The most enigmatic musician of the modern era, and now a Nobel laureate to boot. In some ways, it’s tough to write about Dylan’s genius. Some aspects are so obvious that it feels pointless to belabor the point with further words. Other parts are so ephemeral that language struggles to meet the task of description. Talking about his art, that is to say, feels all too much like ‘dancing about architecture.’
But we persist nonetheless. Because the other thing about Dylan’s work is its deep emotional resonances. His music invites us to reflect on our own beliefs and our own deepest feelings. To encounter the strangeness of life, in all its particularity and its universality. To make our inner reflections on selfhood into a shared communal experience. To bridge the horizons between what we know and what we feel to be true.
In writing this list, I set out on that path myself. I’ll be the first to admit that this is a personal list, with at least a couple idiosyncratic choices. I haven’t listened to all his catalog (by any stretch), and I have my own proclivities about when Dylan was truly at his best. So with that in mind, I’m even more interested than usual in hearing from my readers about your favorites. Particularly the more obscure ones. The bootleg recording from 1973, when he tuned his guitar to a Modal D and breathed new life into an old b-side…tell me what you’ve got!
10. Blowin’ in the Wind (The Freewheelin’ Bob Dylan)
Dylan arrived on a folk scene interested mostly in singing the old standards, and on unearthing the lost gems of a previous era. He played that game for a little while himself, but quickly stepped forward. And in doing so, he changed the world. Blowin’ in the Wind is a protest song, but it’s so very much more. The questions aren’t simply rhetorical devices, meant to shame and inspire action; they’re ruminations on the stark limits of human experience, on the blind paths we all walk down, the infinite possibility of the open sky.
In the end, he wrote a song that was both perfectly of its time, and also entirely outside of time. It’s a song we might well still be singing a thousand years from now. A little closer to the answers, hopefully, but still all too aware that the wind sometimes whispers words in a code that humanity may never fully unlock.
9. Subterranean Homesick Blues (Bringing It All Back Home)
Not satisfied with one earth-shaking contribution to the American musical landscape, Dylan released Bringing it All Back Home a scant two years after Blowin’ in the Wind had hit the scene. In his first incarnation, he was the savior of folk music, the symbol of the new depths that could be explored by a boy and his guitar. But now, Dylan turned his attention to rock music—only a decade old, and already in steep decline. It needed a swift kick, and a reminder that rock was meant to snarl, to dislocate, to burn away all that tied us down.
And so he took aim at all of his own idols, and the idols of all his fans. You can almost read it as a form of self-sabotage. They’re going to hate the electric turn, anyways, he muses to himself, so why not let them have it with both barrels? The result is an avalanche of words, which gains momentum with every second – as that underlying chord progression refuses to let up, as Dylan snarls out the litany of abuses inflicted by the simple act of trying to stay alive in a world that cares not one whit for your success or your failure. And as with many of Dylan’s best works, the words sometimes get beyond his capacity to corral them. In a song that shares a great deal of DNA with the proto hip-hop that would come a decade later, the one thing Dylan absolutely can’t do is maintain an even flow. He rushes and waits, just trying to keep from being consumed by the avalanche that he set free.
And good god, the brutal efficiency of “20 years of schooling and they put you on the day shift.”
8. Stuck Inside Of Mobile With The Memphis Blues Again (Blonde on Blonde)
The imagery is brilliant, but more than any other song on this list, I think this track is primarily defined by the backing band. The organ weaving through and around Dylan’s lyrics, sometimes as a counterpoint, sometimes as an emphasis. And the percussion is superb. The ratatat holds the entire enterprise together, preventing the madness of the words from becoming overwhelming. In a less deft performance, this song would quickly become a parody of itself. But somehow, for all seven minutes of its length, they keep everything in balance.
And, in a certain sense, whatever meaning I can glean from the song comes from precisely that point. The truest words of the song are spoken right at the beginning, when the narrator admits: “deep inside my heart, I know I can’t escape.”
