The thing that struck me about Bobby was his despair, that deathlike quality about him… People live with hope for green trees and beautiful flowers… but Dylan seems to lack that sort of simple hope.

– Suze Rotolo, in No Direction Home: The Life and Music of Bob Dylan (1986)

Ain’t talkin’, just walkin’
Up the road around the bend
Heart burnin’, still yearnin’
In the last outback, at the world’s end

– Bob Dylan, “Ain’t Talkin’” (2006)

[Note: I started working on this back in March and then quit after about a month. I’m still not quite half done with the full 120-song list of annotations, but it’ll get done eventually. For now, here’s an intro and part 1/7…]

Folks, I love me some lowbrow entertainment. In difficult times such as these, I tend to forego the “high art” and seek solace more in what you might call blobbin’ out – binge-watching sitcoms or superhero flicks while scrolling through social media and shoveling various combinations of salt, fat, and carbs down my gullet. Let’s call that the path of least resistance. I assume we all know it well, not least in this age of COVID-19.

But there have been times in my life when I felt similarly overcome by the weight of the world and yet found consolation in slightly more meaningful forms of art or entertainment, let’s say reading Dostoyevsky or singing in a choir. Looking back, those have been the sources of succor and inspiration that have really stuck with me, that have sustained and even slowly shaped me for the better over my twenties and thirties, like the persistent drip of water over rock.

One such period in my life was the fall of 2016, when in my gloomy state I became utterly obsessed with Bob Dylan, that endlessly polarizing and iconic weirdo who perhaps has always bestridden the borderland between “high” and “low” art, not that it much matters. That fall was a time when I felt like I was getting pummeled from various sources—the strain of our nation’s politics, a rough patch in my private life, and most bruisingly, the daily struggle and massive personal inadequacies I faced as a second-year Middle School English teacher.

For months, I felt like I was trudging through dark space, my soul tethered to a lead balloon. Perhaps the word “desolation” best captures the range of emotions I bore within – some mix of loneliness, anxiety, melancholy, and despair. And yet, fall of 2016 also happened to encompass that bizarre episode when the Swedes awarded Bob Dylan a Nobel Prize in Literature and set off a brief firestorm of cultural debate, a happenstance that would not be wasted on me.

Yes, of course I’d listened to a little Dylan before – songs like “Blowin’ in the Wind”, “The Times They Are A-Changin’” and “Knockin’ on Heaven’s Door”, exhaustively overplayed anthems I’d learned to strum on my guitar more than a decade prior. But when Bob won his Nobel, the ensuing cultural brouhaha piqued my curiosity and made me wonder what all the fuss was about, and what perhaps I’d been missing. I started listening again… and didn’t stop.

I fell hard down that rabbit hole. As the months passed, I made mixtape after mixtape, searching deeper and deeper into his now-60-year catalogue and running up my iTunes bill in the process. By the end, I had close to 400 Dylan songs on my computer and a musical fixation that had become reliable joke fodder for my closest friends. All told, I listened to nothing but Bob Dylan for seven months straight, until – as it happens – the fog of my desolation began to lift.

Was it Bob’s music that cured me, that chased the doldrums away? No. Correlation is no causation. But I have no doubt that it did help me endure those dreary days, as did therapy, friends and family, and any number of other unaccounted for graces. Yet what I learned from the deep-dive into Dylan’s works was a paradox in my relationship to art: I was oddly fortified and buoyed amid my own despair by this raging misanthropic weirdo’s generally pessimistic and often disturbing music. In fact, Dylan’s incurable melancholy – sometimes heroic, sometimes stoic, often bitter – seemed to help prop me up as I waited out my own season of despair.

It turns out I didn’t need blithe, cheer-me-up songs. I needed songs that mirrored what I was feeling – alienation, frustrated longing, a sense of impending doom, etc. – and Dylan’s catalogue offered plenty of it. He has often played a bard of the apocalypse; stark warnings and bizarre portentous visions have been as much his calling card as that of John the Revelator or the Old Testament Prophets. But he’s also never ceased to plumb the depths of his own emotional, spiritual, and romantic turbulence for material, even if generally shying away from overtly autobiographical lyrics. Throughout his career, Bob has swung wildly in life and music from one muse or source of inspiration – and eventual disillusionment – to another. Nothing has ever seemed to quite satisfy his “forgetful heart”, except perhaps the music itself, his great vehicle of expression. And joining Bob on this strange journey gave me a little courage of my own.

For whatever reasons, the 120 songs that make up the following list are those that meant the most to me during that tough seven month stretch – and mean the most to me to this day. Thus, they are the ones I most wanted to reflect upon and share with you during this dark and strange time that we now face together. Before I begin, let me offer just a few disclaimers:

• First, just about everything that can be said about Dylan has been said. I have no good excuse to add to the massive record of books, articles, blogposts, academic papers, etc. that have been written about his life, work, and influence on American culture. I will only say that I “discovered” this all for myself and experienced it in my own way, in my own time, and that is what has made it fresh and meaningful. In other words, this list is as much about me as it is about Bob, and perhaps that’s what makes it unique.

