Desolation Revisited: A Moderately Insane 120-Song Bob Dylan Playlist for Dark Times, Pt. 2/7

Hey folks! This is a passion project I started working on a few months ago and then took a break from for awhile. I’m still a LONG way from finishing the whole annotated playlist and can’t say when I’ll be done with it, but if you want to know the context and motivation behind the project or check out part 1 (1961-1963), you can do that here. Anyway, hope y’all enjoy part 2 – it begins with an intro describing Dylan’s life during the time period…

II. 1964-1966

By the end of 1963, Bob Dylan had risen to folk stardom on the backs of political songs like “Blowin’ in the Wind” and “A Hard Rain’s a-Gonna Come” – but this newfound fame brought with it all manner of new expectations and distractions for the 22-year-old. As Heylin explains, “when the Peter, Paul, and Mary version [of ‘Blowin’ in the Wind’] rose to the top of the charts in the summer of 1963, it began to tear apart its author’s cozy world. Dylan soon began to be pestered by those who thought that anyone asking such questions had the answers.” Over time he came to resent this “spokesman” role and being pigeonholed as an acoustic-only “protest singer,” and grew increasingly jaded with the kind of “fish in a barrel” topical songs that dominated his output in 1963 – and his third album, The Times They Are a-Changin’. By 1964, Dylan’s songwriting style was already heading in a new direction, a shift he later attempted to explain in an interview in November 1965:

Before, every song had to have a specific point behind it, a person, a thing. I would squeeze a shapeless concept into this artificial shape… I used to have to go after a song, seek it out. But now, instead of going to it, I stay where I am, and let everything disappear, and the song rushes to me. Not just the music, the words, too… I was still keeping the things that are really real out of my songs, for fear they’d be misunderstood. Now, I don’t care if they are.

His fourth album, appropriately titled Another Side of Bob Dylan (1964), gave the broader public its first taste of this new approach – one in which Dylan was far less intent on being socially conscious or narratively or thematically straightforward. Among an array of influences, Dylan became enamored that year with 19th-century French Symbolist poet Arthur Rimbaud, whose work had also inspired the Surrealist and Dadaist movements. According to Rimbaud, “the poet makes himself a seer by a long, prodigious and rational disordering of the senses,” an artistic vision that Dylan would come to embrace over the next two tumultuous years.

Another Side was a transition album. Dylan had penned numerous songs of introspective or romantic nature for prior records, but now such deliberately apolitical content predominated. He was clearly “trying to escape his image as Mr. Political Statement.” One of the most notable tracks, “My Back Pages,” served as a direct rebuke to his most fervent folkie fans and a conscious uncoupling from the movements that had made him famous. A number of songs also dealt with Dylan’s final explosive breakup with Suze that spring, a split precipitated in part by her experience having to procure an abortion a few months before and Bob’s ongoing affair with fellow folk icon Joan Baez. According to witnesses, Suze, Dylan, and Suze’s sister Carla fought like cats and dogs that night in March when they parted ways. As Howard Sounes recounts, “The scene became hysterical, with Bob and Suze screaming at each other into the early hours of the morning… Bob refused to leave. Carla pushed him. He pushed back… Friends were called and finally Bob was forcibly removed.” Dylan took the breakup hard. As he told Robert Shelton in 1966, “After Suze moved out of the house, I got very, very strung out for a while.”

By several accounts, Bob began experimenting more with hard drugs (including LSD), while continuing to tour, travel, and party at an exhaustive pace. Many of his Another Side songs were completed during a brief respite with Nico in Greece in late May. As Schlansky puts it, despite garnering mixed reviews, “The album captures a brief moment in time before his writing evolved into a swirl of grotesque and surrealist imagery, yet was more reefer-and-Rimbaud-fueled than his previous efforts.” Dylan’s open defiance of expectations certainly caused some consternation among fans – the editor of Sing Out! accused him of having “lost touch with the people” – but no one could have predicted just how musically far afield Dylan would yet travel, or how much fan rage he would face.

In the summer and fall of 1964, he slowed down his pace of travel, and started experimenting with producers and fellow musicians on new electric sounds, while spending countless hours hunched over his typewriter taking stabs at his own brand of surrealist, stream-of-consciousness beat poetry. These efforts culminated first in the blockbuster release the following March of Bringing It All Back Home (1965) – the first of his Electric Trilogy – a half-acoustic, half-electric album that opened with Dylan’s dizzying proto-rap song, “Subterranean Homesick Blues,” his first top-40 hit and an outlandish opening statement of his bold new style. It would prove to be only the tip of the iceberg.

While there had certainly been prior signs of Bob’s dazzling songwriting potential, in 1965 the creative floodgates flung wide open. Heylin puts it best:

Superlatives fail and comparisons disappear in a blizzard of inspiration. The Dylan of 1965 was making the most direct, powerful, and artistically important song-statements of the twentieth century. At the absolute epicenter of popular culture for an eighteen-month period when he, and he alone, was in the unknown region, he returned with regular bulletins of prophetic perspicacity. The thirty songs recorded in those twelve months, even in stark isolation, would make him the single most important singer-songwriter of the postwar era.

Over his next two albums, Dylan’s beautiful, baffling poetry exploded in every direction within the new amped-up rock-and-roll format as he unleashed the unruly force of his mind and full nasal sneer, peppering listeners with an often-bewildering array of “visual impressions,” “crypto-poetic diatribes,” and “strange psychedelic musings.” During a magical and grueling year and a half, Dylan invented whole new species of rock, translated beat poetry into mainstream music, and composed some of the greatest songs ever written, including “Like a Rolling Stone,” “Desolation Row,” and “Visions of Johanna.” In the process, he changed music forever.

