Henry James. Virginia Woolf. James Joyce. Robert Frost. Zora Neale Hurston. James Baldwin. John Updike. Philip Roth. These towering authors were never awarded the Nobel Prize in Literature before they died.

In 2016, Bob Dylan, a troubadour by trade, who penned a single novel (the much-maligned Tarantula), was the first American to win the prize, 23 years after Toni Morrison. The Nobel committee’s spokesperson said that Dylan “created new poetic expressions within the great American song tradition.” True enough. But this bit rang hollow: “He can be read and should be read, and is a great poet in the English tradition.”

Few people, beyond a cadre of self-described Dylanologists, simply “read” Bob Dylan on the page, and study his work like a holy text. Reading the words apart from the music is a different, lesser experience – in the same way a great translation of Homer is still merely an approximation of an ancient, aural experience. There’s no audio recording of The Iliad or The Odyssey. But there are myriad examples of Dylan’s greatness laid down on tape: official and unofficial, studio cuts and outtakes, live snapshots and reboots, random flotsam and jetsam.

Bob Dylan isn’t Homer – or even a Joyce, Woolf or Baldwin – but he’s a particular kind of pop genius with no counterpart. We often lump him with the Beatles and the Stones. But those two bands peaked in the Sixties, while Dylan continues to ride the wavelength of decades-long summits and valleys, releasing some of his finest output long after his contemporaries have settled into greatest-hits complacency.

This project is a celebration of Bob Dylan and his brilliance across the decades. Not just his words alone, but the music too. Both are inseparable, hand in glove. We’re hailing Dylan’s best songs from each decade since he began recording.

The ‘60s marked his first apex, from the folk era to his “thin, wild mercury sound” to his post-motorcycle-crash embrace of country. Though nothing quite matches the richness of his earliest output, Dylan’s career is deep and wide. Further virtuosity arrived in the ‘70s, ‘80s, ‘90s and beyond. And we’ll get to that.

One programming note: You’ll notice the Basement Tapes tracks don’t appear in this first list, though technically recorded in the ‘60s. We argued back and forth and decided, since final touches were added to the music prior to the album’s official release, they fall squarely in the seventies. Otherwise, the date of recording counts. So: “Blind Willie McTell”, for example, is grouped with Infidels (1983), even though the song wasn’t officially released until 1991.

Now, let’s head back to Greenwich Village, 1962, where a young Minnesotan first found his voice. – Peter Tabakis

“Blowin’ in the Wind” (1963)

Bob Dylan has never been especially forthcoming about his work. Upon publishing “Blowin’ in the Wind” in a 1962 issue of the folk music magazine Sing Out!, Dylan didn’t offer much in the way of explanation: “There ain’t too much I can say about this song except that the answer is blowing in the wind,” he said. “It ain’t in no book or movie or TV show or discussion group […] too many of these hip people are telling me where the answer is but oh I won’t believe that.” Sixteen years later, Dylan shed some light on its origins, claiming it was inspired by the African-American folk song “No More Auction Block.” “‘Blowin’ in the Wind’ has always been a spiritual,” he said.

Reflecting on it in 2020, “Blowin’ in the Wind” sounds a bit antiquated—after all, you’re quite unlikely to hear it at a protest—yet disquietingly timely. Listeners who saw the song as a civil rights anthem would be dismayed to see that there are still protests in the streets, demanding freedom for not just Black Americans but queer Americans as well, and that there are still men who turn their heads and pretend not to see injustice and oppression. Sure, a lyric like, “How many seas must a white dove sail/ Before she sleeps in the sand?” sounds corny now, but consider how the cannonballs Dylan refers to in the very next line haven’t been banned so much as replaced by drones and rubber bullets. We’re still asking the same questions that Dylan asked nearly 60 years ago, and the answers are still blowin’ in the wind—elusive and enigmatic. – Jacob Nierenberg

“A Hard Rain’s a-Gonna Fall” (1963)

Before he was the “spokesman of a generation,” Bob Dylan was another Woody Guthrie wannabe knocking around Greenwich Village. He paid tribute to the man on “Song to Woody,” on which he warned of “a funny ol’ world that’s a-comin’ along […] It looks like it’s a-dyin’ an’ it’s hardly been born.” His vision of that world was never clearer, nor more ruinous, than it was on “A Hard Rain’s a-Gonna Fall,” the centerpiece of The Freewheelin’ Bob Dylan. Even more than “Blowin’ in the Wind,” “A Hard Rain’s a-Gonna Fall” set Dylan apart from the pack of Guthrie disciples, marking the moment Dylan went beyond emulating his hero and became something else.

