100. Quinn the Eskimo - Self Portrait
Manfred Mann released his version in
1968, two years before Dylan did. He
found something joyously irresistible in Dylan’s absurdist sing-along. So did the
Grateful Dead.
99. Meet Me in the
Morning - Blood on the Tracks
Dylan has always been a blues singer as much as a folk singer. Here, with the great Buddy Cage on pedal steel guitar.
98. Song to Woody - Bob Dylan
It’s hard to separate the song from the legend. The 20-year-old Bob Dylan, newly arrived in Greenwich Village, trekking out to NJ to visit his hero, the ailing Woody Guthrie, and playing for him at his bedside. Supposedly, Guthrie was impressed. Dylan came away with this tribute song, based on a Guthrie melody, “1913 Massacre.” But I can hardly listen without also hearing Dan Bern’s brilliant send-up (based on the talking blues of Dylan’s only other original song on his debut album, “Talkin New York”).
97. Working Man’s Blues #2 - Modern Times
One of the best from Dylan’s "late" period. Here he channels Merle Haggard:
Meet me at the bottom, don't lag behind
Bring me my boots and shoes
You can hang back or fight your best on the front line
Sing a little bit of these workingman's blues.
96. Rainy Day Women #12 and 35 – Blonde on Blonde
Other than “Like a Rolling Stone”,
this was the Dylan song that got the most FM radio play when I was growing up. It’s a
mad carnival of a song that invites everyone to sing along, “everybody must get stoned!”
95. Corina Corina - The Freewheelin' Bob Dylan
A traditional country blues song originally recorded by Bo Carter in 1928. One of the remarkable things about Dylan was his encyclopedic feel for America’s blues and folk traditions.
Dylan trivia: This was the first Dylan song
released by Columbia featuring a backing band.
94. Lay Lady Lay - Nashville Skyline
Of all of Dylan’s reinventions of himself, his crooning voice on Nashville Skyline may have been the most surprising. My favorite part of this song is Kenny Buttrey’s drumming on the bongos and cowbell.
93. Isis – Desire
“Isis” is supposedly based on Dylan's failing marriage, but attempting to draw conclusions about the meaning of Dylan songs has always been a risky enterprise. His live performance on Rolling Thunder Revue is riveting.
92. Highlands - Time Out of Mind
Clocking in at 16 minutes and 31
seconds, “Highlands” was Dylan’s longest song (until 2020). In a way it’s a counterpart, to “Sad Eyed Lady
of the Lowlands,” his opus recorded for Blonde on Blonde 30 years prior. It’s a meandering, hypnotic number which, like
many of his older songs, draws upon cultural figures – here, it's Robert
Burns, Charlie Patton and Neil Young.
91. Spanish Harlem Incident – Another Side of Bob Dylan
When Bruce Springsteen hit the scene,
he was hyped as “the next Dylan.” The tag never quite fit but Dylan was clearly an influence on the wordplay and imagery of Springsteen's early work. You can hear it on this Dylan verse:
Gypsy gal, the hands of Harlem
Cannot hold you to its heat
Your temperature’s too hot for taming
Your flaming feet burn up the street
And, are there any Dylan songs that the
Byrds DID’T cover?
90. I’ll Be Your Baby Tonight – John Wesley Harding
What do Bobby Darin, Linda Ronstadt,
UB40 and Norah Jones have in common? They have all covered this simple, elegant love
song.
89. Most Likely You Go Your Way and I’ll Go Mine – Blonde on Blonde
A blaring horn part is the signature
sound of this raucous number. It’s the opening track from one of my favorite live albums, Before the Flood,
with The Band.
88. You’re a Big Girl Now – Blood on the Tracks
A devastating break-up song with Dylan
howling like he means it. Check out the
live version.
87. Bob Dylan’s 115th Dream – Bringing it All Back Home
This was the revolutionary album where
Dylan went electric. On this track, he also
went surrealistic, taking us on strange journey of America with Captain Arab:
They asked me for some collateral;
and I pulled down my pants
Nice.
86. Percy's Song - Biograph
A folk song about a man tried for manslaughter, it's sad and gorgeous and featured prominently in in Don't Look Back with Joan Baez.
85. The Man in Me – New Morning
Three words. The Big Lebowski.
