Looking back at my favorite Bob Dylan songs
For me, all roads lead to and from Bob Dylan.
Those three artists are among my favorite bands and musicians, as well as being among the many acts who have covered a Bob Dylan song. The musical footprint of Dylan — who bursted onto the musical stage during the folk revival movement of the 1960s — is epic in scale. He changed music in its presentation (how to be a “rockstar”) but also gave his audiences a deeper connection with the music he performed.
Dylan mastered the folk music traditions of storytelling and then amplified those traditions to create masterpieces with a message. He was not singing to become a star; Dylan had something to say.
I came to Dylan after some convincing. Growing up as a kid, I was unfamiliar with his music. In middle school, I gave him a shot and did not like what I was hearing. His voice was unbearable; I did not quite connect with the 8 to 9 to 10 minute songs. They seemed to ramble on about random things I knew nothing about. The music was not for me.
Then, in high school, I looked at his music in a different light. Thanks to my sophomore English teacher, our class listened to various songs — two of which were from Bob Dylan and both are on this list — and broke down the lyrics and their possible meanings. For me, Dylan’s was the most interesting. In his songs, I realized he always came across the best word/phrase to deliver the strongest meaning. His musical flow and rhythms could make any modern hip-hop artists jealous. Most importantly: he was telling stories straight from the human soul.
From there it was as if sledding downhill with no brakes or end in sight. The mass amount of output was daunting, but I dove in excitingly. I soon realized Dylan was everywhere in history. He covered songs from the 1700s, wrote new songs that were being popularized by modern musicians and was still churning out new songs. His contribution to modern music was unmistakable. Yet, he was also bringing attention to the musical traditions of a time gone by. I was hooked.
Ever since, Dylan has been at the center of my musical tastes. His lyrics are words of wisdom, humor and curiosity. There are fun songs to sing along with but also songs that question society. The songs are talking points for its listeners, observations on historic events and surreal dives into the human psyche.
This past week, Bob Dylan released a 16 minute song that covers the themes and styles the singer-songwriter has been known for ever since the 1960s. To celebrate, I went back to deep dive and pulled together my 75 favorite songs (and absolute must listens) for those wondering about what makes Dylan so great.
I included lyrics that have stood out to me, versions that beckon for a listener and a playlist that includes every song on this list (in descending order). The playlist can be found on Spotify here.
What are your go to Dylan tracks? Here are mine:
75. “Pay in Blood” from ‘Tempest’ (2012)
The last good, new Dylan album. The punchy music and biting lyrics are a reminder of why Dylan is the best.
How I made it back home nobody knows
Or how I survived so many blows
I been through hell, what good did it do?
My conscience is clear, what about you?
74. “Señor (Tales of Yankee Power)” from ‘Street Legal’ (1978)
A punchy chorus and a folk-y story go hand in hand.
This place don’t make sense to me no more
Can you tell me what we’re waiting for, señor?
73. “Bound to Lose, Bound to Win” from ‘The Bootleg Series, Vol 9: The Witmark Demos: 1962–1964' (2010)
The beginnings of a song, a damn fine melodic one at that. My first deep dive in Dylan bootlegs. Sometimes these half-songs really have no deeper meaning; sometimes they are just catchy as hell.
72. “Drifter’s Escape” from ‘John Wesley Harding’ (1968)
The stories Dylan tells in his stories are not just protest anthems, but mystic folklore that highlights something strange about the American experience.
Just then a bolt of lightning
Struck the courthouse out of shape
And while ev’rybody knelt to pray
The drifter did escape
71. “Positively 4th Street” a B-side from the single ‘Like a Buick 6' (1965)
A running theme within Dylan’s music is mystery. Who or where Dylan is talking about in this song remains unknown, helping the listener put themselves in Dylan’s place. Whoever Dylan is reflecting about, he is not reflecting happy memories.
You see me on the street
You always act surprised
You say, “How are you?”, “Good luck”
But you don’t mean it
70. “Where Teardrops Falls” from ‘Oh Mercy’ (1989)
You know the song in my heart
In the turning of twilight
In the shadows of moonlight
You can show me a new place to start
69. “Gypsy Lou” from ‘The Bootleg Series, Vol 9: The Witmark Demos: 1962–1964’ (2010)
68. “I Shall Be Free” from ‘The Freewheelin’ Bob Dylan’ (1963)
Another theme in Dylan’s music is the tradition of folk music. This song is based on a LeadBelly song “We Shall Be Free”. This song closes the album released in the folk revival movement of the 1960s and represents artists taking melodies and lyrics and, usually, re-working them to fit the modern age.
