20/80 … A Twenty-Song Playlist to Celebrate Bob Dylan’s 80th Birthday

On Monday, May 24th, Bob Dylan will turn 80 years old. As a way of wishing him well, celebrating his birthday, and thanking him for nearly six decades of unforgettable music, I’ve put together this playlist of twenty songs of his that I never tire of hearing. I hope that you’ll enjoy listening to this post, as well as reading it!

A few preliminary notes about the playlist. First, I’ve listed the songs in chronological order based upon the release date of the album they appeared on, so their placement on the list does not denote any judgment on my part as to their rank in significance. Second, I set an arbitrary limit of 20 songs for the list, for reasons of manageability in terms of the time needed, both for me in creating the post, and for you in reading and (hopefully) listening to it. Third and last, since the selection criteria for the list was both highly personal and arbitrarily limited, some of you may be dismayed to find one or more of your own Dylan favorites missing … in that case, please provide a comment with your suggested addition(s) to the list, and if there are enough to warrant it, I’ll include them all in a follow-up post.

And now, please enjoy 20/80, and Happy Birthday, Bob!

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(1) Blowin’ in the Wind – The opening song on his legendary 1963 album, The Freewheelin’ Bob Dylan, with its iconic cover photo of Bob and his girlfriend at the time, Suze Rotolo, walking arm-in-arm down a wintry Greenwich Village street. The allegorical questions this ballad posed to its listeners were unanswerable then, as they remain today. Yet the questions themselves somehow still matter …

” … how many times must a man look up
Before he can see the sky?
And how many ears must one man have
Before he can hear people cry?
Yes, and how many deaths will it take ’til he knows
That too many people have died?

The answer, my friend, is blowin’ in the wind
The answer is blowin’ in the wind.”

Listen to the album track here.

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(2) Masters of War – Another powerful song from the Freewheelin’ album, with Dylan angrily spitting out his condemnation of those anonymous bureaucrats who plan and plot wars from behind the safety of their comfortable desks …

“You fasten all the triggers
For the others to fire
Then you sit back and watch
When the death count gets higher
You hide in your mansion
While the young people’s blood
Flows out of their bodies
And is buried in the mud.”

Listen to the album track here.

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(3) A Hard Rain’s A-Gonna Fall – Yet again, an unforgettable song from Freewheelin’. And a very prophetic one as well. The “hard rain” Dylan warns about foreshadowed, quite literally, the acid rain crisis of the 1970s and 1980’s. And more figuratively, it describes in chilling images the many and varied environmental disasters looming in the wake of the world’s continuing indecisive responses to climate change …

“And what did you hear, my blue-eyed son?
And what did you hear, my darling young one?
I heard the sound of a thunder that roared out a warnin’
Heard the roar of a wave that could drown the whole world
Heard one hundred drummers whose hands were a-blazin’
Heard ten thousand whisperin’ and nobody listenin’
Heard one person starve, I heard many people laughin’
Heard the song of a poet who died in the gutter
Heard the sound of a clown who cried in the alley
And it’s a hard, and it’s a hard, it’s a hard, it’s a hard
It’s a hard rain’s a-gonna fall.”

Listen to the album track here.

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(4) Bob Dylan’s Dream – In this under-appreciated gem from Freewheelin’, Dylan turns his prophetic vision inward, away from social issues and toward personal matters. In his dream, he returns to the room where he and his childhood friends would gather after school, but does so as an adult, with the tragic awareness of the changes that time will inflict on those youthful friendships that seemed so permanent and unchangeable …

“With hungry hearts through the heat and cold
We never much thought we could get very old
We thought we could sit forever in fun
And our chances really was a million to one

As easy it was to tell black from white
It was all that easy to tell wrong from right
And our choices there was few
So the thought never hit
That the one road we traveled would ever shatter or split

Now many a year has passed and gone
Many a gamble has been lost and won
And many a road taken by many a first friend
And each one I’ve never seen again

I wish, I wish, I wish in vain
That we could sit simply in that room again.”

Listen to the album track here.