Of course, Dylan also pissed a lot of people off. Beginning with the infamous electric set at the Newport Folk Festival in July 1965 – in which his deafening performance of just three songs was met with “a chorus of shouts and boos” – Dylan’s relationship with fans and the press turned increasingly contentious and combative. Backed by The Band (then known as The Hawks), who he later referred to as his “gallant knights,” Bob’s defiant part-acoustic, part-electric performances through the rest of 1965 stoked ever greater controversy, as more of his possessive folk fans – convinced their hero had betrayed his folk and political roots – began to make their feelings known. Tensions finally boiled over during the Bob Dylan World Tour of 1966, “one of the most notorious music tours ever staged,” in which Bob and his backing band faced almost nightly throngs of angry spectators during 47 raucous shows between February and May. “It was like we went through the war together,” lead-guitarist Robbie Robertson later said. But despite the toll, they refused to back down. As Robertson explained,

When people boo you night after night, it can affect your confidence. Anybody else would have said, “Well, the audience isn’t liking this, let’s change what we’re doing.” We didn’t budge. We went out there… and the more they booed, the louder we got. Inside of us we felt, “This is a revolution. And we’re part of this revolution, and we’re going to go through with it.”

In the end, Bob and his “gallant knights” were right. They were part of a cultural revolution. Although many of his greatest works were still to come, it is likely that those three 1965-66 albums are the ones the Nobel Committee most had in mind when they awarded Dylan a Nobel Prize for creating “new poetic expressions within the great American song tradition.” Building on Bringing It All Back Home, Highway 61 Revisited (1965) and Blonde on Blonde (1966) broke all the molds, but in the process, this period of feverish creativity almost broke Bob. As blogger Tony Ling writes, “One can only imagine the psychic blows he took every night in 1966, high as a kite and being booed for making incredible music.” Had a mysterious motorcycle accident in July 1966 not halted his Icarus-like ascent and forced him to take stock of the damage he was inflicting on his own mind and body, there’s no telling how it all would have ended, but not well.

22.) “Mr. Tambourine Man” (1964)

I’m ready to go anywhere, I’m ready for to fade
Into my own parade, cast your dancing spell my way
I promise to go under it

Dylan experienced a brief burst of creativity in early 1964, composing a couple innovative and densely poetic songs including this ode of “youthful wonderment” inspired by his trip to New Orleans for Mardi Gras that February. It’s been described as “the Bob Dylan song even your grandma could love; featuring a flowing, pretty and engaging melody, vocals unobscured by grit… and words that soothe and beckon instead of divide.” Although he did not release it until March the following year, “Mr. Tambourine Man” would become one of Dylan’s biggest hits, and in the hands of The Byrds, the lone No. 1 song of his career. Byrds’ singer David Crosby later contended that it was perhaps “the first time anyone put really good poetry on the radio… I think [Bob] was finding himself as a poet.”

Apparently written after a bout of “intense exhaustion following a Mardi Gras celebration,” the song’s swirling lyrics call on the mysterious title character to play a tune that will sweep its world-weary narrator away to a place “[f]ar from the twisted reach of crazy sorrow.” As William Ruhlmann explains, “The time seems to be early morning following a night when the narrator has not slept. Still unable to sleep… he is available and open to Mr. Tambourine Man’s song, and says he will follow him.” While the alluring title character has been variously interpreted as representing Dylan’s muse, a drug dealer, a mystical Pied Piper or Christ-like figure, or even some specific musical inspiration such as Bruce Langhorne (or Dylan himself?), he is, in any event, someone who at least seems to afford our benumbed narrator a spiritual reprieve from the suffering of the world. In this sense, the song offers a widely resonant message about finding transcendent beauty amid life’s seeming emptiness, perhaps bringing to mind Rumi’s exhortation to “Let yourself be silently drawn by the strange pull of what you really love. It will not lead you astray.” As a bizarre footnote, the song was also one of Hunter S. Thompson’s favorites, played at his funeral in 2005 as Hunter’s ashes were shot from a cannon.

23.) “Spanish Harlem Incident” (1964)

Let me know, babe, about my fortune
Down along my restless palms

This is one of those Bob Dylan songs I have trouble explaining why I love so much – it just has a way of implanting itself in my mind for days on end. Described by Rolling Stone as “[o]ne of Dylan’s most open, unambiguous sex songs,” it was the third track on 1964’s Another Side of Bob Dylan and one he only ever played once in concert, in October of the same year. Like the album on which it was featured, “Spanish Harlem Incident” shows Dylan in the midst of a lyrical transition, having, as one blogger points out, “one foot in the surreal world of the Electric Trilogy and one foot in the more conventional lyrical styles of the acoustic albums.” The “incident” that the song recounts “seems to be as tiny as incidents come: the ‘gypsy gal’ holding his hand in hers, and sparking a flurry of associations.” As Heylin explains, “There is no verbal suggestion that this spellbinding lady is doing anything but reading the narrator’s fortune. Still, he allows himself to fall hopelessly under her spell.”

24.) “It Ain’t Me Babe” (1964)

Go lightly from the ledge, babe
Go lightly on the ground
I’m not the one you want, babe
I will only let you down

“It Ain’t Me Babe” is one of a handful of songs Dylan penned in the spring and summer of 1964 dealing at least in part with his brutal breakup with Suze that March. As Heylin explains, “After writing a couple of songs in February that opened up a whole new approach to songwriting… he was distracted by [the breakup]… [and] poured his feelings into songs of heartbreak (‘Mama You Been on My Mind’), paranoia (‘Ballad in Plain D’), and a yearning for lost intimacy (‘To Ramona’).” This one clearly falls somewhere in that mix. Although a few critics have also read the song as an allegorical “farewell to folk and acoustic music” or a “commentary on blind patriotism,” on its surface “It Ain’t Me Babe” is another one of Dylan’s classic “jilted lover’s kiss-off” songs, a “spiritual cousin” to earlier ones like “Don’t Think Twice, It’s Alright” and later ones like “Positively 4th Street.”