Now, the man on the stand he wants my vote
He’s a-runnin’ for office on the ballot note
He’s out there preachin’ in front of the steeple
Tellin’ me he loves all kinds-a people
(He’s eatin’ bagels
He’s eatin’ pizza
He’s eatin’ chitlins
He’s eatin’ bullshit!)
Dylan did this quite a lot, which cemented him as a folk hero. Folk music has always been about sharing a message, and no one really embodies that tradition more so than Bob Dylan. There are more examples to come.
67. “Sara” from ‘Desire’ (1976)
A love song to his then wife, Sara, which Dylan recorded while she was present at the session.
66. “All Along the Watchtower” from ‘John Wesley Harding’ (1968)
Though I heard the Jimi Hendrix version first, the song is an example of my musical taste always lead me to Bob Dylan.
65. “Neighborhood Bully” from ‘Infidels’ (1983)
He got no allies to really speak of
What he gets he must pay for, he don’t get it out of love
He buys obsolete weapons and he won’t be denied
But no one sends flesh and blood to fight by his side
He’s the neighborhood bully
64. “Long Pilgrim” from ‘World Gone Wrong’ (1993)
In the early 1990s, Dylan moved away from full on bands and complex arrangements. He went back to simple folk music. World Gone Wrong was the second album of the 1990s that featured Dylan, folk tunes, a guitar and the occasional harmonica — the things that made him famous.
A more rugged voice and dark song choices leave this album much more darker; its best is “Lone Pilgrim”.
63. “Little Maggie” from ‘Good as I Been to You’ (1992)
The first (and more enjoyable) return to folk music for Dylan. There are a ton of sweet tunes on this album — an underrated album — and “Little Maggie” is the tips of this iceberg.
62. “Man of Constant Sorrow” from ‘Bob Dylan’ (1962)
Dylan’s take on a folk music staple from the early 1900s.
61. “Like a Rolling Stone” from ‘Highway 61 Revisited’ (1965)
When you got nothing, you got nothing to lose
You’re invisible now, you got no secrets to conceal
60. “Walkin’ Down the Line” from ‘The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991’ (1991)
59. “All over You” from ‘The Bootleg Series, Vol 9: The Witmark Demos: 1962–1964’ (2010)
Though Dylan is known for his longer, epic songs, sprinkled in his music repertoire are fun, light and catchy songs about love, friendship and everything in-between.
58. “Nettie Moore” from ‘Modern Times’ (2006)
57. “Man in the Long Black Coat” from ‘Oh Mercy’ (1989)
A popular folk song story is the “demon lover” — songs like “House Carpenter” — where a woman is whisked away from her mortal lover and falls in love with a demon. Dylan took that story and turned it upside down. This slick, moody and quiet song gives a deeper perspective of the demon and not the mortal lover. It is a haunting and fascinating look at love.
There are no mistakes in life some people say
And it’s true sometimes you can see it that way
I went down to the river but I just missed the boat
She went with the man/In the long black coat
56. “Main Title Theme (Billy)” from ‘Pat Garrett & Billy the Kid’ (1973)
A soundtrack for the movie Pat Garrett & Billy the Kid where most people jam out to Knockin’ on Heavens Door. But the main title is some of the most contemplative and beautiful music I’ve heard.
55. “Changing of the Guards” from from ‘Street Legal’ (1978)
54. “Mixed-Up Confusion” from ‘Biograph’ (1968)
I got mixed up confusion
Man, it’s a-killin’ me
Well, there’s too many people
And they’re all too hard to please
53. “Blowin’ in the Wind” from ‘The Freewheelin’ Bob Dylan’ (1963)
This is a staple among many Dylan fans and fans of the folk revival of the 1960s. The song’s lyrics are a series of rhetorical questions; the genius stems from the song being relevant throughout the years since its release. Though, the mystery that surrounds many Dylan songs even relate to the popular ones.
When asked what the song was about in a 1962 interview in Sing Out!, Dylan replied, “There ain’t too much I can say about this song except that the answer is blowing in the wind.”
52. “I Dreamed I Saw St. Augustine” from ‘John Wesley Harding’ (1968)
51. “Political World” from ‘Oh Mercy’ (1989)
We live in a political world
Where peace is not welcome at all
It’s turned away from the door to wander some more
Or put up against the wall
Still as relevant today as it was in 1989.
