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Bob Dylan’s Top 20 Songs

on March 30, 2017, 1:30am
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Top Songs is a feature in which we definitively handpick the very best songs in an artist or band’s catalog. Sounds simple, right? Oh, if only.

A short while ago, this would have been just another dumb ranking of songs. However, if you abide by the recent opinions of the Swedish Academy, Bob Dylan songs now rank as literature — poetry, to be precise. I’ve always loosely defined a poet as someone who sees the same things as the rest of us through eyes capable of detecting some hidden truth and then possesses the voice to speak that truth. It’s what Dylan sings of in “A Hard Rain’s a-Gonna Fall” — that concept of the artist as messenger: “reflect it from the mountain so all souls can see it.” So, I thought it fitting when Patti Smith performed the song at the Nobel ceremonies, not so much because the composition, to the layman, builds and bursts with imagery and feels like we think poetry ought to, but because it, more than a half-century ago, charged songwriters with the same artistic obligations as poets, painters, and novelists. I do believe the Swedish Academy deserves praise for acknowledging Dylan’s contributions to literature, but let’s not pretend that they’ve told us anything we didn’t already know for decades about Bob Dylan or the power of popular music.

As for this list, picking among Dylan’s vast body of work wasn’t as difficult as anticipated. One might beg an editor for five more songs, but that only begets another five and so on. Suffice it to say, every song here touches a nerve, scrapes away at some truth, or puts into words and arrangements something we might not otherwise be able to tap into on our own. From the beginning, Dylan’s drawn from tradition, old songs, and literature, sifting through other accounts and reconciling it with the world around him. In many ways, he is that poet, interpreting humanity and reflecting it back to us in all its beauty, ugliness, and cruelty. If strangers in the distant future want to learn about us, the real story, they could do far worse than picking up a few Dylan records. In the meantime, here are 20 Bob Dylan songs that only he — poet, songwriter, or trapeze artist — could have reflected from the mountain.

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20. “All Along the Watchtower”

John Wesley Harding (1967)

In all but songwriting credits and royalties, this song belongs to Jimi Hendrix. Fans who have witnessed Dylan close out countless sets on his Never Ending Tour with “All Along the Watchtower” can testify that the rolling thunder and howling winds summoned by his band owe far more to Hendrix’s version. However, the portentous power of the original found on John Wesley Harding — brought forth by little more than Dylan’s foreboding tone, a piercing harmonica, and an acoustic strum — shouldn’t be overlooked. Whether you turn to Isaiah and Revelation for biblical interpretation or just let the song’s minimalist narrative play out, Dylan displays his knack for putting the listener right in the thick of things. Have both man and beast been stirred by the impending apocalypse, or is a singer-songwriter at the height of his fame and powers and having just recovered from a motorcycle crash looking for a low-key escape out a side exit? Either way, “All Along the Watchtower” cautions the listener that the center cannot hold and warns that all concerned, jokers and thieves alike, should get while the getting’s good.

Blowin’ in the Wind: “‘There must be some way out of here’/ Said the joker to the thief/ ‘There’s too much confusion/ I can’t get no relief'”

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19. “It Ain’t Me Babe”

Another Side of Bob Dylan (1964)

Pop music owes at least a third of its cannon to men professing their love for women and outlining the perilous slings and arrows they would face in order to win that lady’s favor. In actuality, there are limits to our chivalry, compromises, and willingness to change in order to accommodate love. By 1964, Dylan, much to the consternation of some listeners, had already begun drifting away from protest music and turning inward for songwriting inspiration. “It Ain’t Me Babe”, the final cut on the sea changing Another Side of Bob Dylan, further irons out a theme that Dylan introduced on “Don’t Think Twice, It’s Alright”: the desire for love but on his own terms. Some have read Dylan’s professions as a commentary on blind patriotism, but really it’s just a brutally honest breakup song. Dylan’s attitudes towards women are surely worthy of a doctoral thesis statement and several subsequent volumes, but 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.