• Which brings me to my second disclaimer: as a very personal list, this heavily reflects my own aesthetic, political, and philosophical biases. It is in no way intended to be “definitive”. If you’re looking for an annotated Dylan highlights list made by actual experts and critics, try Rolling Stone magazine’s “100 Greatest Bob Dylan Songs” from May, 2016. It’s full of great commentary, but only 60 of my 120 make their top 100, and I’m fine with that. I fully admit to having omitted a number of Dylan “classics” that just don’t mean much to me or that I outright dislike – songs like “Chimes of Freedom”, “Subterranean Homesick Blues”, “It’s All Over Now, Baby Blue”, “Ballad of a Thin Man”, “Rainy Day Women #12 & 35”, “Lay, Lady, Lay”, “Gotta Serve Somebody”, “Jokerman”, etc. Sorry if I skipped your favorites!

• Third disclaimer: in the same way that this list isn’t intended to be “definitive”, neither are my interpretations of the songs. There are a lot of rabid Dylan fans out there – so-called “Dylanologists” – and as much as I love their passion, I generally find them insufferably condescending and annoying. He has an entire subset of devotees who take delight in correcting the rest of us, which I suppose is what you find in every field of “expertise”, no matter how trivial. Isn’t it human nature to just enjoy lording it over others? Anyway, sometimes in art, the most important interpretations are the ones that mean the most to an individual, not the “correct” ones. I have tried to reflect a little on both in my comments. But let’s remember, Dylan is famous for lyrics that are often deliberately opaque and surreal. You’re forgiven for not always “getting” Dylan. No one fully does.

• Fourth disclaimer: at 120 songs, this list is incredibly self-indulgent. I originally set out to whittle my playlist down to 50 and then to 100 songs and I just couldn’t do it. I was spinning in my tracks for days trying to choose which to include and which to leave out. I finally threw my hands in the air and settled on 120, as if 100 wasn’t already enough. I also couldn’t begin to put them in order according to preference, so I have instead simply arranged them in chronological order according to when the songs were first written and recorded – a chronology based on the research of Clinton Heylin, who is quoted ad nauseam throughout.

• Finally, I should note: I have little doubt that on a personal level Bob Dylan has been an extraordinarily hard man to live with. I can’t imagine trying to love someone through all of those toxic moods and bizarre phases, not to mention the decades of intense touring, the substance abuse, infidelity, and general hard livin’. I don’t need to know what kind of father, husband, or friend he’s been, or even what he really stands for. Bob’s never been the sort of icon you’d want to idolize – he’s often made it easy not to – and that’s for the best, because it puts the focus on the music, which, with all due respect to Bob, is bigger than him anyway. At the same time, I’d be lying if I said I haven’t in some sense loved the man through his music, not least because he has always poured so much of his messy, ugly humanness into making it, for better and for worse.

Ultimately, if there’s anything good I can say about having to self-isolate for months on end, it’s that I’ve finally had both the time and cause to work on this ridiculous 120-song annotated Dylan playlist that I’ve wanted to compile for three years. Desperate times call for desperate measures, and if nothing else this project has given me something to do. It’s been fun, and weird. But I hope in any case that it’ll serve as a worthwhile diversion for at least one fellow traveler out there, stuck at home, whether Dylanologist or Dylan newbie. Enjoy.

I. 1961-1963

(21 Songs)

Bob Dylan first showed up in New York City in January 1961 at the tender age of 19 after dropping out of the University of Minnesota. In three years, he would rise from a scruffy no-name Jewish kid out of a small town in the Midwest to the “spokesman of a generation,” performing in front of mass audiences at the March on Washington, Newport Folk Festival, and Carnegie Hall, and even walking off the set of the The Ed Sullivan Show.

He began his career modeling himself after a long line of hitch-hiking guitar-slingers – most notably his hero Woody Guthrie – and imitating folk, blues, and gospel standards, a number of which featured on his raw first album, Bob Dylan (1962), which sold only a few thousand copies in the U.S. Yet Dylan quickly shifted to writing more of his own material, churning out dozens of new songs in both 1962 and 1963 while still relying heavily on guidance and inspiration from the folk and blues traditions, from which he adapted numerous tunes, story-telling devices, and lyrical elements. A host of beautiful early Dylan songs dealt inventively with classic folk and blues themes of individual hardship, dislocation, and lost love, some of which – songs like “Don’t Think Twice, It’s Alright” and “Girl from the North Country” – would later be regarded as among his best compositions.