50. “Jokerman” from ‘Infidels’ (1983)
49. “It’s All Over Now, Baby Blue” from ‘Bringing It All Back Home’ (1965)
Forget the dead you’ve left, they will not follow you
The vagabond who’s rapping at your door
Is standing in the clothes that you once wore
Strike another match, go start anew
And it’s all over now, Baby Blue
48. “All I Really Want to Do” from ‘Another Side of Bob Dylan’ (1964)
Often over-looked are pleas for friendship or of loneliness. Audiences respond to songs about love and hate because, usually, those are songs where the passion really resonates. But, songs like this, helped by Dylan’s incredible ability to choose the perfect word, are much more meaningful. His plea for someone to notice him or acknowledge him is quite painful, yet powerful.
I don’t want to fake you out
Take or shake or forsake you out
I ain’t lookin’ for you to feel like me
See like me or be like me
All I really want to do
Is, baby, be friends with you
47. “With God on Our Side” from ‘The Times They a-Changing’ (1964)
46. “Blind Willie McTell” from ‘The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991’ (1991)
Dylan singing about a blues artist from the early 1900s, where he sings, “No one can sing the blues like Blind Willie McTell”. It makes one curious about who is McTell and is his music that powerful. (Yes, yes it is.)
45. “Baby, I’m Mood In the Mood for You” from ‘The Bootleg Series, Vol 9: The Witmark Demos: 1962–1964’ (2010)
Sometimes I’m in the mood, I wanna change my house around
Sometimes I’m in the mood, I’m gonna make a change in this here town
Sometimes I’m in the mood, I’m gonna change the world around
But then again, but then again, I said oh, I said oh, I said
Oh babe, I’m in the mood for you
44. “Step It up and Go” from ‘Good as I Been to You’ (1992)
One of the more livelier tunes from Dylan is a cover of a standard blues tune from the 1930s. This song features some of Dylan’s best guitar strumming.
Got a little girl, little and low,
She used to love me but she don’t no more.
She gotta step it up and go-Yeah, go.
Can’t stand pat, swear you gotta step it up and go.
43. “Simple Twist of Fate” from ‘Blood on the Tracks’ (1975)
42. “Only a Pawn in Their Game” from ‘The Times They a-Changing’ (1964)
Dylan’s song about the assassination of Civil Rights leader Medger Evers. Powerful with an confusion and anger that Dylan beautifully captures. Here he is performing the song during the March on Washington:
41. “It Ain’t Me Babe” from ‘Another Side of Bob Dylan’ (1964)
Probably as blunt as Dylan can get and that bluntness is its power. A track that has been covered many times over, but Dylan’s version remains its most genuine.
You say you’re lookin’ for someone
Who will promise never to part
Someone to close his eyes for you
Someone to close his heart
Someone who will die for you an’ more
But it ain’t me, babe
40. “I and I” from ‘Infidels’ (1983)
39. “Everything Is Broken” from ‘Oh Mercy’ (1989)
A song about life falling apart. Nothing too deep but its effective.
Every time you leave and go off someplace
Things fall to pieces in my face
38. “Whatcha Gonna Do?” from ‘The Bootleg Series, Vol 9: The Witmark Demos: 1962–1964’ (2010)
Tell me what you’re gonna do
When you can’t play God no more?
37. “To Be Alone With You” from ‘Nashville Skyline’ (1969)
A sweet tune and one where Dylan’s voice (and music) begins to shift.
To be alone with you
At the close of the day
With only you in view
While evening slips away
It only goes to show
That while life’s pleasures be few
The only one I know
Is when I’m alone with you
36. “Honey, Just Allow Me One More Chance” from ‘The Freewheelin’ Bob Dylan’ (1963)
35. “If You See Her, Say Hello” from ‘Blood on the Tracks’ (1975)
34. “Thunder on the Mountain” from ‘Modern Times’ (2006)
A song that conjures up the melodies and vibe of rock-a-billy. It is a fun song that features a shoutout to Alicia Keys. What more do you want from Bob Dylan!?
Well, there’s hot stuff here and it’s everywhere I go
I was thinkin’ ‘bout Alicia Keys, couldn’t keep from crying
When she was born in Hell’s Kitchen, I was living down the line
I’m wondering where in the world Alicia Keys could be
33. “Mr. Tambourine Man” from ‘Bringing It All Back Home’ (1965)
32. “Ring Them Bells” from ‘Oh Mercy’ (1989)
This album was coming off of Dylan’s dive into religious albums. Spirituals and religious themes run all over folk music — usually fitted in a way to fit the message of the day. By 1989, Dylan was more introspective and writing about human connections that songs with strong protesting lyrics. Coupled with a gorgeous piano, “Ring Them Bells” is the shinning light from an underrated album.