Blowin’ in the Wind: “Go lightly from the ledge, babe/ Go lightly on the ground/ I’m not the one you want, babe/ I’ll only let you down”

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18. “Cold Irons Bound”

Time Out of Mind (1997)

Not many artists are reborn at 55. By that time, a songwriter generally sticks to treading the terrain he staked out for himself long ago. But on Time Out of Mind, Dylan, who hadn’t released a record of new material in seven years, blew past old boundaries like a Depression-era bank robber racing for state lines. It’s an agitated, pining, and paranoid album, and nowhere do those emotions register more tangible than on “Cold Irons Bound”. Amid driving percussion and echoing dirt-road blues, Dylan fails to square a love and obsession that just can’t be reasoned with. This isn’t a tearful goodbye and gallop off into the sunset; this is a collision course that a desperate and broken man seems powerless to avoid. Like so much of Dylan’s turn-of-the-century work, there’s zero compromise to be found here. The wounds are deep, the pain is unbearable, and any possible consolation is blowing in the wind.

Blowin’ in the Wind: “One look at you and I’m out of control/ Like the universe has swallowed me whole”

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17. “Just Like a Woman”

Blonde on Blonde (1966)

“Nobody feels any pain/ Tonight as I stand inside the rain,” sings Dylan, amid pitter-patter percussion, in the opening lines of “Just Like a Woman”. Blonde on Blonde has no shortage of ambiguous love songs, finding Dylan steeped in pain but not quite laying all his cards on the table either. We know he’s been wounded badly by “baby,” but are the comparisons between “woman” and “girl” put-downs or acknowledgements of her own pain? I’m not sure that figuring out the answer to that question unlocks anything more in this song, just as determining whether or not the woman in question was actually Joan Baez or Edie Sedgwick probably doesn’t matter. While pop music had traditionally rendered love songs as black-and-white affairs, these trips into Dylan’s headspace always offer far more complicated scenarios, the type where we can simultaneously pine for someone and yet know going back would be emotional suicide. It makes those days of protest songs seem like child’s play by comparison, doesn’t it?

Blowin’ in the Wind: “When we meet again, introduced as friends/ Please don’t let on that you knew me when/ I was hungry, and it was your world”

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16. “The Lonesome Death of Hattie Carroll”

The Times They Are a-Changin’ (1964)

When asked where his songs come from, Dylan has had a wide variety of answers over the years. Sometimes, he’s likened the process to catching songs floating down a stream with a net; other times, he’s made it seem like a more mystical act of spiritual receptiveness; and still other times, he’s simply shrugged. The origins of “The Lonesome Death of Hattie Carroll” lack that sort of vague explanation. Dylan simply clipped the story out of the newspaper. Carroll was a 51-year-old black maid working for William Zantzinger, a member of a wealthy white farming family in Maryland. Dylan’s song captures an incident in which a drunken Zantzinger dealt Carroll a blow with his cane that would ultimately lead to her death soon after. At the end of each verse, Dylan urges against tears until the courts have made their ruling, which ultimately sentenced Zantzinger to a slap-on-the-wrist six months in a cushier county jail. Incidentally, the verdict came down on the same day that Martin Luther King, Jr. delivered his iconic “I Have a Dream” speech on the steps of the Lincoln Memorial. Now is the time for your tears, indeed.

Blowin’ in the Wind: “Ah, but you who philosophize disgrace and criticize all fears/ Bury the rag deep in your face/ For now’s the time for your tears”

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15. “Mr. Tambourine Man”

Bringing It All Back Home (1965)

Bob Dylan recorded all the material for Bringing It All Back Home, Highway 61 Revisited, and Blonde on Blonde in a 14-month period. Let that float around under your leopard-skin pill-box hat for a moment. Think of the evolution across those three albums that took place practically overnight. And consider how many zeitgeist-altering songs, including “Mr. Tambourine Man”, came into being in those few short months. (Talk about punctuated equilibrium!) Even relatively simple songs like this one, which Dylan wrote about intense exhaustion following a Mardi Gras celebration, have left indelible marks on popular music. If the whirling, dazzling phrasing of Dylan’s proposed adventure isn’t enough in his own words, then consider David Crosby’s, who had a No. 1 hit with the song as a member of The Byrds, claim that “Mr. Tambourine Man” all but introduced poetry to music radio. Simply put, for a few years there, Dylan was inventing or reinventing popular music as we know it with practically every song he wrote.