At the same time, many of Dylan’s works from 1962-3 also took thematic inspiration from the tense politics of the day, charging headlong at weighty topics like racial injustice, rural poverty, militarism, corruption, the threat of nuclear annihilation, and the evils of war. For a while, as Heylin notes, Dylan was “keeping his lyric notebook next to a copy of the morning newspaper.” Songs like “Blowin’ in the Wind,” “Masters of War,” and “A Hard Rain’s a-Gonna Fall” set the tone for his second album, The Freewheelin’ Bob Dylan (1963), which became a smash hit, eventually going platinum. It was these politically-charged songs – variously called “topical,” “message,” “finger-pointing,” or “protest” songs – that most captivated fans among the then-intertwined Folk Revival and Civil Rights movements and helped propel the young Dylan to fame. His third album, The Times They Are A-Changin’ (1964), offered them only more of what they craved, replete with “social preening and black-and-white moralism.” As blogger Jeff Meshel puts it, “Bobbie had figured out that the coolest chicks were at the demonstrations. All the Joan Baezs of the world found indignant rage a serious turn-on, and Bob was right there, poison pen in hand.”

And yet, by the fall of 1963, the appeal of his role as folk icon and political “spokesman of a generation” was already wearing thin for the 22 year-old, who began to quietly rebel against the topical and musical expectations imposed on him by his fans. As Heylin explains, by the time of JFK’s assassination that November, “the first phase of his career had drawn to a close. When he emerged again in the new year, he had put away all protest things.”

1.) “Song to Woody” (1961)

The very last thing that I’d want to do
Is to say I’ve been hittin’ some hard travelin’ too

Dylan penned this heartfelt tribute to his hero Woody Guthrie after visiting him in January at a New Jersey psychiatric hospital where the folk icon was slowly wasting away from Huntington’s disease. Likely the first song Dylan wrote upon coming to New York, it “exudes a persuasive if naïve charm borne of reverent respect” and is appropriately set to the tune of one of Guthrie’s own songs, “1913 Massacre,” while also invoking several of Bob’s other heroes – Cisco Houston, Sonny Terry, and Lead Belly. As one of two “original” compositions on his self-titled first album, the song functions as a kind of artistic statement of purpose from the idealistic youngster, illustrating his self-conscious embrace of the folk tradition and romantic yearning for the life of the hard travelin’ troubadour, presaging his own eventual “Never Ending Tour.” Here we glimpse an earnest young man reaching for something greater in himself, a pure vision of the kind of person and artist young Bob hoped to become.

2.) “Talkin’ New York” (1961)

Walk around with nowhere to go
Somebody could freeze right to the bone
I froze right to the bone

This jaunty tune is one of a number Dylan wrote in 1961-2 in the traditional spoken-word style of “Talkin’ Blues,” a term coined by southern blues musician Chris Bouchillon in the 1920s. Mixing satire and self-deprecating humor, Dylan gives us a semi-autobiographical account of the ups and (mostly) downs of his dreary first few months in the Big Apple, including his struggles to find gigs and make it as a musician. He convincingly captures that sense of urban isolation that chills a person “right to the bone” and tends to afflict newcomers to a city – not knowing how to connect, feeling disoriented and adrift, struggling to make ends meet. As Heylin explains, the informal “Talkin’ Blues” style served Dylan well: “Its half-sung, half-spoken manner of delivery released the performing poet in him.” Thus, in this song we get an early taste of Dylan’s lyrical wit, with lines like, “A lot of people don’t have much food on their table / But they got a lot of forks and knives / And they gotta cut something…”

3.) “Talkin’ Bear Mountain Picnic Massacre Blues” (1961)

There’s a bran’ new gimmick every day
Just t’ take somebody’s money away

My favorite of Dylan’s “Talkin’ Blues” tracks, this fantastic little piece of absurdist satire was one of the Greenwich Village crowd-pleasers that helped get Dylan noticed in mid-1961 and signed to Columbia, although it was not included on his first record. Here we see Bob beginning to pull song material from the pages of the news while also not letting the facts “get in the way of a good story.” According to Heylin, the narrative “[t]aken from a story in the New York Herald Tribune… tells of a chartered boat trip to Bear Mountain that had been abandoned because thousands of counterfeit tickets had been sold to unwitting customers.” In Dylan’s highly embellished retelling, all manner of calamity befalls his everyman narrator—the ship sinks, he loses track of his wife and kids, get chased by cops, bruised and bloodied, knocked out and stripped naked, barely making it out of the “massacre” alive before swearing off picnics forever. The song hilariously captures the disorienting, humiliating feeling you get from being sold a bill of goods by some slick salesman or screwed over by a corporation. It would make a great theme song for the Consumer Protection Bureau. Full disclosure: I have a pipedream of turning this into a children’s book someday.