84. Only a Pawn in Their Game - The Times they Are-a-Changing
Listening to the politically charged
folk songs from Dylan’s early career, we can marvel at his sharp eye and power as a writer. But with
hindsight, we can also appreciate how the constraints of the genre and the expectations of its purist followers would become an artistic straight
jacket.
83. I’m Not There – I’m Not There, Soundtrack
One of the best things about the 2007
film, I’m Not There, was the release of the haunting title track, which
was recorded 40 years earlier in the session for the Basement Tapes.
82. 4th time Around – Blonde on Blonde
Don’t waste time trying to figure out
whether this song is an homage to John Lennon’s “Norwegian Wood” or a parody
of the same. It’s both and neither. This is Bob Dylan we’re talking about.
81. If You See Her Say Hello – Blood on the Tracks
A gut-wrenching break-up song, but
without his usual barbs and kiss-offs.
Just sadness.
80. Romance in Durango - Desire
The outlaw-on-the-run genre has always been a favorite. I love the live version from Rolling Thunder Revue.
79. Gates of Eden – Bringing it All Back Home
Powerful imagery here – abstract and
mysterious. His poetry is captivating
but also the stuff of nightmares.
78. Going Going Gone - Planet Waves
Planet Waves is in the running for Dylan’s most underrated album. It’s also the only official studio album release that features the Band. To appreciate why the Band was so perfect for accompanying Dylan, just listen to interplay between Dylan’s voice and Robbie Robertson’s guitar on this track. And check out the haunting alternate take – a rebuke to anyone who tells you that Bob Dylan can’t sing.
77.
As it happens, US Highway 61 cuts right through America, running from Minnesota to New Orleans. Dylan mines that highway, exposing us to all manner of characters, sins and musical traditions along the way. And that damn siren whistle.
76. Leopard Skin Pill Box Hat – Blonde on Blonde
The leopard-skin pill box hat is to
Dylan what the coffee-colored Cadillac is to Chuck Berry: an anachronism made
immortal though rock & roll poetry. A rollicking number, Dylan is sneering,
snarling and playful all at once.
75. Series of Dreams – Bootleg Series Vol. 1-3
Bob Dylan has a cult following of fans who've argued for years about his best unreleased tracks. One of my favorites is "Series of Dreams” which was recorded for Oh Mercy in 1989. If it sounds like a U2 song, that’s the layered production of Daniel Lanois.
74. This Dream of You – Together Through Life
Yet another dream song and gorgeous
gem from Dylan’s “late” period.
73. I Dreamed I Saw St. Augustine – John Wesley Harding
An enigmatic and evocative mediation
of spirituality and guilt. How many Bob
Dylan songs have the word “dream” in the title? Dreams are to Bob Dylan what Love was to the
Beatles.
72. To Ramona – Another Side of Bob Dylan
Dylan was pushing musical boundaries
even before he went electric. Here he delivers a lovely Mexican folk tune in
waltz-time. It’s one of my favorites of
his vocal performances.
71. Tombstone Blues – Highway 61 Revisited
We meet the ghost of Belle Starr, the King of the Philistines. John the Baptist and Paul Revere’s horse. Just a dazzling set of images, allusions and absurdity with Michael Bloomfield adding some of his tastiest guitar licks.
70. All I Really Want to Do – Another Side of Bob Dylan
The Byrds version is very good but it lacks Dylan’s sense of irony and play. Hear him giggle like a stoner.
69. Moonlight - Love and Theft
Beneath Dylan’s croaking voice is a
romantic song that could have been a Tin Pan Alley classic 100 years
ago.
68. When I Paint My Masterpiece – Greatest Hits Vol. II
For some listeners, Dylan’s voice is
acquired taste. Others will never get
there. I love the sound of his voice on
this track, especially the ragged howl he delivers live on Rock of Ages
with the Band.
67. One Too Many Mornings – The Times they are-a-Changing
A lovely acoustic number that was
given fresh bite when Dylan went electric in 1966.
66. Love Sick – Time Out of Mind
Yeah, the Victoria Secret commercial
was creepy. But this is one helluva
song.
65. One of us Must Know (Sooner or Later) – Blonde and Blonde
This entire list could be retitled:
“the top 84 songs by Bob Dylan plus Blonde on Blonde."
