In which I review On the Road, Jack Kerouac’s celebrated 1957 novel about drugged up hipsters driving through 1940s America, hailed as the manifesto of the Beat Generation.

What it’s about: America, the late 1940s. Sal Paradise, a 20something college graduate and aspiring writer from New Jersey, travels to San Francisco after his divorce and meets Dean Moriarty, a charismatic drifter who is “tremendously excited with life.” Long for the freedom of the road, Sal hitchhikes to Denver and meets up with Dean, his young wife Marylou, the poet and philosopher Carlo Marx and their friends. The group travel to San Francisco where Sal divorces Marylou and marries his new love Camille. Sal continues his travels through California, having a brief relationship with a Mexican woman and working in cotton fields, before returning to New York. The following Christmas, Sal is in Virginia with relatives, where Dean turns up with Marylou, having abandoned Camille and their young daughter in San Francisco. Dean, Sal and Marylou return to New York, then travel to New Orleans where they visit Old Bull Lee and his wife Jane, who are drug addicts. Returning to San Francisco, Dean leaves Marylou to be with Camille. Sal and Marylou briefly consider living together, but she leaves. Sal and Dean meet again and visit jazz clubs, but a disillusioned Sal returns again to New York. A few months later, a depressed Sal returns to San Francisco in search of Dean. Camille is pregnant and unhappy while Dean has injured his thumb in a fight with Marylou. Sal and Dean take a third road trip through California and back to Denver. Dean finds a job driving a Cadillac to Chicago and drives most of the way at manic speed, delivering the car in a disheveled state. They return to New Jersey, where Dean meets a woman named Inez and gets her pregnant. A year later, Dean is still in New York, living with Inez and their child and working as a parking attendant. Sal takes to the road again, and returns to Denver, planning a trip to Mexico with his friend Stan. Dean joins them in a new car and the trio drive through Texas and into Mexico, where they enjoy the desert landscape, easy access to drugs and a night in a brothel. Sal falls seriously ill with dysentery, and is abandoned by Dean who returns to America. Sal recovers and returns to New York. Dean, having obtained his divorce papers in Mexico, returns to New York to marry Inez, but quickly leaves her and returns to San Francisco and Camille. Sal and his new girlfriend Laura decide to move to San Francisco. Dean offers to help them move but turns up five weeks early, before Sal has enough money to move. Sal says goodbye to Dean, who is returning to San Francisco, and goes to a Duke Ellington concert with Laura and his friends, pondering his friendship with Dean who we are told he will never see again.

Why it’s a classic: There are few American novels more revered than On The Road, a book that was to the 20th century what Thoreau’s Walden was to the previous century: a hymn to the myth of American exceptionalism and a celebration of the wide open spaces of the landscape, told by a privileged white male who chooses to push against the dominant culture of his time.

Even the story of how On the Road was written has become mythologised: Kerouac created a 120-foot scroll of tracing paper, threaded it through his typewriter and wrote the first draft in a continuous three-week binge, fuelled by coffee, alcohol and Benzedrine, leaving out punctuation and paragraph breaks. (The original scroll was purchased in 2001 for US$2.3 million and is occasionally displayed in museums and libraries). The truth was rather more prosaic – Kerouac had been working on the book for nearly nine years, and spent a number of years re-writing the original scroll manuscript, deleting a number of sexual passages that would have made the book unpublishable.

On the Road was published in 1957 to mixed reviews, though it was championed by Gilbert Millstein in the New York Times as a major novel and an authentic new voice in modern American fiction. The book was hailed for personifying the values of a disaffected new generation who kicked against the austerity and conformity of Eisenhower-era America in favour of a search for personal freedom and heightened individual experiences. Ever the contrarian, Kerouac kicked against these classifications, saying famously, “I’m not a Beatnik; I’m a Catholic“, while enjoying the adulation his fame brought him. Kerouac died just 12 years later from complications due to alcoholism, aged just 47, adding further to the “live free or die” myth around his life and work.

Since then, nearly every major cultural figure of the post-WWII era has cited Kerouac and On the Road as an inspiration. Bob Dylan said “It changed my life like it changed everyone else’s”. David Bowie claimed that reading On the Road aged 15 encouraged him to leave suburban south London and make a name for himself. Rock musicians The Beatles, The Doors, Tom Waits, Van Morrison and Patti Smith have cited the book’s style and subject matter as a major influence on their work. Kerouac’s freewheeling jazz-inflected prose and his vision of adventure and rebellion more or less single-handedly kicked off a new style American prose – rambling drug-infused narratives, Existentialist-lite protagonists whose heroism stems from their anti-establishment refusal to be heroic, and an interest in then-taboo subjects like sex, drugs, irresponsible driving and Buddhism.

On the Road casts a very long shadow over the last 60 years of American culture. Kerouac’s style and sensibility can be seen in the works of Hunter S Thompson, Ken Kesey, Richard Brattigan, Thomas Pynchon and Charles Bukowski, and in countless Hollywood road movies from Butch Cassidy and the Sundance Kid and Paris, Texas to Thelma & Louise. Perhaps inevitably, filmmakers have spent decades trying to bring On the Road to the screen. Kerouac wanted Marlon Brando – another anti-establishment icon of the 1950s – to play Dean, with Kerouac himself playing Sal, though fortunately that didn’t pan out. Francis Ford Coppola bought the film rights in 1979 and spent thirty years trying to get a new project greenlit, eventually passing the project to Brazilian director Walter Salles. The Salles-directed film, starring relative unknowns Sam Riley as Sal and Garrett Hedlund as Dean, was released in 2012 and received respectable if not ecstatic reviews and limited box office success – suggesting that the Cult of Kerouac had lost its power to shock, becoming yet another relic of Baby Boomer nostalgia.