4.) “I Was Young When I Left Home” (1961)

Not a shirt on my back
Not a penny on my name
Well I can’t go home this a’way

Though unreleased until 2005 and a relatively minor Dylan song, there is perhaps no other in his canon that can tug at my heartstrings quite like this one. The lyrics and tune draw heavily from the traditional song “900 Miles” and Hedy West’s “500 Miles,” both songs of lament told from the point of view of someone adrift in the world and far from home. It was the last song Dylan wrote in 1961 and betrayed a deep “homesickness that still gnawed at him” as he prepared for a visit home to Minnesota that December. The wrenching lyrics and pathos of his voice capture the sadness, shame, and nostalgia that come from having been too long away from home and distant from the people who love you most, sensing your roots slip away. Despite the narrator’s apparent regret at having made his “home out in the wind,” it’s a line that will define much of Dylan’s own life and which reveals, as Heylin notes, “everything that drove him to New York in the first place” – which somehow only makes it sadder. For Dylan, there was no going back. A great version was done by Antony + Bryce Dessner for the 2009 Dark Was the Night compilation. It takes something pretty powerful to jerk a tear loose in my tear ducts, but this song can do it.

5.) “Ballad for a Friend” (1962)

Years ago we’d hang around
Watchin’ trains roll through the town
Now that train is a-graveyard bound

This tender ballad, again unreleased until decades later, is another raw little-known song Dylan wrote amid that bout of nostalgia and homesickness brought on by his Christmas trip home to Minnesota. Although 1962 would be a year of astonishing success for Dylan as he penned almost 50 new songs – including a number of folk classics that would vault him to notoriety – it began on a rather subdued note with this wistful, mournful tune. The ballad recounts reminisces of joyful times Dylan (or the narrator) spent with a close childhood friend in that North Country “[w]atchin’ trains roll through town” or hanging out among the “[l]akes and streams and mines so free,” before revealing the tragic conclusion that “his former friend has been found dead on a Utah road.” It was likely inspired by news Dylan received shortly after leaving home that his lifelong friend Larry Kegan had been left permanently disabled from an accident. Like “I Was Young When I Left Home,” it is haunting and evocative because it touches on that sense we sometimes have of something being irretrievably lost from childhood, in this case, a best friend.

6.) “Let Me Die in My Footsteps” (1962)

And some people thinkin’ that the end is close by
‘Stead of learnin’ to live they are learning to die
Let me die in my footsteps
Before I go down under the ground

How relevant is this song to our current predicament? As hundreds of millions of people around the world now huddle indoors to slow the spread of coronavirus, this joyous rebuke to the nuclear hysteria of the 1950s and 60s has repeatedly bubbled to the surface of my mind. Of course, staying home amid a pandemic is different from the paranoiac “duck-and-cover” drills and fallout shelter craze Dylan’s generation endured – and which this song addresses – but the question of how much power we give to fear remains ever relevant. In 1962, fears of nuclear war were not entirely unfounded – the Cuban Missile Crisis came later that year – and yet here Bob offers us a simple and heartening affirmation of life lived in death’s shadow, bringing to mind the Biblical admonition not to “fear those who kill the body but cannot kill the soul.” Although it was a precursor to “A Hard Rain’s a-Gonna Fall,” which actually replaced it on The Freewheelin’ Bob Dylan, this song is one of Bob’s standout early tracks, the best version of it being released in 1991 on The Bootleg Series Volumes 1-3.

7.) “Blowin’ in the Wind” (1962)

Yes, ’n’ how many times can a man turn his head
Pretending he just doesn’t see?

In many ways, “Blowin’ in the Wind” was the song that “announced” Dylan to the world, propelling him to folk stardom when Peter, Paul, and Mary’s cover topped the charts in 1963. And yet it’s hard to say exactly what the 21-year-old intended when he penned the iconic folk singalong, played at countless rallies and summer camps from it seems like time immemorial. As Peter Yarrow said, “like a true poet, I think [Dylan] stepped back from prescribing an interpretation.” Bob’s reflections in 1962 offer little clarity: “[T]he answer is blowing in the wind. It ain’t in no book or movie or T.V. show or discussion group. Man, it’s in the wind… Too many of these hip people are telling me where the answer is but oh I won’t believe that. I still say it’s in the wind and just like a restless piece of paper it’s got to come down some time… But the only trouble is that no one picks up the answer when it comes down…”

Perhaps the song is a rumination on the zeitgeist or winds of change swirling around him amid the protest movements of the early 1960s. Perhaps, as Pope John Paul II asserted after Dylan’s 1997 performance of it in Bologna, it’s a metaphor for the Ruach Elohim or Holy Spirit leading people toward God or justice or ultimate truth. Or perhaps the tension of not quite knowing what is blowing in the wind is in fact the point and part of what makes the song special – as a meditation on all that seems irresolvable in human nature, our selfishness, our blindness, our abiding propensity for so much violence and cruelty.