7. Most of the Time (Oh Mercy)
I wrote a long post about this song back in the early days of the blog (over 10 years ago, if you can believe it), with a particular focus on its use in High Fidelity. I’ll just quote a little bit of it here…
Bob Dylan’s voice (a handicap at times in his career) is perfectly suited to this situation. Gravelly, wise, but also tender, he tells of the regrets we feel about those we have left behind. The song is about beginning anew, leaving behind the person that you loved. But, there is a delightful tension in lines like:
Most of the time, she ain’t even in my mind
I wouldn’t know her if I saw her, she’s that far behind
Most of the time, I can’t even be sure
If she was ever with me or if I was ever with her
Most of the time, we are fine. But, only most of the time. Sometimes, it hurts so bad you can’t stand it. And I think the singer is in one of those moments. In his constant repetitions that “most of the time” he is okay (doesn’t even miss her, doesn’t even notice that she’s gone), I see as him struggling for something to hold onto. Most of the time, I can survive, but at times like these, it feels very hard. It is not a hopeless song, because he does know that the pain eases and life moves on. But it is a song about how hard it is to lose love, and the struggle that goes on inside.
6. Mr. Tambourine Man (Bringing It All Back Home)
If you want to make the case for Dylan’s Nobel Prize, this song has to feature prominently. The last verse, in particular, is arguably the most beautiful imagery ever put to melody:
Yes, to dance beneath the diamond sky with one hand waving free
Silhouetted by the sea, circled by the circus sands
With all memory and fate driven deep beneath the waves
Let me forget about today until tomorrow
There are a vanishingly small few songs ever written that feel as if they come from beyond this world. This is one such song. It speaks to truths that exceed our own limited understanding. And you can’t help but think that there must be so much more out there somewhere, if only we could hear it. We were lucky enough to be gifted one genius who briefly tapped into the right wavelength and managed to catch four verses. But somewhere out there, all truths are sung, and all worlds are made possible.
5. Mississippi (Love and Theft)
It’s an old man’s song, but not in the straightforward way it’s sometimes understood, as a personal reflection from Dylan on his own age and mortality. It may well be that, but far more importantly it’s a song about what it means for each of us to inhabit our own futures, to flee from that which we once were.
We look forward, resolutely, with all attention on the time still to come. And yet, with each passing day, it becomes harder to avoid glancing back. And when we do, we see that the past never left us. It remains there, patiently waiting, unmastered. We can flee our mistakes, and attack those who force us to remember. But in the end, the evils of our past cannot be escaped. We signed the Declaration of Independence. We fought a Civil War. We envisioned a reconstructed south, one of equality and justice. And then we watched it all crumble and drift away. And all of that is still with us, as much as we’d like to forget it.
So, in the end, recognizing that it’s totally inadequate, we look for solace in a single human connection. And we say: “I know you’re sorry, I’m sorry, too.”
4. Desolation Row (Highway 61 Revisited)
Cinderella, who seems so easy. Ophelia, burned out by 22. Einstein, disguised as Robin Hood, hiding from his past as an electric violin player. The agents and the superhuman crew. They’re all packed together, feeding off one another, growing closer and more fevered in the process.
Each character represents a certain kind of hope, a certain dream. For some it’s escape. For some, it’s simply about finding a way to make meaning out of the chaos. And there’s a certain hopefulness implied in the process, one that’s supplemented by the melody—probably the prettiest Dylan ever composed. But the more time you spend with the song, and try to find the meaning in the words, the more you find yourself trapped by its shifting mirrors. And you begin to understand how so many people could have let themselves into Desolation Row in the first place.
In many respects, this is peak Dylan. A story that invites you in with open arms, and yet which remains utterly inscrutable. It asks you to interpret, even while it challenges the very idea of interpretation. This is Dylan as the anti-Virgil, the perfect guide through the divine comedy of modernity.
3. Like a Rolling Stone (Highway 61 Revisited)
With this song, Dylan showed the world what rock music was truly capable of. It doesn’t bury the 3 minute pop song, but instead elevates it, shows that there’s so much more potential buried in those simple structures. From the first drum kick to the final harmonica solo, this song bulldozes through every limit previously imposed on the genre. How does it feel? It feels great.