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(5) Boots of Spanish Leather – One of Dylan’s most poignant ballads, from his 1964 album The Times They Are A-Changin’. It tells the tale of two young lovers, on opposite sides of the ocean, and heading in opposite directions in their relationship. She, sailing away geographically and emotionally, offers to send a gift for him to remember her by. He, waiting ashore and desperate for her to return, pleads for the one gift she’s unable to give him …

“If I had the stars from the darkest night
And the diamonds from the deepest ocean
I’d forsake them all for your sweet kiss
For that’s all I’m wishin’ to be ownin’

That I might be gone a long time
And it’s only that I’m askin’
Is there something I can send you to remember me by
To make your time more easy passin’

Oh, how can, how can you ask me again
It only brings me sorrow
The same thing I want from you today
I would want again tomorrow.”

Listen to the album track here.

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(6) My Back Pages – One of his most thoughtful early ballads, from the second album he released in 1964, Another Side of Bob Dylan. Here he casts his sharp critical gaze inward, castigating his youthful self for thinking he was so mature in his certainties about life, and belatedly recognizing the maturity of admitting to uncertainty. It features one of the most ironic, and to me most memorable, poetic lines in his work – “I was so much older then, I’m younger than that now” …

“In a soldier’s stance, I aimed my hand at the mongrel dogs who teach
Fearing not that I’d become my enemy in the instant that I preach
My existence led by confusion boats, mutiny from stern to bow
Ah, but I was so much older then, I’m younger than that now

Yes, my guard stood hard when abstract threats too noble to neglect
Deceived me into thinking I had something to protect
Good and bad, I define these terms quite clear, no doubt, somehow
Ah, but I was so much older then, I’m younger than that now.”

Listen to the album track here.

And watch a live performance by the all-star band assembled for Dylan’s 30th anniversary concert here.

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(7) It Ain’t Me Babe – Also from the Another Side album. Once again, a ballad of two lovers with opposite dispositions, but unlike the story Dylan told in “Boots of Spanish Leather”, here the issue isn’t that one of them needs more freedom than the other; in this case, what drives the couple apart is that one of them can’t give the other enough freedom …

“You say you’re lookin’ for someone
Who’s never weak but always strong
To protect you and defend you
Whether you are right or wrong
Someone to open each and every door
But it ain’t me, babe
No, no, no, it ain’t me, babe
It ain’t me you’re lookin’ for, babe.”

Listen to the album track here.

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(8) It’s Alright Ma (I’m Only Bleeding) – From the 1965 album Bringing It All Back Home, considered by some to be Dylan’s most influential album, the one in which he transitioned fully from the acoustic folk sound of his first four albums to the electric rock’n’roll format he had introduced a year before at the Newport Folk Festival. This rapid-fire outpouring of poetic outrage was aimed at targets far and wide, among whom were very likely those folk-purists in the audience at Newport who notoriously responded to his performance with hisses and boos. It features two of his most famous lines – “Even the president of the United States / Sometimes must have to stand naked,” and “He not busy being born is busy dying” …

“I scuff
At pettiness which plays so rough
Walk upside-down inside handcuffs
Kick my legs to crash it off
Say okay, I’ve had enough
What else can you show me

And if my thought-dreams could be seen
They’d probably put my head in a guillotine
But it’s alright, Ma, it’s life, and life only.”

Listen to the album track here.

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(9) Like a Rolling Stone – From the second album Dylan released in 1965, Highway 61 Revisited. Probably his most recognizable song, from the very first notes of the memorable organ introduction improvised by legendary session musician (and soon to be co-founder of the jazz-rock ensemble Blood, Sweat & Tears) Al Kooper. And certainly one of the harshest, most unforgiving judgments Dylan has ever rendered on any of the many characters who populate his songbook …


“You never understood that it ain’t no good
You shouldn’t let other people get your kicks for you
You used to ride on a chrome horse with your diplomat
Who carried on his shoulder a Siamese cat
Ain’t it hard when you discovered that
He really wasn’t where it’s at
After he took from you everything he could steal

How does it feel, how does it feel?”

Listen to the album track here.

And listen to this blistering live version Dylan delivered with The Band from their 1974 Before the Flood concert tour here.