What resonates most with me is its narrator’s frank insistence that he cannot be whatever idol or savior his apparently co-dependent lover has dreamed him up to be. While in the real world it was Suze who initiated their breakup, here we find the tables turned as an emotionally invulnerable male narrator asserts his autonomy from a rather possessive lover, highlighting a common Dylan theme of “desire for love but on his own terms.” As Matt Melis adds, “one characteristic we see from his earliest days is his unwillingness to wear shackles of any type – whether the irons be politics, public perception, musical genre, or love. It ain’t for him, babe.” Such commitment aversion may not exactly be the most noble of traits, but at least it is in some sense honest or realistic, though still accompanied by a heavy dose of Dylan’s “trademarked bitterness.” Shortly after the song’s release, Dylan-admirer Johnny Cash put a twist on the song, recording a hit version as a duet with his future wife June Carter.

25.) “Mama, You’ve Been on My Mind” (1964)

Even though my mind is hazy an’ my thoughts they might be narrow
Where you been don’t bother me nor bring me down in sorrow
It don’t even matter to me where you’re wakin’ up tomorrow
But mama, you’re just on my mind

Bob was definitely having some feelings in the spring of 1964. As previously noted, this “straightforward love song of separation and yearning” was one of a number Dylan wrote in the aftermath of his split from Suze, and yet according to Heylin it’s the best of the lot, making it “more than a little perverse” that Bob chose not include it on Another Side of Bob Dylan. While I personally prefer “To Ramona,” Dylan certainly gets his point across beautifully in this wistful tune, with its “gorgeous melody and cascading, almost incantatory lyrics” (as Oliver Trager put it). The words are so simple, and yet it’s hard to imagine a better way he could have captured that painful inward struggle we often face of not quite being able to let someone go after a breakup, continually eaten up by regret and longing and looped replays in our minds of key moments over the course of a doomed relationship. Dylan eventually released several versions of this song on his Bootleg Series, but it’s been covered widely, including by Bettye LaVette, George Harrison, Jeff Buckley, Joan Baez, Johnny Cash, and Rod Stewart.

26.) “To Ramona” (1964)

But it grieves my heart, love
To see you tryin’ to be a part of
A world that just don’t exist
It’s all just a dream, babe
A vacuum, a scheme, babe
That sucks you into feelin’ like this

I don’t share Jackson Browne’s conviction that this song of “rueful resignation” is somehow also about the Civil Rights movement – “as clearly as a James Baldwin novel” – but it certainly contains some of Dylan’s most evocative and elegantly-crafted lyrics and does seem to place immediate romantic matters in a larger context of how we relate to and exist in the world around us. As Browne writes, “It is a song imbued with the struggle for personal freedom and the perpetual trap of co-dependence. This was a moment when people wanted a leader and spokesman. But in this song, Dylan dismantles that: ‘I’d forever talk to you / But soon my words / They would turn into a meaningless ring.’ He’s always an advocate for finding your own way.” Unlike several other Dylan post-breakup songs from the period, this one lacks much bitterness or resentment; instead, as Schlansky puts it, Bob’s “empathy for a girl caught between forces, fixtures and friends is palpable.” While the original needs no changing, a beautiful live version of this song by David Gray was included on his 2007 album, A Thousand Miles Behind.

27.) “I’ll Keep It with Mine” (1964)

You will search, babe
At any cost
But how long, babe
Can you search for what’s not lost?

Dylan did eventually get all of those songs of heartbreak over Suze out of his system in 1964, but he didn’t immediately stray too far in subject matter, as illustrated by this plaintively affectionate tune he wrote for Christa Paffgen – or Nico – his female traveling companion in Europe that May. As Heylin observes, Nico was an “aspiring actress [from Germany] who had been obliged to take up modeling to make ends meet… Dylan’s undoubted attraction to the imperious ice maiden cannot come as any great surprise… Yet allowing her to accompany him all the way down to Greece when he had an album to [complete] suggests he yearned for some female companionship.” The song may also in part have been inspired by Nico’s young son, who accompanied them on the trip – she later contended that Bob had written it “about me and my little baby.” Although the lyrics are somewhat enigmatic, this may help explain some of the benevolent paternalism that seems to pervade them. According to Paul Cable, “the lyrics form the least patronizing way I have yet heard of saying, ‘I’m older than you – therefore I know better.’” Unfortunately, “I’ll Keep It with Mine” proved to be yet another underappreciated gem that Dylan neglected to include on a studio album, instead letting Nico herself record a rather grating version for her 1967 album Chelsea Girl, before finally releasing his exquisite stripped-down original on Biograph (1985).

28.) “My Back Pages” (1964)

“Equality,” I spoke the word
As if a wedding vow
Ah, but I was so much older then
I’m younger than that now

“My Back Pages” was likely the last song Dylan wrote for Another Side of Bob Dylan and its most politically provocative. After spending much of the spring preoccupied with the Suze split, we now find him reflecting on a different sort of breakup – publicly disowning the idealism that had fueled so many of his earlier hits and the movements that helped make him famous. Cameron Wade writes, “Though Dylan wouldn’t excommunicate himself from the folk scene until he went electric at the 1965 Newport Folk Festival, ‘My Back Pages’ was his public dismissal of his old identity as the de facto spokesman for the deeply entwined folk and protest movements… a harsh self-examination that single-handedly obliterates the first stage of Dylan’s career.” The lyrics unmask Bob’s thorough disillusionment with the old “lies that life was black and white” and the “soldier’s stance” that had caused him to “become my enemy / In the instant that I preach.” Dylan laments the self-importance of his “older” former self – how he “dreamed / Romantic facts of musketeers” and stood guard over “abstract threats / Too noble to neglect” – and does little to hide his disdain for all the “corpse evangelists” who still do. By 1964, as blogger Tony Ling concludes, Dylan “had seen how hard changing the world really is… [and] realized that the world is not just about Issues and Politics… he saw that there’s as much of the world in love, and in music, and in everything that we take for granted but means so much more when you get right the hell down to it.”

