Jack Kerouac – anti-establishment icon, revolutionary author of the American classic On the Road, pioneer of the Beat Generation and, perhaps most of all, enduring symbol of cool.
If a dog-eared paperback of On the Road slung in your back pocket was once the ultimate avant-garde accessory, 100 years after his birth, a Kerouac namecheck has become something of a trope on dating apps. New analysis by OkCupid has shown that mentions of the Beat poets and On the Road in profiles (more often on those belonging to men) have increased more than threefold in the past five years.
With their themes of travelling, male friendship and flight from the nine-to-five to explore a world of sex, drugs and art, it’s easy to see why men want to align themselves with Kerouac’s books. The anarchist ideals of On the Road characters Dean Moriarty and Sal Paradise are ones that “alternative” or “indie” communities have often shared.
As a result, Kerouac remains present in popular culture like few other authors: his face appears on Christian Dior sweatshirts, as recently worn by Benedict Cumberbatch; his book The Dharma Bums features in the TV show Ted Lasso; and British band the 1975 took their name from random scribbles on the back page of On the Road (“1 June The 1975”).
Amid record-high rates of job resignations and a reported “vibe shift”, a renewed interest in Kerouac suggests a post-pandemic revival of the Beatnik spirit – of casting off the shackles of convention to chase down the spirit of Dean Moriarty.
But insofar as Kerouac is invoked as a symbol, his meaning is not uniformly understood. To some, he is an aspirational iconoclast; to others he is the face of white male privilege. His alter ego Sal Paradise may have been inspired by his time working on a farm in California, for example, but he always had the option of returning home, or of being sent money by his aunt. Kerouac himself was a white, university-educated man who returned from his travels to have his meals cooked and his washing done by his mother.
Moreover, sixty-five years since publication, the misogyny of On the Road looks overt, even gleeful: Moriarty’s “awfully dumb” 16-year-old wife Marylou is instructed “to make breakfast and sweep the floor” within the first three pages.
Holly George-Warren, author of a forthcoming authorised Kerouac biography, says he depicted women as “objects of the male gaze and little else”, and drew from racist tropes in “romanticising the ‘other’” – for instance when Sal and Dean see freedom in the way that Mexican people live. Readers today may find these things repellent, George-Warren acknowledges, but it is only one aspect of the complicated and often contradictory author.
As much as Kerouac benefited from his privilege, elsewhere he rails against it. “He explored gender, sexuality and queerness openly in his work during a time when to do so was very rare … and he did write with deep empathy about marginalised people,” says George-Warren.
An unqualified passion for Kerouac has nonetheless come to register as a red flag to some straight women swiping through potential partners, as a staple of “straight male reading culture”.
His reputation is such that he is just as often invoked to signify tortured masculinity imposed on long-suffering women as he is for his pioneering writing. In the TV show Gilmore Girls, for example, Paris admonishes Jess for his “typical guy response” to the Beats’ drug-fuelled bromance, and, in Mad Men, the womaniser Don Draper sees Kerouac in a hallucination.
This kind of “bro-ish” love of Kerouac can be seen as an adolescent phase. As writer Helena Fitzgerald wrote in praise of getting older for Electric Lit: “Nobody has tried to talk to me about Jack Kerouac in at least five years.”
But the image of the author that people are repelled by or drawn to – the all-American, hyper-masculine hero of the open road – “is the myth of Kerouac”, not the reality, says Jean-Christophe Cloutier, an associate professor of English at the University of Pennsylvania.
Kerouac was handsome and a talented football player. But he was also the son of working-class Catholic immigrants from Québec. Jean-Louis, as Kerouac was born, did not learn English until he was six years old, and struggled through most of his teens. Cloutier, himself Québécois, has translated Kerouac’s French novellas and says the author felt outside American culture all his life.
On the Road becomes a different journey when read from this marginalised perspective. But the mythologising of Kerouac was almost instantaneous on its publication in 1957, with a rapturous New York Times review declaring it the “most important utterance yet” of the Beat generation. The author “didn’t help himself”, acknowledges Cloutier, by claiming to have written it in just three weeks, leading to Truman Capote’s well-known dismissal: “that’s not writing, that’s typing.”