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(10) Ballad of a Thin Man – Another song from Highway 61 – this one a surrealist portrait of a mysterious “everyman” generically named “Mr. Jones”. Dylan’s dream-like images lock us into a vision teeming with confusion, suggestive of the chaotic changes that were beginning to manifest in the latter half of the 1960s. Yet another memorable line that captured the entire decade – “Something is happening here and you don’t know what it is / Do you, Mr. Jones?” …

“You’ve been with the professors and they’ve all liked your looks
With great lawyers you have discussed lepers and crooks
You’ve been through all of F. Scott Fitzgerald’s books
You’re very well-read, it’s well-known
But something is happening here and you don’t know what it is
Do you, Mr. Jones?”

Listen to the album track here.

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(11) Positively Fourth Street – Recorded during the Highway 61 sessions, released first as a single to follow up the “Like a Rolling Stone” single, and then subsequently included as an album track on Dylan’s first greatest hits collection in 1967. This may well be THE harshest, most unforgiving judgment Dylan ever pronounced …

“You’ve got a lotta nerve to say you are my friend
When I was down you just stood there grinnin’
You’ve got a lotta nerve to say you got a helping hand to lend
You just want to be on the side that’s winnin’

You see me on the street, you always act surprised
You say “how are you?”, “good luck”, but ya don’t mean it
When you know as well as me, you’d rather see me paralyzed
Why don’t you just come out once and scream it.”

Listen to the album track here.

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(12) Most Likely You Go Your Way (And I’ll Go Mine) – From the 1966 double-album Blonde on Blonde. In this song, Dylan continues his long-time exploration of all the ways that lovers can drift apart. Bitterness and disappointment are the predominant emotions, with just the slightest undertone of hopefulness …

“Sometimes, it gets so hard to care
It can’t be this way everywhere
And I’m gonna let you pass
Yes, and I’ll go last

Then time will tell
Who has fell
And who’s been left behind
When you go your way and I go mine.”

Listen to the album track here.

And listen to this impassioned live version from Dylan and the Band, with which they opened the Before the Flood concert that I was fortunate to attend at Madison Square Garden in 1974, here.

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(13) Stuck Inside of Mobile with the Memphis Blues Again – Also from Blonde on Blonde. Easily one of the most uninterpretable of Dylan’s many difficult-to-decipher songs, but long one of my favorites for the way its imagery and its melody both get stuck inside my head for hours after hearing it. I don’t expect to ever figure out what any of it means, but the verses quoted below have always struck me as being a pretty good indicator of what Dylan must have been feeling about life at the time …

“Now, the rainman gave me two cures
Then he said, “Jump right in”
The one was Texas medicine
The other was just railroad gin
And like a fool I mixed them
And it strangled up my mind
And now people just get uglier
And I have no sense of time

And here I sit so patiently
Waiting to find out what price
You have to pay to get out of
Going through all these things twice.”

Listen to the album track here.

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(14) All Along the Watchtower – From the 1967 album John Wesley Harding, the album which signaled Dylan’s third career transition, away from the rock-flavored sound of his past three albums and toward a quieter folk-rock country-tinged sound. Every track on this album demonstrated Dylan’s move away from the inscrutable – often incomprehensible – lyrics of his earlier albums, and towards a more symbolic but more readily understandable form of poetic versifying. No track demonstrated this evolution in Dylan’s artistry more powerfully than the ominous imagery bursting forth here …

“All along the watchtower
Princes kept the view
While all the women came and went
Barefoot servants, too
Outside in the cold distance
A wildcat did growl
Two riders were approaching
The wind began to howl.”

Listen to the album track here.

And listen to Jimi Hendrix’s amazing re-interpretation here.

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(15) Girl from the North Country – Originally released in acoustic solo format on the Freewheelin’ album, Dylan brought back this ode of remembrance of a long-ago love for his 1969 country album Nashville Skyline, and made the brilliant choice to record it as a duet with Johnny Cash. This powerful electric version has always been the one I prefer – the contrasting emotionally-charged vocals of Dylan and Cash as they trade verses deepen the profound nostalgia of the lyrics to an almost palpable level …

“If you’re travelin’ to the north country fair
Where the winds hit heavy on the borderline
Remember me to one who lives there
For she once was a true love of mine

See for me that her hair’s hanging down,
It curls and falls all down her breast
See for me that her hair’s hanging down,
That’s the way I remember her best.”