The specters of death and destruction loom over some of The Freewheelin’ Bob Dylan’s best songs—“Masters of War,” “Talkin’ World War III Blues”—and on “A Hard Rain’s a-Gonna Fall” they loom so large as to blot out almost all light from the sun. Every new line that Dylan sings reveals a new horror—barren forests and oceans, a baby thrown to the wolves, 10,000 people who can neither speak nor listen—and it sounds as if the worst is yet to come. (He has said that each of those lines could have been the start of another, unwritten song.) All of the song’s tension is conveyed and built through Dylan’s words; there is no musical climax, just scene after scene in Dylan’s vision of the apocalypse. It ends with neither a bang nor a whimper, but a vow that Dylan will keep telling and thinking and speaking and breathing and singing his song until the hard rain washes everything away. The hard rain’s still falling, and Dylan’s still singing. – Jacob Nierenberg

“Don’t Think Twice, It’s All Right” (1963)

Clearly, it’s not all right. Dylan tries to make both himself and his ex feel better, but it doesn’t work for either of them or us. He casually explains that there’s nothing left to talk about, that their love never really flowered anyway and that it’s just time to move on. He never can quite convince himself, though. He works too hard to explain that there never really was a there there, all while longing for what could have been as he makes his middle-of-the-night escape. Part of him wants to linger, wishing she would say or do something, anything, to draw him back. He’s gone too far, though, and now he’s on the run.

Think about the words all you want, but give a second thought to the music. The finger-picked acoustic pattern moves energetically, but gently. It’s a neat little bit that hides its complex movement in its easy sound. That steady pulse becomes essential to the song. Dylan’s emotions jump and crash. It’s all okay, though, the music says more than the words. He can blame her, he can deny what was, he can get angry or bitter or hurt or anything, and that guitar part just keeps bouncing along. When he sings, “‘Goodbye’ is too good a word, babe,” we could take it three or four different ways. The guitar stays steady.

The song sounds so even-keeled, and, ostensibly, it’s a singer’s collected attempt to collect himself. The surface narrative works that way: a man recognizes the failure of an incomplete relationship, so he leaves amicably, wishing no ill-will toward his former partner. The subtext roils; he can’t quite convince himself; he can’t quite not blame her. Dylan take us into the midst of that, all while making the turmoil sound so pretty. – Justin Cober-Lake

The Lonesome Death of Hattie Carroll (1964)

More than any song in Dylan’s oeuvre, with the exception of “Hurricane,” “The Lonesome Death of Hattie Carroll” taps into the righteous anger fueling today’s Black Lives Matter movement. Based on a 1963 murder, Dylan confronted racism present in America head-on in what is one of his most-loved songs.

During the late hours of February 9, 1963, William Devereux Zantzinger, an heir to wealthy tobacco plantation, got extremely drunk at a ball in Baltimore and attacked the staff with a cane while spewing racial epithets. He struck barmaid Carroll on the head and she collapsed shortly after. She died eight hours later from a brain hemorrhage. Zantzinger was charged with murder and used drunkenness as his defense. The judge reduced his sentence to manslaughter and sentenced Zantzinger to a fine of $500 and six months in jail.

After reading about the case, Dylan wrote a protest song that immortalized Zantzinger’s wicked deeds. Though he misspelled his antagonist’s name and got the charge wrong, Dylan provides the listener a fairly comprehensive account of how Zantzinger killed Carroll. He also turns the blame on us in the classic refrain: “But you who philosophize disgrace and criticize all fears/ Take the rag away from your face/ Now ain’t the time for your tears.

The fact that Zantzinger’s wealth, race and social standing influenced the judges is not lost on Dylan. This message is particularly meaningful in an epoch where white Americans can protest while carrying weapons but a black American is murdered by the police for passing counterfeit money. Not much has changed since 1963, at least not enough to keep songs like “The Lonesome Death of Hattie Carroll” from being ancient history. And as for Zantzinger? He passed away in 2009 at the age of 69, holding firm that song was a total lie and that Dylan was a “no-account sonofabitch” and a “scum bag.” Spoken like a true, gentleman. – David Harris

“It Ain’t Me Babe” (1964)

Arriving on the cusp of an era of saccharine pop filled with false platitudes espousing the joys of young (male) love, “It Ain’t Me Babe” presents a far more adult read of the realities of relationships. “I’m not the one you want, babe / I’m not the one you need,” he sings, a direct contrast to the more optimistic paeans dominating the radio by the likes of the Beatles – a group to whom he provides a somewhat direct response to their positive “yeah yeahs yeah”s with the chorus’ “no no no,” In this, Dylan trusts his listeners to be of a more mature mindset, being able to look past the so-called puppy love of songs like “She Loves You” in favor of a more mature, even realistic portrayal of someone realizing that the object of one’s affection does not harbor any of the requisite traits that would lead to a fairy tale ending.