Presented with a bona fide movement, the media machine went into overdrive, peaking with the Village Voice’s “Rent-a-Beatnik” stunt in 1959, where arty types were hired to attend parties for $40 a night. Kerouac’s literary achievement was inseparable from his commercial one: as William Burroughs wrote, “On the Road sold a trillion Levis and a million espresso machines, and also sent countless kids on the road.”
For Kerouac, success was a bitter pill with which he struggled until his death in 1969, aged just 47, after more than a decade of alcoholism. “It was one of his great sadnesses … [The Beats] were so against materialism and consumer culture, and here they are being co-opted,” says Cloutier.
It was precisely that countercultural cachet that made them such an enduring brand, as evinced by the Gap’s 1993 “Kerouac wore khakis” campaign.
But where Kerouac the myth was marketable, the man was emphatically not. Portrayed as a hard-living free spirit, Kerouac was in fact dedicated to his craft and lived a mostly “monastic life” with his mother and his Persian cat Tyke.
It’s probably not this Kerouac – “the bilingual, struggling, poor, reclusive” writer, whose cat was his “baby” – being swiped through on dating apps, points out Cloutier. But that is the double-edged sword of iconic status: few authors are so well known or as widely misunderstood.
As Kerouac’s friend Seymour Krim wrote after his death, he was a “bleeding ball of contradictions” that cost him all his life: “Kerouac had myth to him all right … but it only came through his remarkable ability to become his own ‘true’ self on paper.”
In this commitment to honest self-expression – what Kerouac termed creating a “telepathic shock” with his reader – he inspired a greater range of artists than he is sometimes given credit for: David Bowie and Bob Dylan, yes, but also Haruki Murakami, Hanif Kureishi, Lana Del Rey, writers of autofiction and even feminist works of art.
Introduced, inevitably, to Kerouac by her then-husband Russell Brand, Katy Perry wrote Firework, an empowering pop song about Sal Paradise’s paean to people who “burn like fabulous yellow roman candles”. And the original millennial feminist, Lisa Simpson, has On the Road on her bookshelf. Alison Bechdel, in her latest graphic memoir The Secret to Superhuman Strength, writes of being inspired by The Dharma Bums to climb a mountain and “make a drastic change” in her life.
Much of Kerouac’s work does not pass Bechdel’s eponymous test for female representation. Cloutier notes, however, that the “earliest and best” Beat scholars were women: Ann Charters, Regina Weinreich, Nancy Grace, and Joyce Johnson (who wrote Minor Characters about her relationship with Kerouac and his work). “There’s a way to look at it beyond gender,” insists Cloutier of On the Road, “As a journey of discovery for any human being – and one being undertaken with ultimate candour.”
It might be that what some find hard to stomach about Kerouac is not his writing, not even the man himself, but his brand and its fans. In the face of the spirited dudebro defence, readers often miss Kerouac’s spirituality and his respect for nature, says George-Warren – even his emergent climate consciousness. “His anti-materialism, very rare during the postwar years … predicted what over-consumption has done to the planet.”
And Cloutier suggests that the Beats’ anti-conformist message is especially relevant now, as binary public debates and insidious algorithms make it harder than ever to think for oneself. If you can get away from the image, read his books, get that telepathic shock – he can be a companion on any journey,” says Cloutier.
One hundred years after his birth, it’s time to see beyond sweatshirt Kerouac to the “strange solitary crazy Catholic mystic” he saw himself as. But whether that would be any more successful on a dating profile I couldn’t tell you.
• A Clothbound Classic edition of On the Road to mark Kerouac’s centennial has been published by Penguin (£16.99). To support the Guardian and Observer order your copy at guardianbookshop.com. Delivery charges may apply. Holly George-Warren’s Jack Kerouac biography will be published in 2024 by Allen Lane.