Listen to the album track here.

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(16) Forever Young – From the 1974 album “Planet Waves”, Dylan’s studio collaboration with The Band that preceded their incredible joint Before the Flood concert tour of that same year. It features two versions of this hopeful blessing upon children everywhere – a “fast version” and a “slow version.” The popular network television program “Parenthood”, which aired from 2010 through 2015, opted to use the fast one for its opening theme, but my preference has always been for the slow one. To my ears, these wishes need to be delivered slowly and deliberately; rushing through them seems to rob them of their meaning …

“May your hands always be busy,
May your feet always be swift,
May you have a strong foundation
When the winds of changes shift.
May your heart always be joyful,
May your song always be sung,
And may you stay forever young.”

Listen to the album track here.

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(17) Tangled Up in Blue – From another masterpiece of an album, Blood on the Tracks, released in 1975. Dylan’s earlier albums had occasionally included a song that was the musical equivalent of reading a short story – for instance, “The Ballad of Hollis Brown” on The Times They Are A-Changin’ album. But here we have a song that, when we listen to it, feels more like watching a feature-length movie. Two lovers meet, separate, meet again years later, move in together, fall apart, separate again, and even as the song ends with them back on their own, we know for sure that their story has not yet ended …

“She was married when we first met
Soon to be divorced
I helped her out of a jam, I guess
But I used a little too much force
We drove that car as far as we could
Abandoned it out west

Split up on a dark, sad night
Both agreeing it was best
She turned around to look at me
As I was walking away
I heard her say over my shoulder
‘We’ll meet again someday on the avenue

Tangled up in blue.”

Listen to the album track here.

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(18) Simple Twist of Fate – A somber reflection on the randomness of a chance encounter, and the loneliness left in its wake, from Blood on the Tracks. Another ballad with such vivid imagery, you can practically see every verse being enacted before your eyes …

“They walked alone by the old canal.
A little confused, I remember well,
And stopped into a strange hotel with a neon burning bright.
He felt the heat of the night hit him like a freight train
Moving with a simple twist of fate.

A saxophone someplace far off played
As she was walking on by the arcade
As the light bust through a beat up shade
Where he was waking up.
She dropped a coin into the cup of a blind man at the gate
And forgot about a simple twist of fate.

He woke up; the room was bare.
He didn’t see her anywhere.
He told himself he didn’t care; pushed the window open wide;
Felt an emptiness inside to which he just could not relate
Brought on by a simple twist of fate.”

Listen to the album track here.

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(19) You’re a Big Girl Now – The end of a long love affair, again from Blood on the Tracks. The angry young Dylan is long gone in this heartbreaking song; the singer emotes so much sadness, longing, and regret that we all but feel his loss as our own …

“Bird on the horizon, sittin’ on a fence
He’s singin’ his song for me at his own expense
And I’m just like that bird, oh
Singin’ just for you
I hope that you can hear
Hear me singin’ through these tears

Time is a jet plane, it moves too fast
Oh, but what a shame that all we’ve shared can’t last
I can change, I swear, oh
See what you can do
I can make it through
You can make it, too.”

Listen to the album track here.

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(20) Sara – From the 1976 album “Desire” – an autobiographical cry of pain following the break-up of his marriage to Sara Dylan. Never a very popular entry in Dylan’s catalog – the anguish it expresses is simply too raw. But one not to be ignored, considering its brutally honest rendering of the emotions Dylan was experiencing at the time …

“Sara, Sara
Whatever made you want to change your mind?
Sara, Sara
So easy to look at, so hard to define.

Sara, Sara
It’s all so clear, I could never forget
Sara, Sara
Lovin’ you is the one thing I’ll never regret.”

Listen to the album track here.

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And now for the “bonus track”! Let’s end where we began, with “Blowin’ in the Wind”, performed as a duet with Dylan and Joan Baez during the 1976 Rolling Thunder tour. Watch it here.

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