You say you’re looking for someone,” he rebukes the potential suitor at the start of the song’s three choruses, before launching into the very specific reasons he simply cannot make himself out to be that person: there will be no holding of doors, there will be no sacrificial love, no flowers nor heeding a constant beckon call. In this, Dylan presents himself as the archetypal rebel, one who chooses to stand outside the perceived and acceptable norms of society in favor of a life lived honestly and on his own terms. For a pop song, this is some seriously deep subject matter, showing Dylan to be light-years ahead of his soon-to-be contemporaries as he edged ever closer to a more pop and rock-oriented sound. It’s not for nothing that the Turtles selected “It Ain’t Me Babe” as not only their first single but the title of their debut album; it’s a song that’s as much of a statement as it is a deceptively hooky early folk rock number. – John Paul

“Subterranean Homesick Blues” (1965)

Given Dylan’s bohemian roots, it’s understandable that many see in “Subterranean Homesick Blues” a musical approximate of the Beats’ poetic ethos. To be sure, there is certainly a Kerouac/Ginsberg/Ferlinghetti/et al. influence running through the heart of the song – the title itself is an allusion to Kerouac’s 1958 novella, The Subterraneans, but anyone listening to “Subterranean Homesick Blues” within the context of the era will hear the clear Chuck Berry influence. Often hailed as rock and roll’s greatest poet, Berry’s fingerprints are all over the track, from Dylan’s hipster imagery to the song’s galloping rock-n-roll rhythm and lyrical cadence. “Too Much Monkey Business” is often touted as the song’s most direct influence given the mile-a-minute lyrical recitation, but you can hear traces of “Maybellene” and “Reelin’ and Rockin’” in the band’s arrangement and Dylan’s proto-rap.

Because of this, “Subterranean Homesick Blues” can easily and understandably be seen as Dylan’s first foray into the pop charts, having reached the Top 40 in the US and Top 10 in the UK. This, perhaps more than any other moment in Dylan’s post-folk phase of his career, marks the point at which he officially embraced rock ‘n’ roll, cribbing from its greatest artist to help forge his own electric identity. In essence, he co-opted Berry’s approach and recast the instrumental component within a white, hip New York aesthetic that would come as a natural extension of the Greenwich Village folkie he had originally posited himself to be before the arrival of the Beatles and the surge in the teen pop market. Acknowledging the past, Dylan here helps write the future of rock ‘n’ roll for the remainder of the decade. Of course, it doesn’t hurt that it carried with it one of the first examples of what would become the dominant musical art form in the coming decades, the music video, courtesy of the iconic promotional clip featured in D.A. Pennebaker’s seminal Dylan doc, Dont Look Back. Taken together, “Subterranean Homesick Blues” can be seen as a clear demarcation point between what was and what would be. – John Paul

“Maggie’s Farm” (1965)

Another Side of Bob Dylan might have presaged the move in some ways, but Bringing It All Back Home most noticeably marked Dylan’s transition from folk singer to rock ‘n’ roll star, with the record even divided into an electric and an acoustic side. “Maggie’s Farm” epitomizes the era perfectly. Throughout the track, Dylan rejects the power of dominant culture without acceding to the demands of the counterculture. Heard from one perspective, the song rages against mainstream politics and industry; read from another, it resists catering to the folk scene, the protest-song factory. “They say, ‘Sing while you slave,’ and I just get bored,” carries this tension further. Dylan snarls at people who want to use him for their own purposes, whether by writing the songs they want to hear or by happily singing while supporting the status quo. Dylan rejects all of it, attempting to opt out of everything (while, of course, making a hit record for a major label).