29.) “It’s Alright, Ma (I’m Only Bleeding)” (1964)

As human gods aim for their mark
Make everything from toy guns that spark
To flesh-colored Christs that glow in the dark
It’s easy to see without looking too far
That not much is really sacred

There have been times looking back over Dylan’s career when it seems like he truly caught lightning in a bottle, when a kind of inspiration-from-beyond took up residence in his soul just long enough to find expression. Singling out “It’s Alright, Ma,” Dylan himself tried to explain as much to Ed Bradley in 2004: “I don’t know how I got to write those songs… Try to sit down and write something like that. There’s a magic to that, and it’s not Siegfried and Roy kind of magic, you know? It’s a different kind of a penetrating magic.” This song definitely contains some of the most memorable poetry of Dylan’s career, with lines like “he not busy being born is busy dying” or “even the president of the United States / Sometimes must have to stand naked,” and yet its chief purpose is clearly to unsettle.

As in “A Hard Rain’s a-Gonna Come,” Dylan has again made himself a conduit for dark prophetic truth, standing “outside society” as he pummels listeners with a torrent of withering insights and precious little uplift over fifteen verses. Like “Holden Caulfield on acid,” this narrator sees corruption and phoniness everywhere he looks – politics, religion, commerce – suggesting a level of “futility absent from earlier songs.” As Monica Hunter-Hart puts it, “Dylan doesn’t just expose the world’s darkness here; he reveals the ubiquity of that darkness.”

And yet, in the midst of such apocalyptic gloom, our clear-eyed protagonist asserts his own bleak freedom, brushing “off absurdity and pain (‘it’s alright’) because it’s normal.” As Heylin writes, “It seems [Dylan] had finally got around to reading Sartre and Kierkegaard, for here is the first evidence of an existential strain that suffuses much of [his later work].” Several verses towards the end of the song make this influence readily apparent, with lines like “Although the masters make the rules / For the wise men and the fools / I got nothing, Ma, to live up to.” Ultimately, while it preceded Dylan’s jump from acoustic to electric, this astonishing poetic screed from late summer of 1964 inaugurated a new lyrically-liberated kind of songwriting that would permeate his next three incredible albums.

30.) “Maggie’s Farm” (1965)

Well, he hands you a nickel
He hands you a dime
He asks you with a grin
If you’re havin’ a good time
Then he fines you every time you slam the door

My first encounter with this song was the smoldering heavy-metal cover version on Rage Against the Machine’s Renegades (2000), and it has struck me ever since as a potent expression of working class rage. In fact, Dylan’s original was inspired by the folk song “Down on Penny’s Farm” – about the plight of sharecroppers – but it’s unclear exactly what “farm” bosses Dylan was raging against in early 1965. I’m sure, as usual, he had no shortage of targets. As Hilary Saunders writes, “It’s been said Dylan was fighting the Man, the service industry, the music industry, the military institution or even the previous iterations and perceptions of his persona.” But it doesn’t matter much. The song became a “war cry” for the counterculture – kids who, as Dylan wails, had a “head full of ideas” but were still stuck having to “[s]crub the floor.” Notably, it also ushered in his controversial “electric” phrase as the first song he played for his infamous earsplitting 1965 Newport Folk Festival set. (Production manager Joe Boyd later claimed the “first note of ‘Maggie’s Farm’ was the loudest thing anybody had ever heard.”) The song also showcases Dylan’s oft-maligned “sand and glue” voice in its full nasally glory, as defiantly unconstrained here as his songwriting itself would be in this glorious season of creativity.

31.) “Like a Rolling Stone” (1965)

Princess on the steeple and all the pretty people
They’re drinkin’, thinkin’ that they got it made
Exchanging all kinds of precious gifts and things
But you’d better lift your diamond ring, you’d better pawn it babe

What can you say about perhaps the greatest rock song of all time? Of all the other classics Dylan has penned, none comes close to touching this one. It’s been variously described as a “thunderous six-minute rock epic,” “one of the most self-righteous and eloquent indictments ever committed to wax,” “a rock and roll institution, a declaration of independence… a cosmic romp through interior streets,” and much more. My favorite reflection comes from Springsteen, who recalled having a “religious experience of sorts” when he first heard the song at age 15: “I was in the car with my mother listening to WMCA, and on came that snare shot that sounded like somebody’d kicked open the door to your mind.” That’s what it felt like, even for me, first hearing it in the late 1990s – I was immediately overcome with a sense of awe and connection, swept up in a dream of vindication that felt like balm for my tortured, insecure teenage soul. “You can taste the bile rising up in his throat,” Robert Ham writes, and it was delicious.

Like “It’s Alright, Ma,” this was one of those songs over which, at least by Dylan’s reckoning, he “exercised very little conscious will.” As he told Robert Hilburn, “It’s like a ghost is writing a song like that. It gives you the song and goes away. You don’t know what it means. Except that the ghost picked me to write the song.” This blistering tale of a “fallen society princess” began as a “piece of [poetic] vomit about twenty pages long” that Dylan scrawled out in a fit of inspiration after an exhausting overseas tour in May 1965 – it was then honed over a couple weeks “down to four spiraling, spitting verses that culminate in that insistent chorus.” In mid-June, as Heylin explains, Dylan showed up “at Columbia’s Studio A ready to create a thing called rock music in a single afternoon.”