Certainly, as Dylan later pointed out, the song conveyed a deep spiritual yearning. He had after all borrowed its melody from the classic African-American spiritual, “No More Auction Block,” which, according to Alan Lomax, originated among “[r]unaway slaves who fled as far north as Nova Scotia, after Britain abolished slavery in 1833.” And whatever its intent, the song was certainly adopted as an anthem of the Civil Rights movement, being played on the steps of the Lincoln Memorial the day King delivered his “I Have a Dream” speech and soon thereafter inspiring Sam Cooke’s own incredible anthem, “A Change Is Gonna Come.” In 1962, given Dylan’s immersion in protest politics, it likely was an expression of hope for change if not optimism. As Yarrow put it, “You can hear in this a yearning and a hope and a possibility and a sadness and sometimes a triumphal proclamation of determination. The answer is blowin’ in the wind means we will find the answer.” And yet, it certainly doesn’t carry the same triumphalism or confidence in the forward march of human progress as the following year’s “The Times They Are a-Changin’.” Perhaps, ultimately, the song works best as a series of timeless moral questions, leaving each of us in every new generation to provide an answer with our very lives.

8.) “Corrina, Corrina” (1962)

I got a bird that whistles
I got a bird that sings
But I ain’ a-got Corrina
Life don’t mean a thing

Despite a flurry of original songwriting in 1962-3, Dylan continued to lean heavily on folk and blues standards as sources of inspiration. Here with “Corrina, Corrina,” as Rolling Stone puts it, he demonstrated an early “ability to place folk music in a wider pop tradition,” taking a traditional song that Alan Lomax described as “a tender little blues with a touch of jazz and a flavor of hillbilly” and playing it “as a somber, pastoral ballad” of lost love with the barest bones of a band. The second verse (above) comes largely from blues legend Robert Johnson’s “Stones in My Passway,” only accentuating the song’s dual sense of desolation and rueful affection.

9.) “Tomorrow Is a Long Time” (1962)

There’s beauty in the silver, singin’ river
There’s beauty in the sunrise in the sky
But none of these and nothing else can touch the beauty
That I remember in my true love’s eyes

Suze Rotolo was Bob’s first flame in New York City and it was their on-and-off relationship (lasting all the way through early 1964) that provided the inspiration for a gaggle of gorgeous early songs Dylan wrote on love, longing, and loss, including this one, which he composed while Suze was studying art in Italy. According to Heylin, it was his “most personal song to date” and “first attempt to address heartbreak from an adult perspective.” Dylan later disparaged it somewhat, singling out the maudlin third verse (above), saying, “It’s pillow-soft, it’s not me… I don’t think that way.” And yet performers as diverse as Odetta, Elvis, and Rod Stewart didn’t seem to much mind its naked emotion, all taking a crack at the song’s “tender underside” before Bob finally released his original in 1971. Dylan would later come to regard Elvis’ bluesy 1966 version as “the one recording I treasure the most,” a sign of his enduring esteem for The King, while Stewart’s upbeat interpretation also deserves a listen. To my mind, Bob’s simple acoustic original still most effortlessly captures that sense of one young man’s “inconsolable loss.”

10.) “A Hard Rain’s a-Gonna Fall” (1962)

I heard the sound of a thunder, it roared out a warnin’
Heard the roar of a wave that could drown the whole world

It took me a while to “get” this song. It’s not exactly fun to listen to, but instead is heavy and jarring for a reason. Like so many later Dylan songs, it’s supposed to make us feel uncomfortable – it was a scary time, and still is. Perhaps Dylan’s own recollections from 1965 offer the best hint we have of the electric storm of feeling that brought forth this stunning prophetic screed: “I wrote it at the time of the Cuban crisis… We just hung around at night – people sat around wondering if it was the end, and so did I… It was a song of desperation. What could we do? Could we control the men on the verge of wiping us out? The words came fast – very fast. It was a song of terror.” Of course, as Heylin points out, the song was actually composed before the Cuban Missile Crisis, and yet there’s little doubt that Dylan’s thoughts at the time were pervaded by the sense of a world on the edge. As Evan Schlansky puts it, “[t]he song is like a road trip for the mind,” Bob’s “barbed wire voice” pummeling listeners with a torrent of horrifying and loosely connected images that speak to humankind’s stark vulnerability, greed, and vast destructive power. E.g, “I saw a newborn baby with wild wolves all around it, / I saw a highway of diamonds with nobody on it, / I saw a black branch with blood that kept drippin’, / I saw a room full of men with their hammers a-bleedin’…”