The song’s ambiguity lets it work as a general anthem of resistance, but Dylan’s details prevent it from becoming too vague to be effective. Allegorical readings quickly veer into incoherence (take a guess at who Pa is, for example, and then try to make the rest of it make good sense), but the song can still focus concerns about material production, hegemony, hypocrisy and related topics. With or without the context of Dylan’s biography, the track perfectly blends the personal and the political. You can feel oppressed by the system or by a particular jerk; you can fight capitalism or just your dead-end job. “Maggie’s Farm” responds to all of it, and it does so with humor and, of course, a trenchant argument from the guitar. – Justin Cober-Lake

“Love Minus Zero/No Limit” (1965)

“Love Minus Zero/No Limit” is a love song, but anything but simple. A paean to a lover who helps center Dylan in his chaotic world, “Love Minus Zero/No Limit” is one of the musician’s most oft-covered selections.

Lyrically, Dylan paints his lover in strokes of opposites, claiming that she “speaks in silence,” and that she is both possessed of fire and ice. Whether this lover exists in flesh incarnate or in the form of a vaporous muse is unclear. “My love she laughs like the flowers/ Valentines can’t buy her,” Dylan claims at the end of the first verse.

After establishing the dichotomous elements of this lover, Dylan then spends the three remaining verses enumerating the hostile conditions of the world that batter him while he seeks refuge with this woman or muse. While Dylan passes through derelict dime stores and bus stations, confronted with the judgments of his fellow man, his lover offers this sage advice: “She knows there’s no success like failure/ And failure’s no success at all.”

Throughout the song, Dylan makes allusions to William Blake, the Book of Daniel and even Edgar Allan Poe. The lyrics themselves hew close to Blake’s poem “The Sick Rose” while the lyric “Statues made of matchsticks/ Crumble into one another” echoes Nebuchadnezzar’s foolish notion of building a statue that will eventually fall.

The title itself is often misinterpreted. It should be read as a fraction such as “Love Minus Zero over No Limit.” It means there is no end to the muse’s love for the narrator, that it’s utterly impossible for this love to fail. Though the song is sometimes overshadowed by its brethren on Bringing it All Back Home, “Love Minus Zero/No Limit” is one of Dylan’s most romantic, up there with “I Threw It All Away.” Like the best sonnets and poetry, Dylan’s love will live on for generations, immortalized in these lyrics that are still scrutinized and dissected so many years later. – David Harris

“Mr. Tambourine Man” (1965)

In February of 1964, Bob Dylan took a road trip with some friends down to New Orleans for Mardi Gras; that same spring, back in New York, he composed two of his most fantastical tunes. “Mr. Tambourine Man” was written around the same time as “Chimes of Freedom,” both of which reflect Dylan’s reading of Rimbaud, sporting lyrics rife with surreal imagery. “Mr. Tambourine Man” is a nostalgic, deeply melancholic ode. Although the speaker is open and evokes a kind of optimism, there’s an edge of desperation to it: “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.” Later on, he sings, “Let me forget about today/ Until tomorrow.” It’s the sound of lost innocence praying to be whole again. As such, it’s fitting that the song opens the acoustic back half of Bringing It All Back Home, formally looking back at Dylan’s folk past even as he was being pulled inexorably into the future. The Byrds cover is the one that hit number one, after swapping out Dylan’s 2/4 time signature for 4/4, changing the key, adding a jangly 12-string intro inspired by Bach that would prove influential to groups ranging from Simon & Garfunkel to R.E.M. and, sadly, cutting all but one of Dylan’s verses. In many ways, it became a different song – Dylan, when he heard their version, supposedly said, “Wow, man, you can even dance to that!” But there’s something about the ragged yearning of Dylan’s original hymn – to a god, the muse, the self or the past – that makes it timeless. With none of the trim and polish of The Byrds’ version, Dylan’s dreamlike paean to art, belief and the imagination stands out as one of his finest achievements. – Tyler Dunston

“It’s Alright Ma (I’m Only Bleeding)” (1965)

The folk scene of the 1960’s was arguably built around the protest song. Each of these artists, from luminaries like Dylan to the unknowns strumming acoustic guitars in Greenwich Village coffee shops, had in their repertoire a number of songs lamenting the state of the world and railing against the men in power who caused this strife through malice and negligence. So many of these songs are rooted in specifics, even a number of Dylan’s. But by the time he wrote “It’s Alright Ma (I’m Only Bleeding),” Dylan had seemingly exhausted his protest material, and the world was getting worse. So, in what is arguably his last protest song for quite some time, Dylan broadened his scope and took the whole world to task.

