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From Grateful Dead to Bob Dylan: Five songs influenced by Jack Kerouac


“The only truth is music.” – Jack Kerouac

Now that the dust has settled on Jack Kerouac’s blustering travels, it has not only become clear that he is America’s true luminous literary nomad but also, with 1957’s On The Road, he may well have penned the most seminal novel of the 20th Century. Open any given modern copy, and you may well find Bob Dylan printed into the sleeve proclaiming, “It changed my life, like it changed everyone else’s.” 

Or perhaps it will be some other beatnik-spawn, proudly eulogising the trail that his life-giving prose blazed through the malaise of static predestined existence, bursting into bloom a bright new bohemian future for a thousand-fold army of disenfranchised youth aiming to tackle things a little differently from their forebearers. Their mantra seemingly: if we are to fail, then so be it, at least we did it on our own wavering terms. 

How, then, did his book prove so influential? Well, there are no doubt a myriad of reasons – the fickle fate of circumstance being one of them – but aside from that, what is obvious to observe is that it offered up the presentiment of a vibrant life beyond banality in a pretty monochrome world at the time. Aside from the endless misreadings, the scoffs of cynics and the analysis of its place in literature, the simple brooding pleasure of On The Road resides in the joy of life in motion and all the technicolour tones that whiz by. In short, the eternal duck soup thrill of being out there, living and breathing. 

Since 1957, this zeitgeist-basking appeal has never diminished. In Kerouac’s golden prose, he hightails his way through the high and lows, trials and tribulations, vistas and moments of effortless victory of rabidly relishing in culture. Naturally, this struck a chord with musicians. In fact, there is simply something lyrical about his prose itself—in Desolation Angels he wrote, “Music blends with the heartbeat universe and we forget the brain beat.” 

A million songs have flourished from such a feeling as he essentially fired up the engine of pop culture and gave youth a voice. His novel is proto-gonzo, proto-punk and without it, we probably would have Dylan, The Doors, David Bowie… Below we’ve curated five of the best songs that it inspired in a more direct sense. However, it is worth noting in a nebulous fashion, he probably spawned the entirety of modern music such was his seismic influence.

Five songs influenced by Jack Kerouac:

‘Light My Fire’ by The Doors

Speaking of not having The Doors without Kerouac, Ray Manzarek once said it almost exactly himself. “I suppose if Jack Kerouac had never written On The Road,” Manzarek once opined, “The Doors would never have existed.”

Morrison even described himself in a decidedly Kerouacian way: “I see myself as a huge fiery comet, a shooting star. Everyone stops, points up and gasps “Oh look at that!” Then- whoosh, and I’m gone…and they’ll never see anything like it ever again… and they won’t be able to forget me- ever.” The unfurling flourish came to the fore with The Doors’ first hit and helped to launch the band as a new literary rock ‘n’ roll force pouring something timeless into the effervescing zeitgeist.

‘Song to Woody’ by Bob Dylan

On Dylan’s debut album, his early stylings were already in place. “Walkin’ a road other men have gone down / I’m seeing your world of people and things / Your paupers and peasants and princes and kings,” he sings. And it is this particular couplet that brings his prose-like ways to the fore with crisp clarity.

Dedicated to one of his many heroes, Woody Guthrie, the line is a perfect mantra for the beatnik generation of which Dylan was one of the figureheads. It’s a line that could just as well have come from the novel that started it all, Jack Kerouac’s, On The Road. He’d go on to write ‘Desolation Row’ inspired, in part, by the novel Desolation Angels and a slew of other songs that hinted towards his literary hero in a literal sense. 

‘The Last Hotel’ by Patti Smith

Along with Thurston Moore and Lenny Kaye, Patti Smith helped to set some of the finest works in Jack Kerouac’s Poems of all Sizes anthology to music. Her punk delivery of the adapted pieces helped to bring a vitality to his already mystic words. However, the fact that the poems are barely changed is an indicator of just how musical he was as a writer and how he influenced musicians in turn. 

With his writing, he essentially took literature out onto the road in a very meta sense and abandoned traditional storytelling to reach out toward the people. The same can be said for the way that Patti Smith, originally a written word poet, abandoned the pen and got performative to be part of the punk zeitgeist

‘Black Peter’ by Grateful Dead

The reason that Kerouac and his beat compatriots can be said to have helped spawned pop culture is that they disavowed the stand-aside nature of artistry and went out there and brought it to the people with immediacy. They captured genuine culture on the wing and served it up just the same.

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The very literal wheelman of On The Road is dubbed Dean Moriarty (a somewhat annoying character oft responsible for misreads), and in a twist of fate, he was literally based on Neal Cassidy who was an actual wheelman once the Acid Test’s got going with Tom Wolfe and Ken Kesey spawning gonzo journalist in a sort of On The Road live blog (if it’s not too much of a sin to call it that) as Cassidy drove their technicolour tour bus around the States. 

The bus would stop at several gatherings where Kool-Aid containing acid was served up and the spun-out folks in attendance would take in a band bashing out rock ‘n’ roll. Their journey was a vehicle for counterculture and one of the bands absorbed in the gatherings was none other than Grateful Dead. Their acid anthem ‘Black Peter’ is almost an ode to Kerouac’s living breathing protagonist and the highs and lows of life on the road after lyricist Robert Hunter accidentally drank apple juice containing a $50,000 crystal of LSD

‘O’ City Lights’ by Gregory Alan Isakov

The album, Esperanza: Songs From Jack Kerouac’s Tristessa, pits indie artists alongside Kerouac’s novella, Tristessa. The short book documents a relationship with a drug-addicted Mexican prostitute. The prose is so lyrical in the unspooling tale that Kerouac’s nephew, Jim Sampas, a producer who has specialized in musical tributes, set about enlisting artists to transpose it to song. 

Sampas also produced the documentary One Fast Move Or I’m Gone: Kerouac’s Big Sur featuring the likes Ben Gibbard of Death Cab For Cutie, a noted mega-fan. “There’s a musicality in both his prose and poetry that worked well,” he commented. Indeed they do and it is fitting that now tributes to Kerouac come in all forms of medium, after all, he did help to break to the stilted walls of guarded and gave it the amorphous vibrancy that pop culture feeds off.

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