While Dylan adapted both the melody and refrain of the traditional Anglo-Scottish ballad “Lord Randall,” the song was also a dramatic departure from the folk and blues styles he’d become steeped in. As Heylin explains, “[‘Hard Rain’] smacked more of Ginsberg’s Howl or the speed-rapping of Kerouac – and it transformed Dylan into a folk modernist,” offering a preview of the surrealist imagery that would suffuse later albums like Highway 61 Revisited. It was also almost seven minutes long at a time when most pop songs were half that or less. Even the song’s message is hardly straightforward. It’s unclear what species of doom it foretells. Nuclear annihilation? Stateless anarchy? Environmental disaster? For Dylan it didn’t matter. His “Hard Rain” was not just supposed to be “the fallout rain,” he said. “I just mean some sort of end that’s just gotta happen.” But it serves as a warning as much as a prediction – of the dire consequences of continuing down the paths we are on. It’s clear by the song’s end that Dylan sees himself as a kind of fearless poet-prophet, willing to sacrifice his own life if it will get the word out. In the long final verse, the narrator’s mother asks her “blue eyed son” what he plans to do next and he responds, “I’m a-goin’ back out ‘fore the rain starts a-fallin’ / I’ll walk to the depths of the deepest black forest … / And I’ll tell it and think it and speak it and breathe it / And reflect it from the mountain so all souls can see it.” Almost 60 years later, Dylan may well still view himself as playing some version of that same prophetic role.

11.) “Ballad of Hollis Brown” (1962)

The rats have got your flour
Bad blood it got your mare
If there’s anyone that knows
Is there anyone that cares?

Having grown up in a small Midwestern mining town, Bob was likely familiar with the hardships of the rural poor. In this brutal ballad, eventually released on The Times They Are a-Changin’ (1964), Dylan unfurls the story of South Dakotan farmer Hollis Brown whose desperate poverty provokes him to murder his family and then himself. Set “to the tune of another ill-starred murder ballad [‘Pretty Polly’],” it’s clear, Heylin explains, that Dylan hoped to convey the “sense of a man driven to an unspeakable crime by the indifference of the world.” It was such weighty songs that gave his third album the reputation of being his most political, and yet this ballad is a protest without a solution. Using almost photographic details, Dylan simply beckons his listeners to feel the man’s despair. Unlike most ballads, as David Horowitz notes, this one is “told in the second person, present tense, so that not only is a bond forged immediately between the listener and the figure of the tale, but there is the ironic fact that the only ones who know of Hollis Brown’s plight, the only ones who care, are the hearers who are helpless to help, cut off from him, even as we in a mass society are cut off from each other.” Brutal indeed.

12.) “John Brown” (1962)

“But the thing that scared me most was when my enemy came close
And I saw that his face looked just like mine”

Bob’s live MTV Unplugged version of this song from 1994 is by far his best take on it, blowing the original 1962 bootleg out of the water. Like the tale of Hollis, “John Brown” is a relatively straightforward protest ballad, one that in this case highlights the horrors of war and tragic absurdity of mythologizing military service. Thematically similar to the Irish folk song “Mrs. McGrath,” it begins with a proud mother sending her son off to battle, instructing him to “Do what the captain says, lots of medals you will get / And we’ll put them on the wall when you come home.” It ends with the son returning perhaps a year later, maimed and scarred beyond recognition and utterly traumatized, dropping his medals into his mother’s hand before he turns to walk away. There’s nothing subtle about this anti-war tale, but man, it still packs a punch! Without minimizing the importance of military service, it emphasizes just what an immense sacrifice we are really asking of those we send to war.

13.) “Don’t Think Twice, It’s All Right” (1962)

I’m walkin’ down that long, lonesome road, babe
Where I’m bound, I can’t tell
Goodbye’s too good a word, gal
So I’ll just say fare thee well

Over his career, as Evan Schlansky puts it, Dylan has proven himself the master of “kiss-off” songs, and this gentle tune from The Freewheelin’ Bob Dylan (1963) was perhaps Bob’s first great one. It’s another of the songs of heartbreak he penned amid Suze’s extended stay in Italy in 1962, in fact probably “a direct response to the phone call [he received from her in August]… informing him that she would not be coming back around Labor Day as originally planned.” The melody comes from a Paul Clayton song, but the lyrics were Dylan’s own, masterfully building on “sweet and doleful finger-picking” and “cathartic, hillbilly harmonica” to convey the bitterness and sense of abandonment felt by the forlorn 21-year-old. The classic refrain suggests the narrator is attempting a kind of stoicism, though it’s plain to see he’s still hurting. With lines like “You just kinda wasted my precious time,” as Heylin explains, this is really the first time that Dylan’s “‘verbal bayonet’ comes out in song… Unfortunately for its author, his target remained three thousand miles away, enjoying her freedom from a rather possessive man.”

14.) “Walkin’ Down the Line” (1962)

I got my walkin’ shoes
An’ I ain’t a-gonna lose
What else can a poor boy do?

This upbeat tune depicts Bob in his element – “walkin’ down that long, lonesome road,” or in this case a train line. Per usual, our protagonist’s got a gal on his “troubled mind,” but here he also seems unable to stop the money from flowing “through the holes in the pockets of [his] clothes.” As blogger Tony Attwood observes, “everything is wrong” for our narrator, but it’s his “flying feet” that are “the cause of the upbeat nature of the song – he’s jogging along away from the latest misadventure.” “Walkin’ Down the Line” was hardly a major work for Dylan, but I’m still fond of it, perhaps because I can relate to the impulse to go walkin’ my blues away. It was another early Dylan song that never made a studio album and one he was content to let numerous artists cover, often poorly. My personal favorite is Sean Hayes’ 2004 version, which captures the simplicity of Dylan’s original, finally released in 1991. The archetype of the noble or tortured drifter is one Dylan will revisit countless times over his career, always holding onto hope that there’s some respite from the world to be found in life on the move.