“It’s Alright Ma” has a palpable anger to it that doesn’t often appear in Dylan’s acoustic work from the same period. Furthermore, Dylan’s words seem to abandon any sense of reality at all. He couples ideas and images over a repeated guitar line that serves to emphasize the surreal nature of the song. Dylan’s grievances with society, which range from consumerism to religious fundamentalism and cover just about every aspect of American capitalism, flow out at an unrelenting pace. Tellingly, he only stops to recite variations on the title, indicating that he’s not only angry at the world, he’s exhausted with it. As much venom as there is in Dylan’s indictments, there’s also a weariness that comes with the knowledge that these problems probably aren’t going to be solved any time soon. Some would call it cynical, but it would be more accurate to describe it as an acknowledgment of the limits of individual power. Society often turns to individuals as savior figures, but Dylan posits that the most that a single person can do in the face of societal woes is rage at the unrelenting horror of it all. – Kevin Korber

“It’s All Over Now, Baby Blue” (1965)

Like so many of Bob Dylan’s early songs, “It’s All Over Now, Baby Blue” is open to all sorts of interpretations. Dylan’s lyrics allude to images and people in American history and folklore, but while songs like “The Times They Are A-Changin’” used this imagery to invoke a sea change in society, “Baby Blue” is clearly concerned with the personal over the political or social. As Dylan sings the title over each chorus, his voice is filled with a combination of sorrow and pity, as if the subject of his ire is too pathetic to deserve the sort of venomous kiss-off that he would go on to write and record a few months later. Still, the question remains: who is Baby Blue?

Dylan obsessives may all have their own idea of who “Baby Blue” is supposed to stand for, but the idea of such a beautiful song being a direct allegory for a single person in Dylan’s life is both boring and a little insulting of Dylan’s writing. To get a better sense of what Dylan’s going on about, one could just look at the context in which “Baby Blue” was released. It appears at the back end of Bringing It All Back Home, his first album with a live band and electric instruments, and Dylan knew that the album would court controversy among the folk scene that made him famous. On “Baby Blue,” Dylan appears to be talking to the very people who were willing to cut ties with him over going electric, and his sorrow could stem from his frustration at how his colleagues and friends refuse to understand what he’s doing. For Dylan in 1965, folk was becoming something of an anachronism, and he was ready to move on. “Baby Blue” is one last, beautiful plea to his fans and fellow artists to understand. – Kevin Korber

“Like a Rolling Stone” (1965)

Imagine you haven’t heard it 1,000 times. Imagine you’d never been subjected to the ad nauseum overanalysis of a rock song. Imagine you didn’t know who Bob Dylan is and you didn’t have all the relevant context about controversial live shows and secret organ players and six-minute radio singles and everything else. Step back from all the Dylanology and decide if “Like a Rolling Stone” holds up as a good song, and not simply an important one.

The snare hit and the organ provide the foundation, with the rest of the band weaving through the tune in the way that the best rock does, sounding as if everything’s about to come undone even as it builds into something stable. Dylan’s internal rhyme in the opening verse is staggering, his speech pattern sounding natural even as it brings an unexpectedly artful flow. The end rhyme on “kiddin’ you” sets up the unusual form, but it also leads to tension with the “laugh about” in the next line, as we see our main character upended before she does. From there Dylan piles images and thoughts into a giant heap of disdain, the weight and energy accumulating their own momentum that takes a studio full of top musicians to direct.

But also, forget that. There’s a reason you’ve heard it 1,000 times and you’ve seen lengthy articles and even books on this single track. Brilliant songs often miss their cultural moment; songs born straight from the zeitgeist quickly sound dated. Few songs – in ostensibly ignoring a wider milieu – use that time (in this case both the mid-’60s and Dylan’s artistic transition) as a spring for timelessness. “Like a Rolling Stone” carries the burden of mythology with it, but it overcomes potential fossilization to persistently earns its canonization anew. – Justin Cober-Lake

“Ballad of a Thin Man” (1965)

A threatening ostinato piano motif dominates “Ballad of a Thin Man.” It prowls, bounds, leaps and pounces like a majestic jungle feline on the hunt. And, similar to an ordinary house cat, it toys with its small prey. The quarry in question is “Mr. Jones,” one of the great unnamed recipients of a songwriter’s ire. Carly Simon took notes. So did Amy Winehouse.

