‘Desolation Row’: Understanding Bob Dylan’s dystopian epic

Ever since his wearily-travelled boot stepped foot in the thriving cafes of the Greenwich Village folk revival scene, the weight of the world has hung from every word uttered by Bob Dylan. Razor-sharp observational wit oozed from his seminal folk record, The Freewheelin’ Bob Dylan, but it was when he plugged in for Highway 61 Revisited that he staked his claim as the fearless leader of music’s movement to become a politicised force.

Like all who rise to the top seats of royalty, Dylan did so battered and bruised. His brutal albeit necessary U-turn on the folk community with his 1965 electric record subjected him to several cries of “Judas”. But Dylan’s third eye always allowed him to weather artistic storms with unwavering strength, bolstering his claim as the new observational voice of a generation.

While sonically, the record was a flag placed firmly in the future, the kernel of its idea existed deep within Dylan’s past and a return to his roots. “Highway 61 begins about where I came from, Duluth, to be exact,” Dylan explains in his memoir, Chronicles One, regarding the album’s literal origin.

He adds, “I always felt like I’d started on it, always had been on it, and could go anywhere from it.”

Something about that backwards introspective journey allowed the record to draw from life’s broader themes. An idea showcased perhaps no finer on the record’s most famous moment, ‘Like a Rolling Stone‘, musing on someone who had lost their spiritual guidance with “no direction home”. 

But while Highway 61 was largely the path upon which Dylan’s enlightenment would be beaten, his epic closer ‘Desolation Row’ soars beyond human conventions and instead draws on something more dystopic altogether. 

Bob Dylan - 1960s
Credit: Far Out / Alamy

Across its 11 published verses, the song introduces a rolling cast of characters, including Robin Hood, Cinderella, the Good Samaritan, and Cain and Abel, in a bid to ultimately debase the declining landscape of idealist America.

While Dylan hasn’t been naive enough to give any background information to the real whereabouts of ‘Desolation Row’, the guitarist who played on the track, Al Kooper, explained that some influence came from an area on Eighth Avenue in Manhattan, described as “an area infested with whore houses, sleazy bars and porno supermarkets totally beyond renovation or redemption,” according to Mark Polizzotti in his book Highway 61 Revisited.

It’s a fitting location of influence for Dylan to intellectually take down the very roots of America’s rapidly expanding capitalism, with the sort of underhanded scathing that its very recipients perhaps couldn’t comprehend.

It comes as somewhat of a surprise to die-hard Dylan fans, who connect his every word to the higher echelons of literature that he used Cinderella and Robin Hood as thematic references. “Cinderella, she seems so easy, it takes one to know one she smiles / And puts her hands in her back pockets Bette Davis style”, he sings on a second verse that ends with, “And the only sound that’s left after the ambulances go / Is Cinderella sweeping up on Desolation Row”.

The lost allure of fairytale figures, along with an Einstein whose genius has faded and a Casanova who has been killed, is what contextualises a world where social order has decayed. The post-“happily ever after” ending of modern America has given way to a Cinderella whose childlike naivety has devolved into cynical quips, and the glass slipper has been replaced by a broom fit to sweep a broken road.

The remainder of the track ebbs and flows through three separate acts, which all include canonised literary and mythological figures whose expected journey has been turned on its head. By the song’s third act, his despairing ballad comes to its conclusion with the line, “The Titanic sails at dawn / And everybody’s shouting / ‘Which Side Are You On?’”. The ship of America is plummeting to murky depths, yet still preoccupied with the divisions that have plagued the progress of its society for decades, bringing a potent and realistic end to an otherwise entertaining cautionary nightmare disguised as a fairytale.

Growing inequality of wealth and rapidly expanding sentiments of fascism were thrusting American citizens past the point of reasonable discussion. Such was Dylan’s perspective of the ridiculousness of the societal situation in which he placed his observation in the dystopic and esoteric in the hopes that, in the midst of all the narrative entertainment, his concerns may actually be heard.

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