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 publication—an American classic, the signature novel of a social movement, a favorite book of recreational drug users everywhere—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 format—sort of drug memoir meets travel diary—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.

OTR, in a way that reminded me of Tropic of Cancer, is an exaltation of Dean and Sal’s free-spirited cavorting. They travel not in the hopes of moving somewhere else, or finding something or someone in particular, but simply to travel, to live in the way that only people without defined goals and predetermined timetables can. Whether or not you consider the nomadic life enviable (I don’t personally, and found myself identifying most with Sal’s quiet homebody aunt), it is easy to envy the way Sal and Dean let go, the way either or both of them will set off on a cross-country journey with little more than 10 sandwiches and $10. It doesn’t take a Beatnik heart to respect a little Beatnik spirit.

But On the Road can also be sad, and Dean and Sal’s constant need for something different, something new and fun and crazy, wreaks havoc on their relationships with others. “I’ve shambled all my life after people who interest me,” Sal says early in the novel. “Because the only people for me are the mad ones, the ones who are mad to live, mad to talk, mad to be saved, desirous of everything at the same time, the ones who never yawn or say a commonplace thing, but burn, burn, burn like fabulous yellow roman candles exploding like spiders across the stars.” It’s easy to see how Sal’s recipe for life is both exciting and alienating, a dichotomy with a long history of inspiring great art, and great drug use.

On the Road is one of those books that probably evokes different emotions depending on when in your life you read it. I’ve always been neurotic and spontaneity-averse—my own road trip through San Francisco, Denver and Portland involved a year of planning and at least one spreadsheet—but I can imagine a less uptight teenager or young adult finding in OTR a crucial blueprint for living life the way it’s meant to be lived. Years later, that person might read the same novel as a parent and see it in a different light, might worry about Sal hopping into cars with strangers (in fairness, this was the 1940s), might sympathize with the aunt who has to keep sending him $50 so he doesn’t get stranded mid-trip. In the golden years of one’s life, On The Road could become a nostalgia trip to simpler, youthful times, or an unfortunate reminder that one took too few chances, and didn’t throw caution to the wind often enough.

But what makes On The Road timeless is not its much-celebrated notion of travel, of throwing a suitcase in the back of a pickup and heading West with a quarter-tank of gas, no heat and one loaf of bread. What makes the novel resonate today is its suggestion that life doesn’t have to be about success, or rather, that success doesn’t have to mean wealth and recognition. When he first sets off with Dean, Sal is a budding writer already; he has a half-finished manuscript whose completion and sale to a publisher a few years later earns little more than a six-word mention in OTR. Because for Sal, for Kerouac, being on the road isn’t about pausing one’s ascent on the career ladder; it’s about understanding that there doesn’t have to be a ladder.

Kerouac in 1956

Which brings us back to the Leaving New York narrative. In a piece for the Daily News last week, someone described New York to author Christopher Ketcham, (who recently left the city for a small town in Colorado) as “almost entirely about money” and “a dead place full of people so tired and overworked they don’t remember what it feels like to feel good.” In a 2010 talk at Cooper Union, Patti Smith (whose Just Kids takes place in 1960-1970s NYC) said the city “has closed itself off to the young and the struggling.” In an essay for The Guardian, Moby, a native New Yorker who moved to LA a few years ago, said New York is “exclusively about success. …There’s a sense that New Yorkers never fail, but if they do, they’re exorcised from memory, kind of like Trotsky in early pictures of the Soviet Communist Politburo.”

Indeed, the reigning motif of the goodbye New York letter isn’t the crowds, or the rats, or the amount of time one spends each week trying to identify puddles of opaque liquid. These things factor in—how could they not?—but they are also, for many New Yorkers, a source of what Kerouac calls a “wacky comradeship” here. As Cord Jefferson wrote in a surprisingly tolerable farewell NY essay for Gawker, “the tumult the City throws in your way daily engenders a sense of community the way getting its ass kicked on a rink might galvanize a hockey team.”

It’s true: We expect to be at war with our city in certain ways—the ever-shifting train routes, the umbrellas that give way mid-storm, the paper coffee-cart cup with a leak you don’t notice until it’s ruined your white button-down. What so many can’t stomach aren’t the day-to-day indignities of being a New Yorker, but rather the city’s ever-larger concessions to wealth, its broad shift toward monied interests that have made their impact known in everything from rents to retail outlets to the highest income gap in the nation. New York City has always been about “succeeding in spite of,” but in spite of what—a detour on the F train, or getting evicted from your $1,500-a-month roach-infested studio? Moreover, why define success on these terms in the first place? Why cherish clutter over space, possessions over possibilities, opaque puddles of liquid over wide open skies?