Dylan had a target in mind when he wrote the song, but that target has shifted across time and interviews. Whenever we approach a Dylan song as a puzzle to be solved, we end up with a single jigsaw piece missing from the box. It’s the fundamental flaw in our approach. However frustrating, he always withholds a tidy outcome. The puzzle remains unsolvable.

“Ballad of a Thin Man” is an all-inclusive jeremiad, a wide net that gathers all who screamed at his shift from a “Voice of a Generation” (a moniker he’s always hated) to the visionary who tore through “Maggie’s Farm,” plugged in, at the Newport Folk Festival in ‘65. “Something is happening and you don’t know what it is,” is just a roundabout way of saying “fuck off.”

The song lopes in circles, with organ exclamations, guitar flourishes and that upright piano backbone. It’s a thrilling kiss-off, one among many in Dylan’s oeuvre (see “Like a Rolling Stone,” “Positively 4th Street”). Though it follows a strict 4/4 meter, “Ballad of a Thin Man” feels like a dastardly waltz. Dylan is in the commanding lead, and we’re following, almost unsuspectingly toward a mine field or off a cliff. We’re swept away, eager to get blown up or thrown into a chasm. Such is his unique genius, and on an album track no less. – Peter Tabakis

“Desolation Row” (1965)

In a 1966 Playboy interview, Nat Hentoff asked Bob Dylan what his first accomplishment would be if he were elected the next President. “I would immediately rewrite ‘The Star-Spangled Banner,’” he replied, “and little school children, instead of memorizing ‘America the Beautiful,’ would have to memorize ‘Desolation Row.’”

The practicality of kindergartners committing to mind a nearly 12-minute folk fantasia notwithstanding, his response is only slightly less ludicrous than most policy pronouncements from our current Commander in Chief. Glibness aside, there’s a kernel of sincerity and truth to Dylan’s answer.

“Desolation Row” is a Dadaist portrait of societal decay that foretold the tumult soon to come: the assassinations of Martin Luther King Jr. and Bobby Kennedy, Altamont, the Manson murders, Kent State, the Vietnam catastrophe. Inoculating young Gen-Xers against a turbulent future may not have been the worst proposal, given the 21st century in general and the last few months in particular.

The song stretches across the runtime of three standard pop tunes and features figures that are historical (Einstein and Nero), literary (Quasimodo, the Phantom of the Opera, Casanova, Cinderella), biblical (Cain, Abel, the Good Samaritan), and Shakespearean (Romeo and Ophelia). T.S. Eliot and Ezra Pound show up for a short brawl. New characters wander in to masturbate in the corner (the Blind Commissioner) or sniff drainpipes with a physicist (the Jealous Monk) or play the penny whistle while progress unravels (Dr. Filth and his nurse). Dylan is world-building, but the world he’s building isn’t aflame. It’s already turned to cinders.

Dylan seems emotionally removed from, what Greil Marcus once called, “the scrap heap of Western Civilization” that this composition so marvelously depicts verse after verse. Dylan is playing an observer over a simple and indelible southwestern guitar lick. But he’s also the messenger, with a voice that rings front and center in the mix, directly in the ear. The archangel taps our shoulders as we awake, groggy, after missing the Day of Judgment. “Desolation Row” beautifully recounts what we’ve lost in the interim – the past, the present, the future – while soundly asleep. – Peter Tabakis

“Positively 4th Street” (1965)

You’ve got a lot of nerve,” Dylan sings in the opening line of “Positively 4th Street.” An artist known for ambiguous subversion, this direct statement might shock the listener into unexpected humor. But Dylan is dead serious. To reverse a tired formulation, he might as well be saying “it’s not me, it’s you.” And it doesn’t matter who he’s singing about, either. A favorite pastime of Dylanologists, tracking down the supposed targets of Dylan’s most acidic diatribes misses the point entirely. Dylan’s meteoric rise left a trail blazing with betrayals both real and imagined – with bridges collapsing into ash over troubled waters. He was, undoubtedly, an asshole. He was, undoubtedly, jerked around by people who thought they were smarter than he was. Of course, there were haters and jealous losers wishing him good luck, but not meaning it. So the song is about “them,” but it’s about him, too, unintentionally or not. The first-person, in Dylan, is unstable like that.