Blowin’ in the Wind: “Yes, to dance beneath the diamond sky/ With one hand waving free/ Silhouetted by the sea/ Circled by the circus sands/ With all memory of fate/ Driven deep beneath the waves/ Let me forget about today until tomorrow”

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14. “Hurricane”

Desire (1976)

“Pistol shots ring out in a barroom night…” It’s that vivid opening line, practically a stage direction, that immerses the listener in that hot, violent summer night of 1966. And it was the perceived injustice levied against boxer Rubin “Hurricane” Carter that led to Dylan stepping back into the ring as a protest songwriter. When Columbia worried that some of the creative license taken in the song’s lyrics (co-written by Jacques Levy) could lead to legal troubles, Dylan opted to re-record the track. The faster take with on-the-beat percussion and Scarlet Rivera’s tailing violin puts the listener out cruising the New Jersey streets as the getaway car peels out and sirens follow in hot pursuit. The song drew additional attention to Carter’s case, and many credit Dylan’s musical nudge as being one in a long series that eventually led to Carter’s release a decade later. The song remains not only one of Dylan’s most urgent protest compositions but also an example of how the once surrealist poet could plot out a narrative and breathe so much life and desperation into it.

Blowin’ in the Wind: “Now all the criminals in their coats and their ties/ Are free to drink martinis and watch the sun rise/ While Rubin sits like Buddha in a 10-foot cell/ An innocent man in a living hell”

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13. “Shelter from the Storm”

Blood on the Tracks (1975)

While the rest of us sob in our beer and whine in our wine, artists have the additional option of laying out the remnants of a shattered heart for all to see. Dylan’s Blood on the Tracks (what a title) tops most lists as the greatest breakup album of all time because of its brutal honesty, equal parts scathing, sweet, and decimated. And a track like “Shelter from the Storm” shows how all those disparate emotions can be felt at once. The song begins with a woman, the protagonist’s salvation and someone who makes him a better man, offering him that shelter and reprieve from the harshness of life. However, by song’s end, she’s gone, and her words (“Come in, I’ll give you shelter from the storm”) now only haunt the man, who has been cast back out like a creature into the wilderness. Talk about a bright note to end a record on.

Blowin’ in the Wind: “‘Twas in another lifetime, one of toil and blood/ When blackness was a virtue, the road was full of mud/ I came in from the wilderness a creature void of form/ ‘Come in,’ she said, ‘I’ll give you shelter from the storm'”

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12. “Positively 4th Street”

Non-Album Single (1965)

When I first heard “Positively 4th Street” on the radio as a kid, I almost thought of it as a put-on or endurance test. With its loopy, carefree organ, it sounded a bit like its predecessor, “Like a Rolling Stone”, but that damn sing-along chorus just never seemed to come. I couldn’t think of another song on radio at the time that didn’t have choruses. Even after I eventually gave up on a refrain, the warmth of the music masked for a couple more years that this was actually an open-letter put-down, the equivalent of a modern-day hip-hop diss track. So, who was Dylan pissed at? Some argue the song’s directed at the folk and Greenwich Village scenes he’d moved on from while others have speculated it could have been about a number of critics and individuals within the music business or even friend and Warhol girl Edie Sedgwick. Dylan’s lips are forever sealed on the matter, and “Positively 4th Street” continues to rank right up there alongside the great musical slams of all time. Oh, no he didn’t.