64. Hurricane – Desire
Let’s get this part of the way. The story Dylan tells of imprisoned boxer Ruben “Hurricane” Carter – is not entirely accurate. But a good writer does not let the facts get in the way of the truth. What stands out here is the way Dylan takes a folk music staple, the topical protest song, and infuses it with a rock and roll heart.
63. Nettie Moore – Modern Times
Another song of lost love that, like Dylan’s best offerings, seems to transcend musical genre and time itself:
I'll be drifting along
The woman I'm loving she rules my heart
No knife could ever cut our love apart
62. Lily, Rosemary and The Jack of Hearts – Blood on the Tracks
Another outlaw song. I’m such a sucker for these sprawling, cinematic country epics.
61. Boots of Spanish Leather - The Times they Are-a-Changin'
A captivating and heartbreaking
finger-picking ballad that feels like a continuation of “Girl from the North
Country.”
60. This Wheel’s on Fire – The Basement Tapes
One the gems that emerged from the Big
Pink, the house where Dylan and the Band lived and recorded in 1967.
59. You’re Gonna Make Me Lonesome When You Go – Blood on the Tracks
Blood on the Tracks is
often regarded as Dylan’s “break-up” album.
But whether these songs of heartbreak are rooted in his personal
experience, in poetry or his imagination, makes no difference to me. I love the
way he howls on the live version.
58. It Takes a Lot to Laugh, it Takes a Train to Cry – Highway 61 Revisited
Dylan reinvents the blues on this album with a laid-back groove, ghostly Hammond organ, barrelhouse piano,
raunchy harmonica and Bloomfield guitar licks, a sound that would transform pop
music.
57. Tonight I’ll be Staying Here with You – Nashville Skyline
This love song is a highlight of
Dylan’s underrated country phase. It’s
another song that turns raucous when played live and Dylan’s voice has rarely
sounded better than when he belted it out on the Rolling Thunder tour.
56. If Not for You – New Morning
A catchy love song that was also released by George Harrison.
Trivia: The
bass player for the New York City recording session in 1970 was Charlie
Daniels.
55. Brownsville Girl – Knocked out Loaded
Co-written with Sam Shepard, "Brownsville Girl" is another sprawling cinematic outlaw ballad that once again takes us 'cross the border to Mexico.
54. Make You Feel My Love – Time Out of Mind
Yeah, it’s everywhere. Popular at weddings and covered by everyone. It might even be more widely covered than Leonard Cohen’s Hallelujah.
Trivia:
Billy Joel’s version was the first ever to be released.
53. Masters of War - The Freewheelin' Bob Dylan
The 1960s protest singer is something
of cliché. But every once in a while,
you hear a song with such power and bite, it makes you say, “Damn, how does a
21-year-old write that.”
52. Most of the Time – Oh Mercy
Oh Mercy, recorded in New Orleans and produced by Daniel Lanois, is also in the running for Dylan’s most underrated album. This song was featured to great effect in the film adaptation of High Fidelity.
51. Things Have Changed – Wonder Boys, Soundtrack
Speaking of movies, Dylan wrote and
recorded this one in 1999 for the excellent Curtis Hanson film, Wonder Boys.
Rolling Stone magazine described this
song as the evil twin of “the Times they Are-a-Changin'.”
People are crazy and times are strange
I'm locked in tight, I'm out of range
I used to care, but things have changed
50. You Ain’t Goin Nowhere – The Basement Tapes
The Byrd’s version, from Sweetheart of the Rodeo, is different from the early Byrds covers of Dylan songs. The early Byrds were all about jangle and harmony. With the Byrds of Gram Parsons, you get the rhythm and twang of country rock. But with Dylan and the Band, its Americana.
49. Queen Jane Approximately – Highway 61 Revisited
The banging piano, Dylan’s thin nasally voice, the richness of the organ and Bloomfield’s guitar licks. Check out a great version by Lucinda Williams.
48. Love Minus Zero No Limit – Bringing it All Back Home
Pure poetry here.
The night blows cold and rainy,
My love she's like some raven
At my window with a broken wing
47. Forever Young – Planet Waves
The best writers flirt with sentimentality
but don't cross the line into mawkishness. “Forever Young” comes close but
Dylan stops short by keeping it simple and from the
heart.