This was no dainty 3-minute pop jingle of the sort that still dominated the charts in 1965 – other chart-topping performers that year included The Beatles, The Supremes, The Beach Boys, The Four Tops, The Righteous Brothers, Sonny & Cher, and Herman’s Hermits. This was something much more visceral than all that, a song that doled out more raw disdain and retribution than anything else. As Bono writes, “It’s a black eye of a pop song… This is Dylan as the Jeremiah of the heart. Having railed against the hypocrisies of the body politic, he starts to pick on enemies that are a little more familiar: the scene, high society, ‘pretty people’ who think they’ve ‘got it made.’ … The tumble of words, images, ire and spleen on ‘Rolling Stone’ shape-shifts easily into music forms 10 or 20 years away, like punk, grunge or hip-hop.” Indeed, it kicked open the door to all kinds of less-inhibited forms of poetic expression in music. Here’s Springsteen again: “The way that Elvis freed your body, Dylan freed your mind, and showed us that because the music was physical did not mean it was anti-intellect.”

“Like a Rolling Stone” became the most successful single of Dylan’s storied career, reaching No. 2 on the charts behind only The Beatles’ “Help!” as the first single off Highway 61 Revisited (1965). (Amazingly, Dylan has never had a No. 1 hit of his own.) And yet its release was not without controversy. Columbia initially balked at putting it out, hesitant over the song’s length and new electric sound. At more than six minutes long, it was twice the length of the standard three minutes allotted for singles on the radio in those days. But after it was leaked to influential DJs in July, “Rolling Stone” began to take on an unstoppable momentum as jockeys rapidly abandoned “their pre-conceived notions of how long a radio single could be, paving the way for freeform radio.” There’s no doubt that the song changed the course of music history. According to Rolling Stone – the rock magazine named in part as an homage to this very song – “No other pop song has so thoroughly challenged and transformed the commercial laws and artistic conventions of its time, for all time.”

As “savage a cry of ‘Fuck off’ as exists in the annals of popular song,” Dylan went on to perform his electrifying rock archetype with all the defiant relish it deserved night after night on his famously contentious 1966 World Tour, not knowing that his own career would come to a crashing stand-still just a few months later. It’s perhaps worth noting that, for all its vitriol, “Like a Rolling Stone” is not completely without heart. Dylan ultimately seems to suggest that Miss Lonely’s crushing fall from grace still presents a kind of opportunity – a chance to start over, to see more clearly, to live more freely, to regard with humility those she had long ignored. The song offers, as Robert Shelton contends, a faint “compassion for those who have dropped out of bourgeois surroundings… Myths, props, and old beliefs fall away to reveal a very taxing reality.” Listening to a song like this makes you wonder whether Dylan – so skillful and ruthless at tearing others down – might someday turn that incisive, acerbic wit on himself. Indeed, he eventually would. But in a larger sense, this rousing morality tale also speaks to us all of the illusoriness of our illusions – the fundamental pretense of all our wealth and fame and success – and thus anticipates not only the dark valleys of Dylan’s own life and career, but our own inevitable ones as well. As blogger Jacob Smith writes, “We are all three days away from being tabloid news. And most of us are on day two.”

32.) “Tombstone Blues” (1965)

The ghost of Belle Starr she hands down her wits
To Jezebel the nun she violently knits
A bald wig for Jack the Ripper who sits
At the head of the chamber of commerce

For a long time, I struggled with these more surrealist songs from Dylan’s Electric Trilogy – it just wasn’t my cup of tea. The lyrics felt so jumbled, so opaque, so patently absurd, that I assumed it was all some kind of drug-fueled nonsense. And I’m sure Bob’s not entirely above writing a little artful nonsense, even if he is a Nobel Laureate – look at the verses on “You Ain’t Goin’ Nowhere,” for instance. Still, the more you ruminate on songs like “Tombstone Blues,” the more you can sense what he was on about. As in other classics of the period, Dylan depicts an unsettling “melee of totally unrelated events involving totally unrelated weirdo characters.” Among those in this particular “madcap menagerie,” Heylin writes, we encounter “the likes of Paul Revere’s horse (though not Revere himself), Belle Star…, Jack the Ripper (now enough of a worthy to join the Chamber of Commerce), John the Baptist (who is torturing a thief—possibly in the night), and Gypsy Davey (who carries a blowtorch, in case the ‘glamor’ doesn’t work).” By song’s end, it’s hard to say what exactly ties all these culturally iconic characters together except that they’re clearly involved in something sinister.

What I love most about this song is how it radiates chaos – how the elements combine to make you feel like you’re part of something dangerously out of control, perhaps about to explode, like you might need to run for it. It’s the most energetic track on Dylan’s most electric of albums, backed by a “driving groove that threatens to fly off the rails at any moment.” The lyrics paint a bleak surrealist portrait of a desperate family in the midst of a world that’s utterly corrupt and governed by violence and deceit. As one fan site commenter put it, it’s like a rock interpretation of Brueghel’s “Triumph of Death” – “all these symbolic or mythological characters… are busy in their useless fights, endeavors, debates, tricks and cheats, etc., while ordinary people are starving and nobody cares.” According to Rolling Stone, “Dylan claimed this breakneck jeremiad against violence-gorged American political culture was influenced by conversations he heard at a bar that was frequented by police officers. ‘They’d be saying stuff like, ‘I don’t know who killed him, but I’m glad he’s gone’…’ [Dylan] said. That murky yet matter-of-fact sense of lawless brutality and systemic evil infuses [the] lyrics.” Ultimately, even if we can’t make sense of every line, this song gets its point across – and rocks in the process.