Blowin’ in the Wind: “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”

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11. “Boots of Spanish Leather”

The Times They Are a-Changin’ (1964)

The ballad “Boots of Spanish Leather” unfurls as a dialogue between two lovers, a woman setting sail for a trip overseas and a man remaining behind. The first six verses find her asking him what he might like her to send him as a souvenir, to which he continually insists that her safe return would be enough. Her suggestion that she might be gone for a long time, along with a letter she sends him, which he reads and replies to in the final three verses, makes it clear to him that their love is over and that the gift is at worst a sort of buy-out to ease her guilt and at best a token to remember her by. Dylan, not known for his narratives, brilliantly shows the unraveling of the relationship in verse, especially the final words the man sends, as seen below. We find his earlier poetic, romantic sentiments replaced by pleasantries and an order for one pair of Spanish boots. It’s a simple, yet heartbreaking tale showing Dylan as a master of a common folktale trope.

Blowin’ in the Wind: “So take heed, take heed of the western winds/ Take heed of the stormy weather/ And yes, there’s something you can send back to me/ Spanish boots of Spanish leather”

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10. “Things Have Changed”

Wonder Boys OST (2000)

Dylan seemed to have taken out a new lease on songwriting in the late ’90s, which resulted in the brilliantly dark and murky Time Out of Mind, so there really couldn’t have been a better time for Wonder Boys director Curtis Hanson to ask Dylan to contribute to his soundtrack. Still, Hanson couldn’t have possibly expected the gem Dylan sent him back in the mail a few weeks after they had met to discuss the project. “Things Have Changed” feels like a getaway car careening through the mind of the film’s protagonist, Grady Tripp; it’s restless, agitated, paranoid, boxed in, and scarily seductive. Not only did the song set the tone for the entire dark comedy, but Dylan found himself receiving an Oscar for his work at the following Academy Awards. In his acceptance speech, broadcast from Sydney, Dylan described “Things Have Changed” as as song that doesn’t “pussyfoot around nor turn a blind eye to human nature.” It’s a description that can be applied to the bulk of his work since.

Blowin’ in the Wind: “There’s a woman on my lap, and she’s drinking champagne/ Got white skin, got assassin’s eyes/ I’m looking up into the sapphire-tinted skies/ I’m well dressed, waiting on the last train”

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

Bringing It All Back Home (1965)

“I don’t know how I got to write those early songs,” Dylan told 60 Minutes’ Ed Bradley in 2004, before reciting the first verse of “It’s Alright Ma (I’m Only Bleeding)”. “Try to sit down and write something like that … there’s a magic to that, and it’s not Siegfried & Roy kinda magic.” Panning down a lyric sheet to the song, you do get a real sense that Dylan once had access to a type of inspiration that many of us never quite get to tap into. Mostly spoken, with a nested rhyme structure, “It’s Alright Ma” scans like a laundry list of critiques, maxims, and warnings, each section consummated by a less-than-comforting reassurance that things will be alright. It’s a hypnotic song that does sound like it could’ve only been written at a particular time and place by Dylan. While we try to be fair and accept that Dylan is merely a singer-songwriter and not all the unwanted labels people once heaped on him, this type of song continues to make it hard for many to simply accept his humility.

Blowin’ in the Wind: “From the fool’s gold mouthpiece/ The hollow horn plays wasted words/ Proves to warn/ That he not busy being born/ Is busy dying”

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08. “A Hard Rain’s a-Gonna Fall”

The Freewheelin’ Bob Dylan (1963)

Many critics and listeners have described “A Hard Rain’s a-Gonna Fall” as apocalyptic. That’s not unreasonable considering it appears on the same side of an LP as “Masters of War”, and the outcome Dylan wails about surely sounds like man’s comeuppance, be it nuclear fallout, a great flood, or some other demise. Other lines subtly or acutely depict a world of injustice and suffering that we still recognize today. For instance, while Dylan may have been referring to media lies when he sang about “pellets of poison … flooding the waters,” listen to that line today and try not to think about Flint, Michigan. Dylan’s point remains: Some are prospering, others are suffering, and we’re collectively marching towards the consequences of living in that type of cold and callous world. The song itself feels like that doomed march, and yet that last verse offers up the slightest glimmer of hope, as the “blue-eyed son” says he going to go back out among the suffering he witnessed and sound the warning siren until his last breath. Really, that blue-eyed son could be Dylan. A half century later, the question remains: Why haven’t we heeded the warning?