“Positively 4th Street” is something of a sequel to “Like a Rolling Stone” – filled with the same accusatory self-righteousness, but stripped of any shred of poetic fancy. Released as a single directly after that more iconic tune, this one is its musical ghost. Dylan re-purposes a similar chord progression and calls upon the ironic, jaunty organ – again – to great effect. Someday, when the score is tallied, it may be recognized that Bob Dylan has written more great kiss-off songs than any other American songwriter, but he’s never topped the last couplet of this one: “Yes, I wish that for just one time you could stand inside my shoes/ You’d know what a drag it is to see you.” The organ solo of the outro plays like the last laugh. – Ian Maxton

“Visions of Johanna” (1966)

In November 1965, in Queenston, Ontario, just north of Niagara Falls, something went wrong with a safety relay for one of the transmission lines at the Sir Adam Beck Hydroelectric Power Station No. 2, and 30 million people across Ontario, Pennsylvania, New Hampshire, Vermont, Connecticut, Massachusetts, Rhode Island and New York lost power for about 13 hours. This blackout provided the material groundwork for the psychological landscape Dylan would explore in “Visions of Johanna,” a song that brandishes the influence of the French Symbolists as well as the Beats on Dylan’s work. “Ain’t it just like the night to play tricks when you’re trying to be so quiet?” he sings, his mutter turning into a yell mid-phrase. Andy Gill said the song has an “air of nocturnal suspension… full of whispering and muttering.” In a way, it calls to mind T.S. Eliot’s Prufrock: “Let us go, through certain half-deserted streets,/ The muttering retreats/ Of restless nights in one-night cheap hotels,” he writes, in a stop-and-start rhythm that prefigures Dylan’s vocal stylings, which were notoriously difficult for a band to follow. Perhaps that’s one of the reasons Dylan had so much difficulty getting “Visions of Johanna” just right. He and his New York backing band went through fourteen takes; according to Dylan, they kept trying to play a hard rock song, and he kept trying to slow them down. It wasn’t until he went to Nashville, away from the song’s beginnings, that things came together. Something happened at that session; the Blonde on Blonde recording is lightning in a bottle, the way the band stutters and lurches alongside Dylan’s inimitable phrasing, from Joe South’s pulsating bass to Al Kooper’s chimerical organ. “Visions of Johanna” struck the perfect marriage between Dylan’s poetry – he was at the height of his powers here – and a band that was firing on all cylinders. – Tyler Dunston

“I Want You” (1966)

The last song recorded for Blonde on Blonde and the album’s first single, released as an appetizer preceding the full meal, “I Want You” is one of Dylan’s great love songs. What makes it shine, with the “thin, wild mercury sound” he aimed for, is that its complex, colorful characters, which included an undertaker, an organ grinder, a kid in a “Chinese suit” (interpreted by some as a reference to the Rolling Stones Brian Jones) and the Queen of Spades, all battle for and ultimately lose out to a simple human drive.

Dylan’s champions may call his lyrics poetry, which is overselling it; if “I Want You” isn’t timeless verse, it’s effective theater. Listen to the hard consonants of the opening verse the “undertaker,” “saxophones” “cracked bells;” then check out the softer modifiers, “guilty,” “silver” and “washed-out horns.” Dylan invokes Shakespeare on the album’s following track, “Stuck Inside of Mobile with the Memphis Blues Again,” and here he demonstrates a Bard-like care for diction that feels the way it sounds; those hard k’s and x’s are the sardonic tsk-tsks of an agitated man, but the subject of his desire sweeps it all away with syllables that float as easy as pie: “I want you/ I want you/ I want you/ So bad,” the meaning driven by repetition and obsession more than sound.

Waxing rock poetry with Nashville session musicians, and Al Kooper on keys, his organ timbres vaguely suggesting the medieval or liturgical (and a little bit of the carnival), the laid-back shuffling arrangement sells this verbal tension as a perfect just-about-three-minute pop song. “I Want You” showcases the genius that goes into a simple love song, its very internal conflicts evoking a whole world of human frustration and emotion, and that’s what makes his particular genius so transcendent. — Pat Padua

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

He makes it seem so effortless – and on The Basement Tapes, maybe it was; but the sessions documented on the complete Cutting Edge sessions reveal that it took more than a dozen takes for this Blonde on Blonde high mark to reach anything close to its final form. How did he get there? Simplifying the music, all the better to let its unusual structure sing out.