33.) “Desolation Row” (1965)

And the only sound that’s left
After the ambulances go
Is Cinderella sweeping up
On Desolation Row

“What does one do the month after inventing an entirely new form of popular song?” Heylin asks. “One does it again.” Just weeks after recording “Like a Rolling Stone,” Dylan penned this 11-minute masterpiece likely inspired by a wide array of influences – from Kafka, the Beats, and T.S. Eliot’s The Waste Land to scenes from Bob’s own Greenwich Village neighborhood. Once again, we find him playing a kind of dark surrealist painter “placing familiar characters in disturbingly unfamiliar scenarios.” It’s another of those songs that seem to embrace T.S. Eliot’s notion that poetry should “communicate before it is understood.” As with “Tombstone Blues,” there is no unifying narrative here, only a series of evocative, jarring vignettes that build over ten verses to create a chaotic atmosphere and general theme of desperation and human frailty.

Bob’s motley crew of cultural icons includes numerous historical, biblical, fictional, pop culture, and literary figures, all “crammed together” in an unspecified alternate universe on Desolation Row. Yet, despite its grim dystopian backdrop – “They’re selling postcards of the hanging… / And the riot squad they’re restless” – the events of the song are not exactly apocalyptic. As Schlansky explains, these characters seem in some sense to “get along fine. The Phantom of the Opera communes with Casanova, Einstein disguises himself as Robin Hood, and Cinderella, who flirts with Romeo, resembles Bette Davis.” Upon first listen, it’s hard not to assume this is all artful nonsense, and indeed, as Heylin contends, “one must be wary (as others have not been) of reading too much into Dylan’s name-dropping.” But there’s much method in his lyrical madness: “these familiar cultural icons… provide him with a series of archetypes he can place in his own wasteland… [“Desolation Row” is] an aural painting… something like Bosch’s Garden of Earthly Delights, a triptych vision of heaven and hell.”

What ties all these characters together is their neediness, brokenness, and desperation, what Anne Lamott calls the “slimy and pathetic” stuff of human nature. No matter how ostensibly famous or revered they may be, all seem to be engaged in the same debased search for escape in this “totalitarian world,” only available on “the ominously named Desolation Row.” As Dylan famously sings, “except for Cain and Abel and the Hunchback of Notre Dame / Everybody is making love or else expecting rain.” Even the Good Samaritan is “going to the carnival tonight.” It’s a bleak vision, for sure, but there’s also something beautiful in how we are united in disgrace on this sleazy avenue. I don’t think I really understood “Desolation Row” or perceived anything of myself in its “Fellini-esque parade of grotesques and oddities” until I had truly experienced desolation of my own, until I understood how rife with pretense our civilized world and our own well-orchestrated lives can be. Now it’s one of my all-time favorites.

34.) “Positively 4th Street” (1965)

You say you lost your faith
But that’s not where it’s at
You had no faith to lose
And you know it

There are a number of heartbreak songs on this list that offer glimpses of Dylan’s softer, more vulnerable, perhaps even compassionate side. This is emphatically not one of them. It’s as much a song of hate as lost love – one of the ultimate Dylan “kiss-off” songs, seething with disdain and contempt towards a presumably ‘faithless’ ex-lover or friend. As with “Like a Rolling Stone,” it is delicious precisely because it is so vindictive. In some places, the lyrics read like a bitter screed passed in the cafeteria from a hurt little schoolboy to the girl that left him blue: “You see me on the street / You always act surprised / You say, ‘How are you?’ ‘Good luck’ / But you don’t mean it.” Like blogger Tony Ling, I fully realize that this song “appeals entirely to [our] baser instincts,” but I “find Dylan’s directness bracing… it’s kind of nice to get a song that dispenses with the [experimental] Tarantula shit and just gets nasty.”

“Positively 4th Street” is often seen as a “little brother” to “Like a Rolling Stone” – Andy Gill even described it as “the second wind of a one-sided argument.” It was the next single Dylan released that year and directly preceded “Rolling Stone” in many of his concert sets. As Ling adds, “the songs have quite a bit in common – the arrangements both prominently feature signature organ lines, and the lyrics are a harsh indictment of somebody.” And yet “Positively 4th Street” is less narrative and even more confrontational. More than its predecessor, it leaves us wondering: who exactly was Dylan so pissed off at? Some commentators have suggested a specific ex-love interest, critic, or fellow music business professional as the song’s primary target, but most instead assume it represents a scurrilous attack on his old Greenwich Village folk crowd – after all, 4th Street is in the heart of the neighborhood. As Heylin explains, it “sure sounds like the product of a post-Newport Dylan, mightily pissed off for the second year running by those shouting, ‘Which Side Are You On?’ This time it is clear the gloves are off.” And yet for a song brimming with such unresolved hatred and self-righteousness, it sure is catchy!

35.) “Highway 61 Revisited” (1965)

God say, “You can do what you want Abe, but
The next time you see me comin’ you better run”
Well Abe says, “Where do you want this killin’ done?”
God says, “Out on Highway 61”

In its 2012 ranking of “The 500 Greatest Albums of All Time,” Rolling Stone listed Highway 61 Revisited at number four, describing it as “one of those albums that changed everything.” Named for the legendary “blues highway” stretching from Dylan’s home state to the Mississippi Delta, this title track is perhaps the wildest and most freewheelin’ on the album, setting the tone with a poetic punch and “raucous boogie blues” that still rocks your socks off. Out on Highway 61, it’s quickly apparent that we’ve again stepped into one of Bob’s troubled fever dreams, as unsettling as any surrealist landscape on the album. From the get-go, Dylan “is ready to roust another herd of sacred cows,” as Heylin puts it, subversively reworking the Biblical tale in which God commands Abraham to kill his son Isaac. By the end of Abe’s tête-à-tête with Dylan’s mob-boss deity, it’s clear that we “have entered a world where one cannot even rely on God to be good… [As Bob put it] that May, ‘I have no faith in a better world coming. I live now in this world.’”