2. Just Like a Woman (The Concert for Bangladesh)
The studio version is a good song, no doubt, but probably not even among the five best tracks from Blonde on Blonde. But if you haven’t heard the version from the Concert for Bangladesh, I urge you in the strongest possible terms to check it out. For an artist so totally defined by the endless proliferation of outtakes, alternate versions—and whose vocal efforts varied so widely over the years—I genuinely think that concert represents his peak performative capacity. He played five songs: A Hard Rain’s A-Gonna Fall, Blowin’ in the Wind, It Takes a Lot to Laugh, It Takes a Train to Cry, Love Minus Zero/No Limit, and Just Like a Woman. And they’re all perfect. But none more so than this one.
The basic sadness of the song has always been in tension with its deep cruelty, and has driven so many to read it as pure misogyny. And in other versions, that feels completely fair. But on this night, we were gifted with something else. A version of the song that doesn’t erase those meanings, but reveals something far deeper within them. Because, in his voice, on this night, the cruelty is reflected backward as well as forward. It’s a song about what we do to each other. About the intolerable pain that we inflict, unrealizing and unwanting, upon those that we love. About the lengths to which we drive them. About the expectations we impose, and the debts we underwrite, while trying to hold something together.
The song begins “nobody feels any pain” – and only through this version of the song does the hollowness of that claim finally become clear. Because of course there is pain, and of course he feels it too. He watches, he sees her trying to brush it aside, and he recognizes the falseness of that mask. But only because he himself understands all too well what it would mean to let the pain overtake us. After all, later in the bridge he says “But what’s worse, is this pain in here, I can’t stay in here.”
And suddenly all the cruelest lines take on new meaning. Yes, she is shallow and boring and immature. But no more so than him. Together they weaved a story, and together they tried to make it real. But just as most love stories do, this one cracked apart, and they were rent and torn in the process.
So now he offers a lamentation. That their time together brought so much pain, that he himself is the cause for so much of it, and that this very fact makes it impossible for him to offer any solace. She has broken, he has done it, and he bows heavily under the weight of that responsibility. Because, every way he turns, there’s pain.
I know that this isn’t the only possible interpretation of the song, and I don’t discount the more straightforward take that it’s simply a brushoff, directed at a woman in pain, wielded by a man who understands precisely how to use dismiss that pain as valid. But, the way he sings that song on that night, I simply can’t accept that meaning. This version of the song springs from a well of deep sympathy. If it is cruel, it’s cruel in the sort of way that we are all cruel—in the terror that comes from realizing that every time we open our hearts we don’t just risk losing something of ourselves, we also risk taking something from someone else.
1. Tangled Up in Blue (Blood on the Tracks)
The perfect Dylan song. The lyrics are brilliant: endlessly evocative without losing the sense of cryptic meaning. A set of interlocking stories, not connected in any obvious sense, but bound together by a shared sense of recurrence. This has all happened before and will all happen again. And yet, the eternal return is not simply a matter of repetition. The stories change, the characters shift, context blurs, and meanings shift. Time can’t be escaped, nor understood. It circles around us, forming memories and then taking them away.
The result is a song told in a series of moments, flashes of possibility. Each scene carries its own internal structure and coherence. And in each case, the narrator achieves some sort of epiphany. A flash of recognition (“I just kept looking at the side of her face, in the spotlight so clear”), of transition (“Lord knows I’ve paid some dues, getting through”), of memory (“I seen a lot of women, but she never escaped my mind”), of passion (“And every one of them words rang true and glowed like burning coal”), of limitation (“the only thing I knew how to do was keep on keeping on”).
Is it the same man, encountering different women? Or vice versa? Or are these the same two souls meeting again and again, but unable to remember? Or are these simply random encounters with no connection at all, other than the simple reality that every encounter carries hints of all the others. And in the end, there’s nothing to be done except take another step down the road, see what waits beyond the next rainbow’s end.
11. Shelter From the Storm (alternate version from the Jerry Maguire soundtrack)
12. Sad Eyed Lady of the Lowlands (Blonde on Blonde)
13. Love Minus Zero/No Limit (Bringing It All Back Home)
14. I Want You (Blonde on Blonde)
15. Not Dark Yet (Time Out of Mind)