On The Road is the original ‘Why I left New York’ essay


In a cosmic sense, I think it’s fair to blame Jack Kerouac for the glorification of Leaving New York. Ever since On The Road “defined a generation” in 1957, people exhausted by the hardscrabble urine-scented life of an NYC resident can feel validated, self-righteous even, over their decision to pack up and Go West, to set down new roots in the sunny climes of San Francisco and LA, or the laid-back liberal enclaves of Denver and Portland.

As Kerouac did (under the guise of “Sal” in On The Road) people who leave New York seem almost immediately overcome by the compulsion to write about their departure, and for all the other things OTR has become since its publicationβ€”an American classic, the signature novel of a social movement, a favorite book of recreational drug users everywhereβ€”it is also the OG of “Why I Left New York” rants. In his rambling and disorganized account of several years road-tripping back and forth across the country with Neal Cassady (Dean Moriarty in OTR) and a rotating cast of other since-canonized Beatniks (also represented by fictional alter egos), Kerouac beautifully romanticizes trading in his New York life (technically Paterson, NJ, but still) for a whirlwind and often penniless tour to and from and across the western half of the country, a tour filled with charismatic hitchhikers and negligent gas station attendants and drugs and alcohol and women and old friends whose wives are never happy to see Sal and Dean show up on their doorsteps.

On the Road has a reputation, as many books of this genre do, of being exhausting to read, or at least difficult to engage with. Kerouac wrote the novel as if writing a letter to a friend, and it feels like it: sentences run on and seem unedited, punctuation is sparse, characters are introduced with a presumed familiarity that makes the reader feel like they’ve stumbled across a stranger’s journal, not a book written for public consumption. But once acclimated to the formatβ€”sort of drug memoir meets travel diaryβ€”I found OTR engaging enough, like listening to a friend who’s had a few too many Red Bull/vodkas tell you about their European backpacking trip, or finding yourself on a long cab ride with a chatty driver who has a soothing voice and an interesting life story. While Kerouac wastes little energy on the character development of anyone except Dean (who is, more than anyone, the novel’s main character and most vibrant “creation”), it is the style and feel of On the Road that allows the reader to understand Sal, and in turn Kerouac, and to appreciate the former’s fictional insights as the latter’s real ones.

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