I could write an entirely separate piece on the Leaving New York Essay (as the New York Times did last fall), in which I’d note that what’s happened here is simply a microcosm of what’s happened in the U.S. as a whole over the last 20 years. I could talk about how, for all its luxurious excess, New York is also still a fine purveyor of cheap alcohol and delicious, authentic cheap food, if one takes the time to look for them. I could recommend a tour through the listings in Time Out or on MeetUp as evidence that the city has no shortage of creativity, of artists and dreamers and people who perform plays in warehouses or do sketch comedy in basement apartments or make their living owning stores entirely dedicated to pickles or buttons or anatomical artifacts. I’m not saying New York doesn’t have serious socioeconomic discrepancies—and I appreciate that I occupy a privileged pocket amid the city’s admittedly punishing rhythms—but New York still is, and I suspect will always be, the place I’m supposed to be, the crowded asylum of fellow neurotics with whom I am supposed to share ever-smaller amounts of space and air, and ever-fewer seats at the dive bars. As a fatalist of some measure, I am being only mildly facetious when I say that New York is where I want to be when the world ends—I picture myself overtaken by a tsunami while in line at Duane Reade, grumbling with fellow New Yorkers about the single open register.

Read simply as a book, with no acknowledgment of its literary import, On the Road is good, a memorable tour through the psyche of charismatic friends in the pivotal middle of the 20th century. Read as a classic, as the “novel that defined a generation,” it is a prophetic hint at the cultural revolution that was soon to take hold in America, and an impactful exploration at the way one chooses to live life: cautious, prepared, driven; or carefree, impulsive, in the sheer pursuit of happiness. I suspect that for most people, the ideal lies somewhere in the middle of that spectrum, somewhere between Kerouac and his aunt, between New York and Portland. On the Road simply asks us to ask ourselves whether we might sometimes choose the carefree path, might sometimes cede stability or success for fun, for the fleeting adrenaline of unplanned experience. “What is that feeling,” Sal asks, “when you’re driving away from people and they recede on the plain till you see their specks dispersing? It’s the too-huge world vaulting us, and it’s good-by. But we lean forward to the next crazy venture beneath the skies.”


TITLE: On The Road
AUTHOR: Jack Kerouac
PAGES: 310 (in paperback)
ALSO WROTE: The Dharma Bums, Big Sur 
SORTA LIKE: Tropic of Cancer meets Road Trip
FIRST LINE: “I first met Dean not long after my wife and I split up.”

9 thoughts on “On The Road is the original ‘Why I left New York’ essay”

  1. Nice post, enjoyed reading it. Really do have to get some more Kerouac in. As far as NY goes I’m ready to get out myself. Was born and raised in Brooklyn and almost nothing I enjoyed about it is left. Enjoy the dive bars while they last, probably wont be much longer.

  2. Where do I start….I read. I do nothing but read. I wish I could review what I read but it is a faculty I lack. I was blogging away about my life on this site and decided I should find someone to follow. My interest is books and only books. Only 21 book blogs were available and as I went through them I was disappointed, none appealed. And then, I found yours and read down through and instantly had the impulse to follow. I am not young, I read On The Road so long ago I cannot remember anything about it but you brought it back vividly. Thanks for the pleasure.

    1. Thank you so much; what a lovely comment. I’m literally going to turn off the Internet now and read nothing else so this is my final impression of the day.

  3. Nice post! Reminds me of Joan Didion’s essay “Goodbye to All That.” Personally, I wasn’t a huge fan of Kerouac’s OTR when I read it a couple years ago, but I love the spirit of his writing – the impulse to ‘light out for the territories.’

  4. I read On The Road about a year ago. You’re spot on. The run-on’s, the punctuation, almost makes it hard to get into. However, there is no denying it is a landmark book and a must read for anyone who needs a kick in the ass if they want a life change.

  5. This was probably the most well composed articulation of Kerouac’s OTR I have ever read.

    I took a class at Cornell called “On the Road: From the Beatniks to the Hippies” and ran away from home my freshman year after feeling so inspired by this classic. You really nailed “it” on it’s head.

    And the comment about Duane Reade….maybe the single biggest affirmation that New Yorkers have unrealistic expectations.

    1. Thank you! …Though I can’t tell if you’re suggesting a tsunami *won’t* take me when I’m in line at DR. I think there’s a solid chance!

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