The rest of the song continues in much the same vein, as Dylan leads us through four more disturbing vignettes involving a host of shady characters and culminating in a plot between a “rovin’ gambler” and a promoter to try and “create a next world war.” All of their questionable activities draw the characters out onto this lawless Mad-Max-like highway, which in Dylan’s imagining seems to have morphed into an apocalyptic representation of the dark side of American life. By song’s end, it feels like civilization is hanging by thread, if it’s not an outright mirage, again suggesting Dylan’s profound sense of dislocation and alienation within American culture at the time he wrote the album. “Counterculture” indeed. And yet, in spite of all this dark stuff, the song still seems as humorous as it is ominous. As Heylin concludes, “all one can do is grimace – or grin… Emphasizing the idea that the song is something of a hoot is the spontaneous inclusion of a kid’s toy police siren” unleashed numerous times throughout the tune. So even if he was in “frizzed-out jeremiad mode,” at least Dylan seemed to be having a good time.

36.) “Just Like Tom Thumb’s Blues” (1965)

I cannot move
My fingers are all in a knot
I don’t have the strength
To get up and take another shot
And my best friend, my doctor
Won’t even say what it is I’ve got

By “Just Like Tom Thumb’s Blues,” which followed the title track on Highway 61 Revisited, Dylan seems to be beginning to explore the downside to his manic, chemically-fueled ascent into the rock stratosphere during this year of astonishing creativity. There’s a loneliness and mournfulness here that is absent from earlier tracks on the album, a quality accentuated on Nina Simone’s stunning 1969 piano rendition – my favorite among numerous covers. The song’s lyrics seem to convey the after-effects of a bad trip or an epic binge, if not a kind of depressive episode. Dylan opens with one of his evocative vignettes: “When you’re lost in the rain in Juarez / And it’s Eastertime too / And your gravity fails / And negativity don’t pull you through…” In the “travelogue of mental and physical disarray” that follows, the narrator describes a series of harrowing experiences in the Mexican border town, which, as Rolling Stone explains, in his telling is “a dangerous, yet alluring, place… rife with drugs, corruption and ‘hungry women.’” Of course, there’s no evidence that Dylan himself had ever traveled to Juarez, but whatever he was getting at, it’s clear that his narrator feels profoundly out-of-sync with the dangerous, disappointing world in the song, not having nearly as much fun dealing with it all as he appears to on other songs from the period. In the final lonesome verse, he laments that “Everybody said they’d stand behind me… / But the joke was on me / There was nobody even there to call my bluff,” and at last decides he’s “had enough” and is heading home to New York.

37.) “Visions of Johanna” (1965)

Ain’t it just like the night to play tricks when you’re trying to be so quiet?
We sit here stranded, though we’re all doin’ out best to deny it

For the longest time, I didn’t understand why this song is unanimously considered one of the five best songs Dylan ever wrote. It’s not nearly as much fun to listen to as songs like “Tangled Up in Blue” or “Like a Rolling Stone” and the lyrics are dense and hard to purse out with a few superficial listens. But holy cow, once you dig down a bit you realize that this is some pretty incredible poetry. It’s like a great novel that’s a bit of a slog but sticks with you long after lesser works have faded. For starters, “Visions of Johanna” contains way more than its fair share of evocative lines – my favorites include the opening couplet (above) or these from the final verse: “The peddler now speaks to the countess who’s pretending to care for him / Sayin’, ‘Name me someone that’s not a parasite and I’ll go out and say a prayer for him.’” The lyrics also exhibit an almost “cinematic attention to detail,” with precise images like “In this room the heat pipes just cough” or “We can hear the night watchman click his flashlight.” Few Dylan songs establish so deep a sense of place as this one – you can almost inhabit the context in which it was written. 

Of course, the obvious question is, what on earth is Bob actually on about? By most accounts, he wrote the song as a kind of elegy for an ex- or idealized lover while living in New York’s Chelsea Hotel with his pregnant new wife Sara – possibly during a blackout, possibly on their honeymoon. Given the context, it seems like a rather strange thing to write about. As Daniel Durchholz explains, “At its most basic, the song contrasts two women: ‘Louise,’ who is nothing special, apparently, but is available (‘Louise, she’s all right, she’s just near,’ Dylan sings), and Johanna, who represents some kind of unattainable perfection – of love or art or…something.”

Most commentators assume that Louise is essentially a stand-in for Sara, while Johanna is more a personification of Dylan’s “longing for an absent ideal. Johanna may not even be real. But she is an addiction.” On the surface, this “addiction” may stem from a kind of erotic longing, but at deeper level it is likely aesthetic and spiritual more than anything. As Heylin explains, given how Dylan had struggled to write in the four months following the release of Highway 61 Revisited, “it is awfully tempting to see Johanna as his muse, who at the start of the song is ‘not here,’ but by the final line is ‘all that remain[s].’” By the release of Blonde on Blonde the following summer, it was clear Dylan had been given a few more such generous visits. But the concept of a muse is not only relevant to the creation of art, it’s a broader sort of spirit that animates human life, that gives us meaning and purpose. And this is the sense in which I find “Visions” to be so compelling. Dylan is playing a kind of “Waiting for Godot” character, forever engaged in the search for the ethereal, while also having to, like all of us, at times settle for the attainable, finding pleasure in the more routine and mundane aspects of life. There is a kind of “god-shaped hole” that pervades “Visions of Johanna.” Perhaps, just perhaps, it’s not a mistake that the name “Johanna” means “God’s grace.” As Schlansky explains, this “is a song that captures the feeling of being pushed to the edge of an emotional brink. It’s 4 AM in your soul, ‘last call’ at the bar of salvation, and you’re in the mood for one more drink.”

