By the summer of 1965, Bob Dylan wasn’t just restless; he was actively shedding skin.
Fame had arrived early and loudly, and he seemed determined to antagonize it before it could settle in. Bringing It All Back Home had already kicked a hole through the folk barricade, half electric, half daring anyone to accuse him of betrayal. Newport Folk Festival followed, amps turned up, boos cascading, Dylan looking less wounded than entertained.
The narrative hardened immediately: prophet, traitor, sellout, savior. Dylan responded by accelerating. Highway 61 Revisited didn’t arrive as a course correction. It arrived as a refusal. He was twenty-four, touring relentlessly, sleeping erratically, writing at a clip that suggested urgency rather than ambition, buzzing as fast as chemistry and momentum could take him. If the world wanted reassurance, Dylan offered friction. If people were waiting for guidance, he gave them better questions.
“Something is happening here, but you don’t know what it is. Do you, Mister Jones?”
This record sits squarely in the middle of one of the most improbable hot streaks in popular music: Bringing It All Back Home, Highway 61 Revisited, Blonde on Blonde. Albums released like volleys, barely letting the dust settle before the next one landed. Dylan wasn’t refining an argument. He was outrunning it. Folk purists wanted hymns. Rock audiences wanted heroes. Dylan sounded increasingly uninterested in either role. There’s a sneer baked into this album, but it isn’t contempt so much as impatience. The sound of someone who knows the times are a-changing and has no intention of slowing down so everyone can reach consensus.
The roots don’t disappear here; they get stressed until they misbehave. Folk taught Dylan lineage and portability, the idea that songs could move hand to hand, town to town. The blues taught him posture and compression, how repetition could sharpen rather than dull, how irony could carry truth without apology. The Beat poets gave him velocity and permission, lines long enough to breathe, images stacked without explanation. Gospel gave him cadence and weight. From his friend Mavis Staples, he absorbed something rarer: conviction without theater, belief that didn’t ask to be admired. The Beatles mattered too, not as lyricists but as accelerants, proof that strange ideas could travel fast if melody did the driving. Ray Davies showed him the power of observation, how characters could carry meaning while the songwriter stayed half a step back. All of it feeds into Highway 61 Revisited, an album that sounds less composed than cornered, language snapping because it refuses to behave.
That refusal didn’t stop with Dylan. Songs no longer had to obey inherited forms or resolve politely. They could bend themselves around truth, even if the frame warped. You hear it when Joni Mitchell lets harmony drift to match memory, songs unraveling like maps redrawn mid-journey, when Neil Young trusts the cracked edge of a take, knowing that after the Gold Rush there’s no point pretending polish tells the truth.
Patti Smith takes poetry out of the library and into the streetlight, Jesus dying for somebody’s sins but not hers, language snarling its way back to the body. You hear it when D’Angelo lets groove sag and breathe until soul music starts talking about the root of the matter, flesh and faith tangled together, rhythm moving slower than expectation but heavier than truth. You hear it when Kanye West turns songs into arguments with himself, form buckling under ego, doubt, and gospel, chasing a freedom he keeps insisting he finally feels while never quite sounding convinced. You hear it vividly in Kendrick Lamar, folding theology, rage, memory, and contradiction into rap without smoothing the seams, standing at the crossroads asking how much a dollar really costs, and in Frank Ocean, whose songs arrive half-formed, drift, disappear, trusting absence as much as presence, nights moving slow, thoughts breaking off mid-sentence.
Hovering above all of them is Tom Waits, who learned early that Dylan had already settled the matter. A song didn’t need to sound right to be right. It just needed nerve and the willingness to leave the lights on and let the wreckage show.
The album announces itself with “Like a Rolling Stone,” a song that doesn’t so much begin as confront. Six minutes of forward motion dismantling status, comfort, and certainty while sounding almost cheerful about it. Identity collapses, homes evaporate, and the listener is left exposed, asked how it feels without being offered shelter. “Tombstone Blues” follows at a sprint, images tumbling over one another, jokes landing sideways, authority figures wandering in only to be mocked out of the room. It’s blues logic pushed to absurdity, repetition as provocation. “Ballad of a Thin Man” sharpens the knife further. Confusion itself becomes the target. The song doesn’t explain the joke. It lets Mister Jones keep asking questions long after the room has moved on.
On the other side of the record, the scope widens and the smirk deepens. “Highway 61 Revisited” drags American mythology onto the roadside and treats it like a bad business deal. Sacred stories become transactions. Legends negotiate. Everyone sounds faintly ridiculous, which feels deliberate. And then there’s “Desolation Row,” which doesn’t conclude the album so much as abandon it. History, literature, cruelty, romance, all stacked together without hierarchy. Commerce and catastrophe share shelf space. No rescue arrives. No door opens to heaven. The song inventories the wreckage and wanders off, unconcerned with whether anyone followed.