The harmonica intro that opens the song wasn’t anywhere in earshot during the first group of takes, but to a large degree that’s what sets it in motion, and introducing the troubadour, as it were. That instrumental fanfare – the folk-blues-rock equivalent of trumpet blares? – is a prelude to the teller’s tale: “The ragman draws circles/ Up and down the block,” which makes you think Dylan’s immersing you in a period piece, and apparently he is: if “Shakespeare’s in the Alley…/ Speaking to some French girl/ Who says she knows me well,” well, Dylan himself is in Elizabethan England, on the outskirts of the Bard’s sphere of influence. It might be presumptuous to place himself so close to the literary canon, but what this suggests is that even if Dylan was the voice of his generation, what he’s singing about is timeless – and what he’s singing about, as the song’s title announces, is alienation, confusion, the default mode of the young that turns out to be the default mode for hundreds of years.

Dylan’s best lyrics could inspire a book-length treatise, but it would mean nothing if he didn’t deliver expert pop craft, and that’s part of the brilliance of “Stuck”: a thoroughly unconventional, wandering structure (circling like the ragman) of mysterious meaning, feeding an easy-going midtempo rock song that’s mesmerizing for its entire seven minutes. Dylan still keeps audiences challenged and on the edge of their seats, as with his nearly 20-minute quarantine JFK surprise, and this wasn’t the first of his extended reveries. But it may be the best. — Pat Padua

Sad-Eyed Lady of the Lowlands (1966)

Dylan once went so far as to call “Sad-Eyed Lady of the Lowlands” the best song he’d ever written. It’s hard to know if he still agrees with that assessment decades later, but he’s never played the track live. This rarified treatment of the song is maybe a testament to the mythic circumstances of its composition. On February 15, 1966 Dylan and his band went into the studio around 6 PM. The songwriter sat in a corner and started writing while the band did a whole lot of nothing. Hanging out, playing cards, probably drinking and sleeping on and off until, some hours later, Dylan came to them with the whole song, talked them through the basics and, at 4 AM, they all started playing. The single take they recorded makes up the last side of the second LP of Blonde on Blonde.

The song is a catalog of surreal and hyper-specific observations about the titular woman – Dylan’s wife, Sara, a fact he would confess on the track that bears her name on Desire – followed by questions that beg her incommensurability. And Dylan, the plaintive, devoted lover, begs to be accepted into the gates of her city. The song is biblical in its lyricism – think Song of Solomon or Ezekiel – and almost carnivalesque in sound. The combination is haunting, making for a work of art that comes from a place where time has no dominion. That is to say, it’s a love song.

Kenny Buttrey, the drummer, would recall later that the band didn’t know how long the song was going to be. That’s why the instrumentation peaks long before the track ends. Things went on so long the band started cracking up at each other. What else could they do? Imagine looking over after eight or nine minutes and seeing Dylan in a total fugue state, ascended to another plane, floating somewhere beyond you. All you could do is laugh at your inability to follow him and wait for the chorus to come around again. – Ian Maxton

“All Along the Watchtower” (1967)

Dylan’s greatest hits have been fodder for everybody from The Byrds to Sheryl Crow, and it’s hard not to think of this John Wesley Harding highlight without mentally cranking up Jimi Hendrix’s explosive vision. Dylan’s peer/rival/mentor Dave Van Ronk wrote in his memoir that Dylan at this point in his career “could get away with anything” and argued that “All Along the Watchtower” is “simply a mistake from the title on down: a watchtower isn’t a road or a wall, and you can’t go along it.”

Well sure, but such was Dylan’s gift that he could take something seemingly unintelligible and make it seem rich with portent; it sounds biblical (some have pointed out echoes with the Book of Isaiah), and it proves again how much of a literary figure Dylan can be at his peak; like Faulkner taking the almost impenetrable, subjective prose of The Sound and the Fury and making it mesmerizing, Dylan blends vaguely dreamlike images with a moody acoustic backup to sell something that sounds both ancient and modern, like an Old Testament prophet emerging in the 20th telling us something terribly important that we just don’t understand.

But Van Ronk was onto something; like a fortune teller crafting predictions vague enough yet suggestive enough to sound prescient, Dylan taps the culture’s (eternal) anxiety: “There’s too much confusion/ I can’t get no relief” (a sidelong glance at the Stones’ “Satisfaction?”). He has no answers, but encourages us that, despite those “Who feel that life is but a joke…/ This is not our fate/ So let us not talk falsely now.” Keep watching, and listening, and most of all, remain open to what the soothsayer says; the answer to your problems, complex and simple, is right there: music, art, the watchtower at the top of your frail body, the mind. Dylan is after no less than the meaning of life; of course we don’t understand it? Who does? But it’s catchy, isn’t it? — Pat Padua

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