15.) “Masters of War” (1963)

Like Judas of old
You lie and deceive
A world war can be won
You want me to believe

“Masters of War” is, shall we say, a tad heavy-handed – a “relentless, attacking dirge, pouring scorn and contempt on warmongers.”  Even Dylan admitted as much in the Freewheelin’ liner notes: “I’ve never really written anything like that before. I don’t sing songs which hope people will die, but I couldn’t help it in this one. The song is a sort of striking out… a feeling of what can you do?” But perhaps in the context of the Vietnam War, or any war, such desperate anger towards those in power – borne of anguish and fear – makes some sense. He certainly didn’t hold back. As Matt Melis writes, here Dylan is “putting the entire military-industrial complex on notice… [he] circles those who hide behind desks and in blood mansions like a vulture… until the final verse finds him promising: ‘I’ll stand over you grave / ‘Til I’m sure that you’re dead.’” Dark stuff! The tune, taken from veteran folksinger Jean Ritchie’s version of “Nottanum Town,” has a hypnotic driving rhythm that reinforces Bob’s dead-serious tenor.

16.) “Girl from the North Country” (1963)

Well, 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

In December 1962, Dylan took his first trip abroad for a couple gigs in London before heading on to Italy to try and track down his erstwhile lover Suze (who, it turns out, was already back in New York). While in London, Dylan hung out with English folksinger Martin Carthy and learned several new traditional songs, including “Scarborough Fair,” which would provide the melody for both “Girl from the North Country” and “Boots of Spanish Leather.” Despite the former’s explicit focus on a “north country” girl – presumably a reference to a childhood sweetheart – it’s likely that Dylan penned both with Suze in mind. As Heylin explains, “Girl from the North Country” is “as much of a requiem to his ‘lost’ true love as that ‘first’ love.” Though reminiscent of later works of nostalgic longing such as “Red River Shore,” it differs sharply in tone from the savage “kiss-off” songs that Dylan would write in the few years that followed. As Keith Richards put it, “there is an absence of Bob’s later cutting edge. There’s none of that resentment.” Although the original holds up beautifully, Dylan also recorded a reworked duet of the song with Johnny Cash for his 1969 country pop album Nashville Skyline.

17.) “Boots of Spanish Leather” (1963)

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

Unlike in the previous song, Dylan left little doubt here as to who he was writing about. As Matt Melis summarizes, this tender ballad “unfurls as a dialogue between two lovers, a woman setting sail for a trip overseas and a man remaining behind. The first six verses find her asking him what he might like her to send him as a souvenir, to which he continually insists that her safe return would be enough. Her suggestion that she might be gone for a long time, along with a letter she sends him… makes it clear to him that their love is over and that the gift is at worst a sort of buy-out to ease her guilt and at best a token to remember her by.” In the song’s final stanza, at last conceding that the relationship is doomed, Dylan’s narrator accepts the token, requesting that pair of “Spanish boots.” Although Dylan was actually able to convince Rotolo to move back in with him upon his return to New York, this beautiful song shows him “at his most open and vulnerable,” and offers a nice reminder – again relative to those later breakup songs gushing with bile and disdain – that Dylan was capable of being delicate and tender amidst heartbreak.

18.) “With God on Our Side” (1963)

Through many a dark hour
I’ve been thinkin’ about this
That Jesus Christ
Was betrayed by a kiss

Here Dylan hits some of the same thematic notes he did in “Masters of War,” serenading the leftie choir with a catalogue of state violence from the American-Indian Wars through the Cold War. “It is a living exposé of war crimes,” Tom Morello eulogizes, in which “Dylan lays bare the hypocrisy of war and unmasks the whitewashing of our military ventures.” Calling to mind Abe Lincoln’s dictum – “my concern is not whether God is on our side; my greatest concern is to be on God’s side” – the song highlights the dangerous assumptions and pretenses that have so often been used to justify armed conflict. Has Dylan “crossed the line,” as Heylin suggests, coming a little too close to a dull, judgy sermon? Perhaps. But as a lifelong churchgoer myself, perennially disgusted by the Religious Right with its theocratic tendencies and fervent embrace of militarism, I have to say: this still hits home.

