Like a Rolling Stone.
#15
‘Positively 4th Street’
Release Date: September 7, 1965
One of Dylan’s few songs that was released as a single but never appeared on an album, Positively 4th Street juxtaposes pessimistic lyrics with feelgood folk rock. The result is a fantastic, underrated track.
#14
‘It’s All Over Now, Baby Blue’
Release Date: March 22, 1965
Album: Bringing It All Back Home
There are several things that you could draw out of this closing track from Bringing It All Back Home, but its harmonic structure deserves particular credit. The way the music oscillates between chords while feeling like it’s inexorably drawing to an inevitable conclusion marry up perfectly with the lyrical themes of decline and separation.
#13
‘A Hard Rain’s A-Gonna Fall’
Release Date: May 27, 1963
Album: The Freewheelin’ Bob Dylan
Dylan synthesises his diverse influences in perhaps the most complete way on this response to the potential nuclear annihilation of the Cuban Missile Crisis. The lyrics are influenced by Rimbaud, and structured like a traditional folk ballad. The music is pure Woody Guthrie.
#12
‘Make You Feel My Love’
Release Date: September 30, 1997
Album: Time Out Of Mind
Despite being a later addition to the Dylan canon, Make You Feel My Love has been covered by over 450 artists, most notably Billy Joel, Garth Crooks and Adele. This is testament to its artistry and to the strength of Dylan’s songwriting in general. This song is proof, if it were needed, that Dylan’s talent transcends genre and era.
#11
‘Desolation Row’
Release Date: August 30, 1965
Album: Highway 61 Revisited
Desolation Row is the closest musical equivalent to James Joyce’s Ulysses: a surreal, impermeable ode to a place and time real or imagined whose message is inscrutable but whose poetry is undeniable. It’s 11 minutes-long but I could listen to it for 11 hours.
#10
‘Mama, You Been On My Mind’
Release Date: March 26, 1991 (Recorded 1964)
Album: The Bootleg Series Volumes 1 - 3
A breakup song that, despite its numerous covers, was never formally released until 27 years after its recording, Mama, You Been On My Mind finds Dylan at his rawest and most reflective. It’s a sad, sad, gorgeous song.
#9
‘I Want You’
Release Date: June 20, 1966
Album: Blonde on Blonde
Who would have thought that an inscrutable song about guilty undertakers and lonesome organ grinders could also be one of the most compelling love songs ever made? Perhaps its the universality of the simple maxim “I want you” or the ear-worm harmonica riff but whatever formula Dylan stumbled upon for this track, it just makes you feel good.
#8
‘Mr. Tambourine Man’
Release Date: March 22, 1965
Album: Bringing It All Back Home
Fans of the Byrds’ cover version of Mr. Tambourine Man could easily mistake it for a trite, dreamy pop ballad, but hiding beneath the surface of this track is one of the most poignant tributes to the musical artform ever written. The simplicity of its refrain belies its deft evocation of the profound relationship between human expression and music-making that goes back millennia.
#7
‘Girl From the North Country’
Release Date: May 27, 1963
Album: The Freewheelin’ Bob Dylan
Clearly no one liked this tune more than Dylan himself, given that he reworked it twice more for later albums, and who can blame him? A nostalgic ballad that oozes grace and poetry, Girl From the North Country is not Dylan’s most famous love song, but it is certainly his sweetest.
#6
‘Subterranean Homesick Blues’
Release Date: March 8, 1965
Album: Bringing It All Back Home
Esoteric beat poetry set to clangorous blues guitar, listening to Subterranean Homesick Blues is like peering through a portal into a moment in history. Two minutes of pure turbulence, playfulness and meticulousness, and a bitesize masterclass in rhythm.
#5
‘All Along The Watchtower’
Release Date: December 27, 1967
Album: John Wesley Harding
Made iconic by Jimi Hendrix’s boisterous cover version, All Along The Watchtower is Dylan at his most cryptic. Perhaps it’s nonsense or perhaps its meaningful, but Dylan is always at his best lyrically when he’s hiding behind a shroud of ambiguity and metaphor, dangling meaning tantalisingly but definitively out of the listener’s reach. What can be said about the lyrics is that, whether they’re sung in Dylan’s whiny drawl or Hendrix’s playful purr, they keep you hanging on every word.
#4
‘Don’t Think Twice, It’s All Right’
Release Date: May 27, 1963
Album: The Freewheelin’ Bob Dylan
When writing about emotions and experiences, Dylan has an unrivalled knack for steering around conventionality and platitudes to arrive at an unexpected, but fiercely resonant, resolution. Never is that clearer than on Don’t Think Twice, It’s All Right. Mourning a lost relationship and enumerating its flaws, Dylan eschews regret, bitterness and despair, and instead ends up at the understated, brutally efficient, yet emotionally affecting “don’t think twice, it’s all right.” In this way, Dylan derives beauty from subtlety, made only more stirring by some of his most sensitive vocal work and a gorgeous finger-picked solo guitar instrumental.
#3
‘The Times They Are A-Changin’’
Release Date: February 10, 1964
Album: The Times They Are A-Changin’
Probably Dylan’s most overt and comprehensive protest song, The Times They Are A-Changin’ perfectly encompasses the spirit of rebellion and optimism that transcends political context and era. Unlike other protest songs, the message here is not “you are wrong” or “this needs to change”, but simply “change is gonna happen whether you like it or not, so you’d better be ready”; a sentiment that reaches straight through time and space and clutches your heart with an iron grip of vigour and resolution. Like the most famous and compelling speeches, this song makes it feel like anything is possible.
#2
‘Like a Rolling Stone’
Release Date: July 20, 1965
Album: Highway 61 Revisited
Formerly (aptly-named) Rolling Stone magazine’s number one song of all time, Like a Rolling Stone is to folk-rock music what the Odyssey is to literature, or what Citizen Kane is to film: a rhapsodic cataloguing of a person’s life that amounts to one of the standout works in its (or any) genre. After launching a fierce diatribe at his unknown subject, Dylan, as ever, asks the most pertinent question: ‘How does it feel?’ Dylan does rebuke better than any other artist, and never is it more potent than on this effervescent, raucous and hedonistic track.
#1
‘Blowin’ in the Wind’
Release Date: May 27, 1963
Album: The Freewheelin’ Bob Dylan
‘How many roads must a man walk down/before you call him a man?’ Is there a more iconic rhetorical question in the English cultural canon? Don’t answer that. As enigmatic as it is gorgeous, Blowin’ in the Wind strikes a hammer blow to the military-industrial complex in spite of, or perhaps as a result of, its simplicity. For sixty years now, artists have been grappling with its interrogative, conceptual lyrics in countless cover versions and I, for one, could listen to this song on repeat for hours. How did Dylan craft a song so simultaneously raw, ethereal, powerful and beautiful? The answer, of course, is blowing in the wind.