Blowin’ in the Wind: “And I’ll tell it and think it and speak it and breathe it/ And reflect it from the mountain so all souls can see it/ Then I’ll stand on the ocean until I start sinkin’/ But I’ll know my song well before I start singin'”

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07. “Masters of War”

The Freewheelin’ Bob Dylan (1963)

“I could just kill you for that,” Henry Fonda’s Juror #8 hams in 12 Angry Men, explaining how it’s a phrase we use all the time but never really mean. Well, when Bob Dylan sings, “I hope that you die/ And your death’ll come soon,” he means it, Hank. If “Positively 4th Street” saw Dylan taking shots at old scenes or acquaintances, “Masters of War” finds him putting the entire military-industrial complex on notice. Borrowing its arrangement from the traditional “Nottamun Town”, Dylan circles those who hide behind desks and in blood mansions like a vulture in this scathing polemic, until the final verse finds him promising: “I’ll stand over you grave/ ‘Til I’m sure that you’re dead.” Never does he relent or break stride, like a hunter methodically stalking his kill. While other protest songs on Freewheelin’ left room for ambiguity and hope, Dylan acts as victim, judge, jury, and undertaker here, leaving no room for the guilty to wiggle free. Half a century later, it’s still devastating (and necessary) to see “Masters of War” performed by Dylan or the many who cover the song.

Blowin’ in the Wind: “I think you will find/ When your death takes its toll/ All the money you made will never buy back your soul”

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06. “Desolation Row”

Highway 61 Revisited (1965)

It’s almost like Dylan knew he needed something hefty, something remarkable in its own right to close out Highway 61 Revisited and be the bookend paired with “Like a Rolling Stone”. The result is the sprawling, entropic marathon through “Desolation Row”, a parade not unlike Sherwood Anderson’s grotesques, only Dylan’s characters are mostly historical, biblical, or fictional. Of course, many have speculated about meaning, identities, and just where the “real” Desolation Row might exist, but all of that seems far too strenuous. It’s an ambitious folk ballad without narrative from which Dylan only occasionally surfaces for air or harmonica interlude. After hundreds of listens, its persistence, enchantment, and fascinatingly odd characters still draw me in with the clear understanding that this should only be a visit and never a permanent arrangement. If ever a song felt “literary,” however you choose to define that term, “Desolation Row” has ascended that peak.

Blowin’ in the Wind: “All except for Cain and Abel and the Hunchback of Notre Dame/ Everybody is making love or else expecting rain”

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05. “Tangled Up in Blue”

Blood on the Tracks (1975)

Dylan gets credit for a lot of things as a songwriter. He receives kudos for repurposing traditional arrangements, bringing the protest song into public consciousness, and setting surrealist poetry to electricity, but rarely does he get counted among the better storytelling songwriters out there. And then there’s “Tangled Up in Blue”, which somehow works, despite its abstract nature, looseness with time, and fickle narrative structure. In fact, it’s that wild abandon matched with Dylan’s sharp, dazzling lyrical work that make it something that breathes and feels natural, even as Dylan tinkered with it for a decade after recording it. Somehow, Dylan moves us from that fanciful waking thought in the opening verse (“Wond’ring if she’d changed at all/ If her hair was still red) to that desperate need to find her again (“So, now I’m going back again/ I got to get to her somehow”), and it’s a journey always worth getting tangled up in.

Blowin’ in the Wind: “Early one morning the sun was shining/ I was laying in bed/ Wond’ring if she’d changed at all/ If her hair was still red”

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04. “Blowin’ in the Wind”

The Freewheelin’ Bob Dylan (1963)

Although it didn’t appear until his second album, The Freewheelin’ Bob Dylan, most people’s relationship with the songwriter begins with “Blowin’ in the Wind”. Dylan claims to have written it in 10 minutes, and his spare strumming and steady delivery sound simple enough to have actually hitched a ride on the wind itself, but the song’s impact has been profound and lasting. For many, it introduced the modern idea of the protest song and became the anthem of the Civil Rights Movement in America. Upon first hearing the song, Mavis Staples recalls being shocked that a young white man could express the plight of African Americans so acutely. King of Soul Sam Cooke not only took to performing Dylan’s song but responded with his own anthem, “A Change Is Gonna Come”. And the song remains as relevant as ever as we sadly address many of the same questions Dylan posed more than half a century ago. However, the most important, and perhaps damning, question still remains: When Dylan assures us that the “answer is blowin’ in the wind,” does that mean it’s so simple that it’s staring us right in the face, or are we doomed to forever chase the solution like an elusive feather riding a relentless gust?