Ring them bells for the blind and the deaf
Ring them bells for all of us who are left
Ring them bells for the chosen few
Who will judge the many when the game is through
31. “John Wesley Harding” from ‘John Wesley Harding’ (1968)
A western tale about an outlaw — whose actual name was John Wesley Hardin.
30. “Tombstone Blues” from ‘Highway 61 Revisited’ (1965)
While there are plenty examples of Dylan’s lyrics packing tons of emotional weight, he has delved into the world of the surreal. Sometimes the words are meaningless — or so they seem. Do we give them meaning when searching for meaning? Or should we just sing along and enjoy?
Well, John the Baptist after torturing a thief
Looks up at his hero the Commander-in-Chief
Saying, “Tell me great hero, but please make it brief
Is there a hole for me to get sick in?”
29. “Canadee-I-O” from ‘Good as I Been to You’ (1992)
28. “Mozambique” from ‘Desire’ (1976)
According to legend, this song was written to see how many times Dylan could rhyme “ique”.
27. “Girl from the North Country” from ‘The Freewheelin’ Bob Dylan’ (1963)
No one captures the pain, sadness and loneliness of lost love like Bob Dylan.
So if you’re travelin’ in the north country fair
Where the winds hit heavy on the borderline
Remember me to one who lives there
She once was a true love of mine
26. “The Times They Are A-Changing” from ‘The Times They a-Changing’ (1964)
25. “Gates of Eden” from ‘Bringing It All Back Home’ (1965)
The epic of poetry of Bob Dylan in full force, as well as his surreal writing powers in full effect. Dylan has described the song as a “love song”. Looking for what is being loved and by whom will have one listening on repeat.
The kingdoms of Experience
In the precious wind they rot
While paupers change possessions
Each one wishing for what the other has got
And the princess and the prince
Discuss what’s real and what is not
It doesn’t matter inside the Gates of Eden
24. “Subterranean Homesick Blues” from ‘Bringing It All Back Home’ (1965)
One of the few songs that started getting myself to look at Dylan more closely. Its iconic video, incredible vocal performance and Dylan’s genius at constructing sentences are all on display. Always remember: “You don’t need a weatherman to know which way the wind blows”.
23. “Spanish Harlem Incident” from ‘Another Side of Bob Dylan’ (1964)
22. “Tangled up in Blue” from ‘Blood on the Tracks’ (1975)
But all the while I was alone
The past was close behind
I seen a lot of women
But she never escaped my mind, and I just grew
21. “John Brown” from ‘The Bootleg Series, Vol 9: The Witmark Demos: 1962–1964’ (2010)
This song should be higher. If I was listing songs on importance, it would make the top 5. When I was really looking for songs to really dive into, I saw “John Brown” and immediately thought the song was about the infamous radical American who tried to start a race war in the 1850s. It’s not.
The anti-war song is about a mother not wanting her son to go to war. The song and its subject matter is a mainstay in the folk movement. Listening to its story and reading about its history, I was hooked.
20. “What Good Am I?” from ‘Oh Mercy’ (1989)
19. “The Man in Me” from ‘New Morning’ (1970)
The man in me will hide sometimes to keep from bein’ seen
But that’s just because he doesn’t want to turn into some machine
Took a woman like you
To get through to the man in me
18. “Diamond Joe” from ‘Good as I Been to You’ (1992)
17. “Desolation Row” from ‘Highway 61 Revisited’ (1965)
Ambitious, long and filled with imagery and lyrics most artists envy about, “Desolation Row” is Dylan flexing his skills. Lyrics are meant to be relatable and tell a story (or describe a feeling), where the listener can connect with the artist. Dylan does that 100x over. He paints imagery without much effort — or so it seems.
Now the moon is almost hidden; the stars are beginning to hide
The fortune-telling lady has even taken all her things inside
All except for Cain and Abel and the hunchback of Notre Dame
Everybody is making love or else expecting rain
And the Good Samaritan, he’s dressing, he’s getting ready for the show
He’s going to the carnival tonight on Desolation Row
16. “Forever Young” from ‘Planet Waves’ (1974)
15. “Ain’t Gonna Grieve” from ‘The Bootleg Series, Vol 9: The Witmark Demos: 1962–1964’ (2010)
Another great example of a short and catchy tune with the spiritual influences that makes this among one of my favorite Dylan tracks.
14. “Ye Shall Be Changed” from ‘The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991’ (1991)
This has never been performed live nor has it received a release on a studio album. I have no idea why; it is one of the best composed Dylan tracks. The music is grand and catchy, while the lyrics are easy reflective and meaningful.