19.) “When the Ship Comes In” (1963)

Then the sands will roll
Out a carpet of gold
For your weary toes to be a-touchin’

“Even as a twenty-one-year-old lapsed Jew,” Heylin writes, Dylan “seemed to believe in an actual Judgment Day.” Although he was prompted to write this song after initially being refused service at a hotel in August 1963 due to an “unkempt appearance,” in Dylan’s fiery imagination it quickly grew into “a sprawling epic allegory about vanquishing the oppressive ‘powers that be’,” complete with a host of bizarre almost-Biblical images (“seas will split… fishes will laugh… [rocks] will proudly stand”) heralding the new world order. His lyrics also took inspiration from “Jenny’s Song,” featured in Bertolt Brecht and Kurt Weill’s Threepenny Opera. Heylin explains: “As Pirate Jenny dreams of the destruction of all her enemies by a mysterious ship, so Dylan envisages the neophobes being swept aside in ‘the hour when the ship comes in’.” Although the song certainly began as a kind of David versus Goliath “revenge fantasy,” Dylan clearly felt it had a broader social meaning, being one of two songs he performed at the March on Washington. Curiously, the motif of the symbolic “ship” of judgment would reappear in two important post-conversion compositions, namely “Caribbean Wind” and “Jokerman”.

20.) “The Times They Are a-Changin’” (1963)

Come mothers and fathers
Throughout the land
And don’t criticize
What you can’t understand

Despite dripping with syrupy idealism, this archetypal protest anthem has meant too much to me over the years not to include it on this list. I can still remember how it warmed my breast with a sense of hope and possibility for the future when I heard it performed in college at rallies and marches, just as it must have done for Dylan’s early fans in the protest movements of the early 1960s. As the title track to his third album, it was the direct successor to “When the Ship Comes In” but is “altogether more self-conscious” – Bob reportedly told a friend at the time that he wrote it because “it seems to be what the people want to hear.” In that much he was right, although he would soon shift away from such overt expressions of idealism. “We often think of young Dylan as a boy with an old soul, but these lyrics aren’t wizened. They’re undeniably naïve,” writes Monica Hunter-Hart. And yet Bob still “pulls it off, capturing the optimism of both his budding generation and all youth movements since.”

In some sense, the song merely states the obvious, that even though much that is human stays the same, important things do change from generation to generation as the baton of “progress” gets passed down the ages. Like “Blowin’ in the Wind,” it is a song that has become, as Peter Yarrow put it, “part of the secular liturgy of our times.” It even draws on Biblical language, quoting Mark 10:31 in its final stanza: “But many that are first shall be last, and the last first.” It has been covered by a laughable array of musicians, including Simon and Garfunkel, The Beach Boys, The Byrds, Odetta, Cher, The Hollies, Nina Simone, Josephine Baker, James Taylor & Carly Simon, Billy Joel, Tracy Chapman, Richie Havens, Phil Collins, Bruce Springsteen, and Brandi Carlile. Despite its association with protest movements, Dylan has also oddly licensed the song to be used for various corporate purposes, including commercials for Macintosh, Coopers & Lybrand, and the Bank of Montreal.

As one of his last compositions before JFK’s assassination in November, “Times” would also play a role in a major thematic turning point in Dylan’s career at the end of 1963. Heylin argues that the song’s political optimism – “[t]hat inchoate feeling, bound up with a new order he felt was just around the corner, dissipated with the dawn of [that] particularly fateful Friday.” The night after Kennedy was shot, Dylan had to open a show in upstate New York with this new anthem, but as he later told biographer Anthony Scaduto, its idealism suddenly seemed misplaced: “I thought, ‘Wow, how can I open with that song? I’ll get rocks thrown at me.’ But I had to sing it, my whole concert takes off from there. I know I had no understanding of anything. Something had just gone haywire in the country and they were applauding the song. And I couldn’t understand why they were clapping, or why I wrote the song.” Before long, Dylan would largely turn his back on these kinds of straightforward crowd-pleasing protest songs in his writing and begin casting out in new artistic directions. More than 30 years later he would also win an Oscar for a song with a very different message: “I used to care, but things have changed.”

21.) “Lay Down Your Weary Tune” (1963)

I stood unwound beneath the skies
And clouds unbound by laws
The cryin’ rain like a trumpet sang
And asked for no applause

In this gorgeous hymn-like tune, Dylan sets aside all of his recent striving and bids listeners to take spiritual refreshment in the freely-given music of nature, which “no voice can hope to hum” and which needs “no applause.” As Michael Gray describes, it’s “a vision of the world… in which nature appears not as a manifestation of God but as containing God in every aspect,” echoing the mystical poetry of one of Dylan’s own favorites, William Blake. Robert Shelton called this Bob’s “first withdrawal song,” written in the fall of 1963 during a “sojourn in peaceful country” at Joan Baez’s house in California. Inexplicably, he chose to leave it off The Times They Are a-Changin’, relegating the track to obscurity until it was finally released on 1985’s Biograph. According to Heylin, even though “Lay Down Your Weary Tune” was “clearly the superior composition” and “[a] perfect album closer, it was superseded by ‘Restless Farewell,’” a song Dylan used to get back at Newsweek for an unfavorable article.