Blowin’ in the Wind: “The answer, my friend, is blowin’ in the wind/ The answer is blowin’ in the wind”

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03. “Visions of Johanna”

Blonde on Blonde (1966)

I could spend the rest of my life trying to explain what “Visions of Johanna” means to me. Suffice it to say, from the moment I first heard that drawn-out, whining harmonica and “skeleton keys in the rain” as part of the Royal Albert Hall bootleg, not Blonde on Blonde, I couldn’t be without it. I doubt I’m alone in that assertion, and I feel that way about many of the songs on this list. Dylan apparently wrote the song during a New York blackout, and many purport that “Louise” acts as a stand-in for Dylan’s eventual first wife, Sara, while the songwriter was still dating singer Joan Baez (“Johanna”). It may ultimately be a song, like countless others, about grass being greener elsewhere and pining all night long for the one you aren’t with, but Dylan turns that all-too-familiar feeling of missing someone into an epic that, for all we know, never leaves that emotionally detached room where “the heat pipes just cough.” It’s a song that can keep you speculating for a lifetime, but even a dumb teenager understands how the night often”plays tricks when you’re trying to be so quiet.” Dylan manages to turn our mundane hangups into anguish worthy of epic poetry.

Blowin’ in the Wind: “The ghost of electricity howls in the bones of her face/ But these visions of Johanna have not taken my place”

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02. “The Times They Are a-Changin'”

The Times They Are a-Changin’ (1964)

Great songs touch upon some truth, and that’s why they remain timeless. No matter how politics, technology, or society evolve, some ideas prove eternal for us. Dylan set out to create an anthem of change for his generation, and “The Times They Are a-Changin’” became much more than that. Not only do its general lyrics make it a timeless call to action, but it also speaks to ideas of inevitable justice and the need for each generation to understand both its purpose and duty to step down once that purpose has been served. To me, in that sense, it’s always been a baton song of sorts. One that asks you to play your part and then let others step in and play theirs, hopefully having eased that next generation’s path a bit. Not sure of this song’s relevance? Think of any social injustice that still plagues our society, and then consider all the “writers and critics,” the “senators and congressman,” and all the “mothers and fathers throughout the land” who don’t “lend a hand” but instead actively oppose positive change. As hatred, bigotry, and superstition continue to rear their ugly heads, we can only hope that humanity chooses to swim rather than sink like stones.

Blowin’ in the Wind: “The battle outside ragin’/ Will soon shake your windows and rattle your walls/ For the times they are a-changin'”

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01. “Like a Rolling Stone”

Highway 61 Revisited (1965)

Everything that can be said about “Like a Rolling Stone” has been written. All that’s left to do is continue embracing that euphoric opening kick, snarling alongside Dylan, and soaking in its electric poetry, glowing rebelliousness, and sneering polemic. Highlight it, underline it, and for god’s sake, make sure your kids have it on their playlists. We all have songs that shift the cargo in our hulls, so to speak, when we first hear them — songs that change how we listen and think. I’m not sure I entirely trust someone who isn’t stirred by Al Kooper’s cranked-up, improvised organ or holds up to Dylan’s “How does it feel?” line of questioning. Some things are simply universal, and that’s to be cherished. To this day, in any country that Dylan’s Never Ending Tour takes him to, audiences pump their fists and shout back that interrogative refrain as the band closes down its set. In a world that seems doomed by its differences, it’s hopeful to see that certain things translate across borders, oceans, and cultures with a direction that hits home.

Blowin’ in the Wind: “How does it feel?/ How does it feel?/ To be on your own, with no direction home/ Like a complete unknown, like a rolling stone”

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