You drink bitter water
And you been eating the bread of sorrow
You can’t live for today
When all you’re ever thinking of is tomorrow
13. “It’s Alright, Ma (I’m Only Bleeding)” from ‘Bringing It All Back Home’ (1965)
12. “Bob Dylan’s Dream” from ‘The Freewheelin’ Bob Dylan’ (1963)
With haunted hearts through the heat and cold
We never thought we could ever get old
We thought we could sit forever in fun
But our chances really was a million to one
11. “Mississippi” from ‘The Bootleg Series Vol. 8: Tell Tale Signs: Rare and Unreleased 1989–2006’ (2008)
A powerful love story that has whoever Dylan is writing about looking back on his life. Coupled with his raspy voice (which works for the song) and his simple guitar strumming, the “Mississippi” version on this bootleg album is the version to hear.
Well my ship’s been split to splinters and it’s sinking fast
I’m drownin’ in the poison, got no future, got no past
But my heart is not weary, it’s light and it’s free
I’ve got nothin’ but affection for all those who’ve sailed with me
10. “House Carpenter” from ‘The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991’ (1991)
Remember “Man in the Long Black Coat”? Here is the song it is based off of — the classic tune many folk artists have sung about.
09. “I Don’t Believe You (She Acts Like We Never Have Met)” from ‘Another Side of Bob Dylan’ (1964)
A song about Dylan wondering why a woman left him. The laughs throughout the song give a sense that this is not something he is all too concerned about, but the lyrics may tell a different story.
It’s all new t’ me
Like some mystery
It could even be like a myth
Yet it’s hard t’ think on
That she’s the same one
That last night I was with
From darkness, dreams’re deserted
Am I still dreamin’ yet?
I wish she’d unlock
Her voice once an’ talk
’Stead of acting like we never have met
08. “Maggie’s Farm” from ‘Bringing It All Back Home’ (1965)
A big fuck you to the folk revival movement, where Dylan had made his bread and butter. He wanted to branch out and try new sounds and write different sounds. The song is at the epicenter of one of the most controversial musical shows in history: Dylan going electric.
Looking back, now and as a teen, it is Dylan being punk rock. And I love it.
07. “The Death of Emmett Till” from ‘The Bootleg Series, Vol 9: The Witmark Demos: 1962–1964’ (2010)
One of the songs from English class that helped me see Dylan in a new light.
06. “Let Me Die In My Footsteps” from ‘The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991’ (1991)
I am shocked this was never given a full release. The song is one of Dylan’s strongest poetic songs. Its call for the narrator to be a martyr for the commond good still packs an emotional punch.
If I had rubies and riches and crowns
I’d buy the whole world and change things around
I’d throw all the guns and the tanks in the sea
For they are mistakes of a past history
Let me die in my footsteps
Before I go down under the ground
05. “Don’t Think Twice, It’s All Right” from ‘The Freewheelin’ Bob Dylan’ (1963)
04. “Oxford Town” from ‘The Freewheelin’ Bob Dylan’ (1963)
I wish this song was longer, but its power is in its words and shortness.
Oxford Town around the bend
He come in to the door, he couldn’t get in
All because of the color of his skin
What do you think about that, my frien’?
03. “Hurricane” from ‘Desire’ (1976)
Dylan returned to his protesting days with a song about the imprisonment of Rubin “Hurricane” Carter. Its a song that details the ugly racism of society, and Dylan does not shy away from any subject matter. The song brought on controversy, but shows the powerful medium of music. Carter was released after serving 20 years
Now you don’t wanta have to go back to jail, be a nice fellow
You’ll be doin’ society a favor
That sonofabitch is brave and gettin’ braver
02. “When the Ship Comes In” from ‘The Times They a-Changing’ (1964)
My favorite vocal performance by Dylan, as well as a gorgeous guitar melody.
01. “Shelter from the Storm” from ‘Blood on the Tracks’ (1975)
This song is Dylan’s most powerful song. But it is also the song where I did a 180 on Dylan and his music. In a high school English class, we sat and listened to the song and broke down the lyrics line-by-line. It was an eye-opening experience that first really gave me the notion that music was more than just… well… the music. It can offer stories, messages and something much deeper than I would have liked to admit.
“Shelter from the Storm” threw the gates open for me to the world of music as an artistic endeavor and not just a world to make catchy songs. I still wonder: Who is she?
Suddenly I turned around and she was standin’ there
With silver bracelets on her wrists and flowers in her hair
She walked up to me so gracefully and took my crown of thorns
“Come in,” she said, “I’ll give you shelter from the storm”.