May you build a ladder to the stars
And climb on every rung
And may you stay
Forever Young.
46. I Shall Be Released – Greatest Hits, Vol. II
A simple spiritual song and one of
Dylan’s most-covered compositions. For
my money, the Band’s version with Richard Manuel’s fragile falsetto is the best
version.
45. Changing of the Guards - Street Legal
Bob Dylan doesn’t get enough credit
for his output in the late 1970s and 80s but it’s partly his own fault - he set
the bar too damn high. Street Legal was
the last album before his born-again phase and “Changing of the Guards” is the
anthemic highlight. If anyone else had
released this song, they’d be saying “Check this guy out – he’s the next
Dylan.”
44. Girl from the North Country - The Freewheelin' Bob Dylan
A ballad that feels older than time. Dylan re-recorded it as a duet with Johnny Cash on Nashville Skyline.
43. Jokerman – Infidels
My first exposure to this song was the
MTV video. Although I loved Dylan's famous songs of the 1960s, when I was a teenager, I saw him as more of a historical figure. But there he was on my television, and I was utterly captivated by
the imagery of the song and sound of Dylan’s voice.
42. Murder Most Foul – Rough and Rowdy Ways
I found myself wondering: Why would Bob Dylan release a song in 2020 about the assassination of JFK? Then I listened and was transfixed for the full 16 minutes. Of course, its’s not just a song about the assassination. It’s about America and what we lost.
41. Sad Eyed Lady of the Lowlands – Blonde on Blonde
Dylan’s 11 minute opus is haunting, hypnotic and mysterious. It was also pretty radical, in 1966, to devote an entire album side (side four) to a single song.
40. Maggie’s Farm – Bringing it all Back Home
When Dylan went electric at the 1965
Newport Folk Festival, “Maggie’s Farm” was one of the songs whose aggressive
sound shocked and awed the audience. But
the anger and disillusionment were already present in the lyrics:
But everybody wants you to be just like them
A perfect anthem for the 1960s counterculture.
39. Lonesome Death of Hattie Carroll - The Times they Are-a-Changing
Most protest songs are preachy and humorless. And the catch is -- the more topical they are, the less likely they are to age well. But as with most things Dylan, “Lonesome Death of Hattie Carroll” is different. He taps into themes of injustice and loss and freedom that are universal. And he also brings the gift of melody.
38. Knocking on Heavens Door - Pat Garrett & Billy the Kid
Dylan’s version is more powerful than
Clapton’s or the bloated Guns ‘n’ Roses version. Just a lone man on the frontier, at the edge,
facing the end.
37. I Threw it All Away – Nashville Skyline
A simple, timeless and gut-wrenching
lament of lost love and regret.
36. Abandoned Love - Biograph
This magnificent track, recorded in 1975, was somehow left off of Desire. A breakup song with unforgettable lyrics:
My patron saint is a-fighting with a ghost
He's always off somewhere when I need him most
The Spanish moon is rising on the hill
But my heart is a-tellin' me I love you still
35. I Want You – Blonde on Blonde
The characters and imagery are irresistible:
The gypsy undertaker cries
The lonesome organ grinder sighs
The silver saxophones say I should refuse you
The cracked bells and washed-out horns
Blow into my face with scorn
But it's not that way
I wasn't born to lose you
34. Chimes of Freedom – Another Side of Bob Dylan
“Chimes of Freedom” is an anthem for
the downtrodden or, as Andy Gill calls it, “Dylan’s Sermon on the Mount.” When
the Byrds play the song, it sparkles but it sounds like a relic of the 1960s. When Dylan sings, it seems to transcend time.
33. Can You Please Crawl Out Your Window – Masterpieces
Recorded for the Highway 61 Revisited
session, Dylan’s voice is clear and confident and the piano, organ and Dylan’s
harmonica mesh perfectly. It was an
interesting selection by Nick Hornby in his wonderful collection of essays, Songbook. The Hold Steady did a delightful version.
32. Baby Let Me Follow You Down – Bob Dylan
Another gentle acoustic number that
was radically transformed when Dylan went electric. His raucous, almost punk rock version with
the Band is one of the highlights of The Bootleg Series, Vol. 4. The Royal
Albert Hall Concert.