38.) “Stuck Inside of Mobile with the Memphis Blues Again” (1966)

Now the preacher looked so baffled
When I asked him why he dressed
With twenty pounds of headlines
Stapled to his chest

Folks sometimes look at Bob as he’s been in recent years – grumpy, decrepit, socially distant – and wonder, when did he get so weird? But there’s plenty from his magnificent mid-60s period to remind us that he’s always been a bit like that. It’s what has made his music interesting: if Dylan hadn’t been so obstinately independent all these years, he never would have felt the freedom to keep trying things that were unconventional, ever at the risk of being off-putting.

This is another one of those songs from the Electric Trilogy that is just delightfully weird – I mean, what else can you say about lines like “he just smoked my eyelids / An’ punched my cigarette”? The lyrics are again made up of surrealistic vignettes depicting the seemingly suspect activities of a madcap cast of characters – among them, a back-alley Shakespeare speaking “to some French girl,” an armed senator “Handing out free tickets / To the wedding of his son,” and a wild-eyed preacher with “twenty pounds of headlines / Stapled to his chest.” But even more than usual, it’s hard to make heads or tails of all this. I’m sure some experts might claim to have cracked the code, but in my mind the song just exhibits more of the “muddied consciousness” and “glorious insanity” you see in other Dylan works from the period. As Jason Rhode writes, “The lyrics prowl around into Dali-esque hinterlands only to return with the yowling lament… to conclude each stanza” – “Oh, mama,” Bob moans, “can this really be the end?”

Indeed, this bizarre seven-minute epic could be read as a portrait of his deteriorating mental health at the time and perhaps even an obscured cry of help from an increasingly alienated icon at the center of a white-hot cultural firestorm. Dylan wrote it in early 1966 at a time when the drugs, fast livin’, and public antagonism were clearly beginning to take a toll. He was discovering that there was a cost to maintaining this lifestyle – and that defiant artistic independence. As Tony Ling explains, “Phrases like ‘spinning out of control’ and ‘he doesn’t want you to see him this way’ pop up in… [biographers’] retelling of this period… One can only imagine the psychic blows he took every night in 1966, high as a kite and being booed for making incredible music.” Of course, this song preceded the notorious 1966 World Tour, but many of these conditions were already in place. As Ling concludes, “at the core the song is summed up by one line – ‘deep inside my heart / I know I can’t escape’… Dylan’s narrator can only bemoan his fate, stuck in the same kind of purgatory found in ‘Visions of Johanna.’” To me, that’s a great synopsis: Bob’s in a kind of purgatory here, trapped in a place that seems all wrong, and through the fog he can’t see a way out. Perhaps Bob’s message to the apocalyptic street preacher is also his bleak message to the rest of us, true or not: “‘You see, you’re just like me / I hope you’re satisfied’ /… stuck inside of Mobile / With the Memphis blues again.”

39.) “Just Like a Woman” (1966)

Nobody has to guess
That Baby can’t be blessed
Till she sees finally that she’s like all the rest

A 1971 New York Times article charged that there was “no more complete catalogue of sexist slurs than Dylan’s ‘Just Like a Woman,’ in which he defines woman’s natural traits as greed, hypocrisy, whining, and hysteria.” But I think that’s a stretch. There’s no doubt that Bob’s been guilty of some misogynistic lyrics – he’s said all kinds of demeaning things in song about the women in his life, and not just during his freewheelin’ mid-60s phase when he seemed to be spitting venom in every direction. But I don’t read this as a general “screed against womanhood” so much as a song about the exhaustion of dealing with a specific person, at times childlike and needy, who “hasn’t managed to grow up yet and, from the narrator’s perspective, probably never will… a song about the pain of love gone wrong.” Many of Dylan’s classic “kiss-off” songs can be read like this, which, even if perhaps that’s a tad disingenuous, makes them both easier to enjoy and more relatable. There’s no doubt that this is a “devastating character assassination,” but that doesn’t make it some kind of summation of Dylan’s feelings towards women.

Thomas Merton once wrote that “the love that unites us will bring us suffering by our very contact with one another, because this love is the resetting of a Body of Broken Bones.” Whether she’s supposed to represent Edie Sedgwick or “some similar debutante,” it’s clear that Dylan’s been wounded by this woman, and that’s what I hear when he sings of a lover who “breaks just like a little girl.” The music sounds sweet, but there’s no sweetness here: it’s a song full of the bitterness that comes from having had some very particular painful experiences. But it’s also pervaded by a sadness and desire that speak to his conflicted emotions. As he says, “It was raining from the first / And I was dying there of thirst / So I came in here / And your long-time curse hurts / But what’s worse / Is this pain in here / I can’t stay in here.” Bob knows he’s got to quit this woman, but it’s still complicated. As Rolling Stone writes, the song “is a complex portrait of adoration and disappointment, written as vengeance but sung as regret. Dylan never revealed a specific inspiration… But the song is more about his own turbulent lessons in romance – the giving, taking and leaving… ‘There’s a lifetime of listening in these details.’”

For all the issues some folks have with these lyrics, they still resonate with me. When I hear that chorus, for instance, I don’t necessarily think of my wife or sister or mother. I often think of all those times – too many to count – when I’ve been the one that acted like a pathetic child, when my emotions got the better of me and that unstable little brat inside showed up and picked a fight with the world just to defend my precious little ego. Whether or not Dylan would have admitted it when he wrote this in March 1966, I’d say we’re all pretty hard to live with.

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