The cover understands this posture perfectly. Dylan sits forward in a patterned shirt, hair doing whatever it wants, expression closed for business. He isn’t performing or provoking. He’s mocking the very expectation that he should. The room behind him stays plainly visible, the camera and its witness left in the frame like an unedited thought, a quiet reminder that the act of watching has already been absorbed into the performance. Nothing is softened. Nothing reaches for myth. This isn’t rebellion as costume. It’s transition as fact. Dylan looks like someone who has already tangled things up in blue, cinched the knots, and walked away without the slightest interest in straightening them out for anyone else.
When Highway 61 Revisited landed in 1965, it mattered because it refused comfort. America was splintering, authority wobbling, inherited assurances sounding thin. Dylan didn’t translate the chaos into slogans or promise that a hard rain would wash it clean. He let the confusion speak in its own broken tongue. That’s why the album still endures, still sharp, still dangerous. It doesn’t promise clarity. It promises recognition. Power still postures. Meaning still gets merchandised. People still ask which way the wind blows while standing directly in it.
This is late afternoon music for a solitary walk, the kind you take on a local trail like East Palisades, where the path pares everything down to breath, footfall, and whatever’s rattling around in your head. Best near the end of summer, when the heat finally breaks, and the river below looks older than your problems. Earbuds in, volume just loud enough to spar with whatever life is humming in the trees, moving forward with no destination to defend. Go alone. This album prefers it that way. It knows that not every road resolves, not every question gets answered, and not every door, no matter how familiar, is meant to open.
In the end, Highway 61 Revisited doesn’t instruct. It provokes. It sneers, shrugs, laughs, keeps going. Dylan isn’t offering a map. He’s testing endurance, yours and his. The road is open. The signs are strange. Something is happening here. Whether you recognize it or not has never really been the point.
Megan’s favorite song on this album is “Like a Rolling Stone”. There are few songs that can be added to any playlist, but this is one of them. It can be the soundtrack to your stroll through the city, your dinner party, a funeral, a wedding, you name it. It’s one of those tracks whose dying question, “how does it feel?”, begs to be screamed into mid-air. A first-of-its-kind diss track, “Like a Rolling Stone” depicts has-been Miss Lonely’s downfall — a demise that Dylan sounds pretty happy about, and a possible portrayal of a middle finger to the industry he was wrapped up in.
Fresh off of tour and burnt out, Dylan was toying with quitting music altogether, stating he was tired of being put in a box and felt uninspired. But rookie session player Al Kooper, who improvised the Hammond B2 organ riff in the studio, was the savior of the song. Something clicked for Dylan when it became more of a soulful rock n’ roll piece. Soft spoken, acoustic Dylan faded in the rear-view leaving a leather-studded electric version.
Sitting right at six minutes, radio stations initially hesitated to play it, but after being leaked to popular music clubs and landing in the hands of influential DJs, the hit climbed to a #2 spot on the charts. Fans felt perplexed, but further intrigued by Dylan’s rigidity against genre. You can now hear this cynical youthfulness in the words of Jesse Welles, Cameron Winter and Father John Misty — all modern-day reminders that carefully crafted lyricism can be one of the most powerful forms of influence, resistance and the will to keep going.
Wendell’s favorite song on the album is “Desolation Row,” and it isn’t close, a closer so commanding it sanctifies the opener, my favorite set of bookends on any record. After all the voltage and public sneering, Dylan snaps back to acoustic form, but not to folk comfort. Charlie McCoy’s guitar threads a dry, Spanish-tinted unease through the song, making the street feel foreign even as it’s instantly recognizable. The cast of fairy tales, movies, and books doesn’t feel surreal so much as indicted.
Highway 61 has already taught us this world, and now we see who winds up here: the punished, the curious, the stranded, all desperate, all hollowed out. Desolation isn’t collapse, it’s vacancy. You can hear the speed in it, thoughts racing, looping, needling medicine, sex, commerce, authority, then having the gall to ask which side you’re on while slipping out of reach himself. And if the melody sounds eternal, that’s because it is, sturdy enough that even Bruce Springsteen came knocking decades later, repurposing its haunted gait for the timely protest of “Streets of Minneapolis.” By the end, Dylan wants no replies, no debate, just letters from the void.
The scope was breathtaking then. It still is.
Bob Dylan’s work can be found here, and his music can be found on all streaming platforms and wherever records are sold. You are likely to find his songs played on SiriusXM stations Deep Tracks, The Village, The Loft, and Underground Garage. He last came through the area in July, Willie running the Outlaw tour, Dylan trailing, moving like someone determined to stay forever young. March revives the Rough and Rowdy Ways tour, grinding through towns that barely register a shadow. Atlanta sits out; Macon, April 22, is the closest. If you’re going, don’t think twice, don’t follow leaders, and watch your parking meters.