31. Not Dark Yet – Time Out of Mind
Bob’s striking musing on death (“It’s
not dark yet, but it’s getting there”) was released 24 years ago when he
was 56. Damn.
30. Ring Them Bells – Oh Mercy
A powerful ballad that draws upon
biblical texts. Dylan’s religious
conversions were often the subject of attention, but wherever his journeys took him, he always
had the voice of an Old Testament prophet.
29. Up to Me – Biograph
Even before the release of Biograph,
“Up to Me”, which was recorded for Blood on the Tracks was a popular
choice among Dylan fanatics and bootleggers for the best song never
released. One listen and you’ll
understand why:
Everything went from bad to worse, money never changed a thing
Death kept followin', trackin' us down, at least I heard your bluebird sing
Now somebody's got to show their hand, time is an enemy
I know you're long gone
I guess it must be up to me
28. Every Grain of Sand – Shot of Love
Maybe it’s because I’m not a religious
believer. But for me, a song like this has greater spiritual power than any
holy book or revelation.
27. Buckets of Rain – Blood on the Tracks
Such a sweet song.
Friends will arrive, friends will disappear
If you want me Honey baby, I'll be here
26. Blind Willie McTell - Bootleg Series Vol. 1-3
You hear about these songs - the
unreleased tracks that fans gush over, and you think: these hardcore
fans are just trying to sound cool – there’s
probably a good reason they left the track off the album. Not here.
This is brilliant.
25. Just Like Tom Thumb Blues – Highway 61 Revisited
Some of Dylan’s most captivating
lyrics, starting with the memorable opener which just transports me:
When you're lost in the rain in Juarez, when it's Easter time too.
And I've always loved the last verse:
I started out on burgundy, but soon hit the harder stuff
Everybody said they'd stand behind me when the game got rough
But the joke was on me, there was nobody even there to bluff
I'm goin' back to New York City, I do believe I've had enough.
24. It Ain’t Me Babe – Another Side of Bob Dylan
The ultimate it's not you, it's me (really, it's you) song. I’m a fan of the version by the Turtles too.
23. Absolutely Sweet Marie – Blonde on Blonde
So many great lyrics, and none better
than: to live outside the law you must be honest. I love the version by
cowpunk pioneers, Jason & the Scorchers.
22. Ballad of Thin Man – Highway 61 Revisited
The pounding piano, Al Kooper’s ghostly
organ and Dylan’s sneering delivery make for a foreboding and unforgettable
kiss-off.
21. Subterranean Homesick Blues – Bringing it all Back Home
No, it’s not the first rap song. It’s part Chuck Berry and part talking blues, the kind of songs that were a staple of Dylan’s early recordings. The result, Dylan’s first real electric
number, was revolutionary. And the D.A.
Pennebaker video is, arguably, the most influential music video of all time.
20. Don’t Think Twice - The Freewheelin' Bob Dylan
A lovely breakup song. Eric Clapton's version at the Dylan 30th anniversary concert in Madison Square Garden, New York is worth a listen.
19. My Back Pages – Another Side of Bob Dylan
The refrain alone (I was so much
older then, I’m younger than that now) justifies a top 20 ranking. As good as the track is, it’s one of the few Dylan songs where I prefer the Byrd’s version The star-studded ensemble performance was the highlight of the 30th anniversary concert.
18. Stuck Inside of Mobile with the Memphis Blues Again – Blonde on Blonde
In 2009, I saw Dylan play at the United Palace Theater in Washington Heights and he opened with this classic. I love his vocal delivery and the way he moans: “Oh, mama, can this really be the end” and that sensual sneer: "Your debutante just knows what you need But I know what you want.”
17. It’s Alright Ma - Bringing it All Back Home
There’s a fury in this track, an assault on power, propaganda and illusion with unforgettable lines like “He not busy being born is busy dying.”
16. Simple Twist of Fate – Blood on the Tracks
A lovely song of melancholy and depth. Hard to top this verse:
People tell me it’s a sin
To know and feel too much within.
I still believe she was my twin, but I lost the ring.
She was born in spring, but I was born too late
Blame it on a simple twist of fate.
15. Just Like a Woman – Blonde on Blonde
Probably, Dylan’s greatest love
song. I love his phrasing in the bridge
and the passion with which he launches into the final verse.
And your long-time curse hurts, but what's worse
Is this pain in here, I can't stay in here, ain't it clear….that I… just can’t fit.
14. It’s All Over Now Baby Blue – Bringing it All Back Home
Dylan’s farewell to someone, or something – or to everything – comes at a pivotal moment of his artistic transition. He is ever ready to move ahead.
Strike another match, go start anew. And it’s all over now, Baby Blue.
13. Shelter from the Storm – Blood on the Tracks
One of the many highlights of Blood on the Tracks, an album that captures so many emotions and brilliant lyrics, like this gem: Beauty walks a razor's edge, someday I'll make it mine. It's a song that was brilliantly transformed in his 1970s live performances.
12. Mississippi – Love and Theft
Some of Dylan’s songs seem like they have always existed in the universe and the songwriter’s job was simply to reveal them. “Mississippi” is like that. The voice of a seeker, full of wisdom and regret. It feels timeless.
11. All Along the Watchtower – John Wesley Harding
Give Jimi Hendrix credit for
transforming the song and bringing ungodly firepower. But Dylan’s creation is a
masterwork in its own right, a truly unique song, with powerful imagery and a
chilling, foreboding feel.
10. Idiot Wind – Blood on the Tracks
Dylan is a master of the “fuck you”
song. Most of his kiss-offs tend to be
sly, ironic and punctuated with well-timed sneers. “Idiot Wind" is different because it’s so
raw. Dylan wears his contempt on his
sleeve or, to put it another way, his blood on the tracks.
9. Mr. Tambourine Man – Bringing it All Back Home
Overlooked in the jangle of the Byrd’s
first #1 hit is the revolutionary nature of Dylan’s song writing. There was simply
nothing like this on the radio. It
evokes such powerful sense of longing.
8. Positively 4th Street – Greatest Hits
Probably the very best of Dylan’s “fuck you” songs. I’m not counting “Like a Rolling Stone” which belongs in its own category.
7. Blowin’ in the Wind - The Freewheelin' Bob Dylan
Perhaps his most famous song. “Blowin’ in the Wind” was recently named the
2nd most essential folk song of all time, after Woody Guthrie’s
“This Land is Your Land.”
6. Desolation Row – Highway 61 Revisited
A literary narrative with a dizzying
display of imagery but what really stands out for me is the Spanish-sounding
guitar part by Charlie McCoy.
5. Visions of Johanna – Blonde on Blonde
A favorite among those who celebrate
Dylan’s poetry. But the reason it’s the best song on one of the greatest albums
in rock history, isn’t only because of the lyrics. It’s the groove. The throbbing bass by Joe South and Nashville
session man, Kenny Buttrey on drums. Just perfect.
4. The Times they Are a-Changin - The Times they Are-a-Changing
Out of all of Dylan’s protest songs, this is the one that still gives me chills. If there is a single song that cements Dylan place as the “voice of a generation,” this one gets my vote. The voice of a prophet.
3. Tangled up in Blue – Blood on the Tracks
I’ve always loved the feel of this
song. Even before Dylan starts singing, the
listener is transported to some ethereal once-upon-a-time place. For me, this song feels like the farewell to
the 1960s and its dreams.
2. Hard Rain’s Gonna Fall - The Freewheelin' Bob Dylan
This song never fails to blow my mind. It’s hard to imagine what it must have been like to be living in New York in 1962 and hearing Dylan for the first time. According to Joyce Carol Oates, “When we first heard this raw, very young, and seemingly untrained voice, frankly, nasal, as if sandpaper could sing, the effect was dramatic and electrifying.” There’s a great scene at the end of the Coen Brothers, Inside Llewyn Davis, where we see the young Dylan performing at the Gaslight Cafe and we understand that the title character, a struggling folk singer, is about to be eclipsed by an artist of real genius.
1. Like a Rolling Stone – Highway 61 Revisited
When Bruce Springsteen inducted Dylan
into the Rock and Roll Hall of Fame, he described the opening of this song as “That
snare shot that sounded like somebody kicked open the door to your mind.” It thrills me every time I hear it.
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