Bouquet or Brickbat: A bouquet of Benzadrine tablets, washed down with cactus juice. When I announced on social media that my next Dead White Males book would be On the Road, a straight male friend commented that it had inspired him to hitchhike across the country, jump trains and live like a beggar, until finally heading back to his mum’s place for a shower. It’s responses like those that’s made me avoid Kerouac like the plague till now. Viewed through a post-hippie, post-feminist lens, he’s come to represent a high-spirited but repellent type of white heterosexual male artist, noisily proclaiming himself as a prophet and a rebel while coasting blind to his own privileges and casual misogyny.

This to some extent is the problem with encountering On the Road in 2021. It’s nearly impossible for us to imagine ourselves back into the austerity of 1950s America, when Kerouac’s freewheeling prose style and casual referencing of drug-taking, bed-hopping and homosexuality caused genuine outrage. His story of young men going wild took such firm hold on the cultural aspirations of the Baby Boomers that we now see it as a canonical text rather than an interesting literary experiment. The real-life writers whose lives he loosely fictionalised – Neal Cassady (Dean), Alan Ginsberg (Carlo Marx) and William Burroughs (Old Bull) – become fellow patron saints of the Beat Generation, and so On the Road has become a creation myth for that cultural movement, along with Ginsberg’s poem Howl and Burroughs’ novel The Naked Lunch.

Now that we’re on the other side of 1960s counter-culture and “OK Boomer!” is now a thing, we can finally shake off some of the reverence accorded to Kerouac, view his work with some critical distance and ponder on its many failures and omissions. We’re now much more likely to eye-roll as Dean yabbers away deliriously about their search for “IT” and Sal says “for just a moment I had reached the point of ecstasy that I always wanted to reach, which was the complete step across chronological time into timeless shadows, and wonderment in the bleakness of the mortal realm.” We can cringe at Sal’s imaginative identification with indigenous peoples, whose lives he romanticises and barely understands. We can also take Kerouac to task for his disposable female characters, and wonder what life might actually have been like for Marylou, Camille, Inez, Sal’s unnamed Mexican girlfriend, all the “whores” who litter the book like tossed-away cigarettes, or what happened to Dean’s four forgotten children. And if we’re feeling really misanthropic, we can wag a finger at the life of excess Kerouac describes, which led to his early death.

Then there’s the lingering homoeroticism of On the Road, which is essentially a love story between two “straight” men. Despite all his macho posturing, Kerouac’s bisexuality has now been conclusively established: he had an on-off sexual relationship with Cassady for nearly 20 years, as well as briefer affairs with Ginsberg and Burroughs. In his book Subterranean Kerouac, biographer Ellis Amburn called him a “homophobic homoerotic” – a guilt-ridden Catholic who concealed his bisexuality via gay-bashing on the page. The sexual undertow of On the Road is very strange: while Sal and Dean refer contemptuously to “queers” and “fags” and Dean calls New York “a frosty fagtown“, we’re also made aware that he turns tricks with men to make cash. Even more apparent is Sal’s adoration of Dean. The narration sparks to life whenever Dean is around, and our attention is drawn to his muscular body and joie de vivre; by contrast, Sal’s descriptions of the many women he meets feel pedestrian and uninspired, more schoolboy fantasies than living flesh-and-blood romances. The strength of On the Road, and the source of much of its tragedy, comes mostly from the sparks that fly between Sal and Dean, two men who love and need each other but who are too conflicted and damaged to make it work.

So, given its pretentiousness, sexism, racial stereotyping, sexual dishonesty and general toxic white male wankery, is there anything in On the Road worth praising? Hell, yes! Despite all my woke sensibilities telling me not to love this book, I couldn’t help but admire it, for its energy and ambition and freewheeling sense of abandon. It also helped, I think, to read it during a COVID-enforced lockdown, in which I could thrill to the young protagonists’ sense of freedom and irresponsibility, and their apparent fearlessness even in the face of their own obliteration. I was reminded of Laurie Lee’s As I Walked Out One Midsummer Morning (another picaresque male adventure across an unforgiving landscape), reminiscing about the effortless energy of youth: “I was at that age which feels neither strain nor friction, when the body burns magic fuels, so that it seems to glide in warm air, about a foot off the ground, smoothly obeying its intuitions.”

I was also amazed by how literate and literary it was – far from being the ravings of a drug addict after a three-week writing spree, On the Road is a thoughtful, crafted and consciously poetic work, packed with references to the greats of American literature. Walt Whitman, Mark Twain, Herman Melville, Jack London, William Faulkner, Ernest Hemingway and William Saroyan are all name-checked or alluded to, and the early parts of the story attempt to capture the hard-scrabble existence of post-WWII Americana described so movingly in Steinbeck’s Dust Bowl novels. There’s a carefully planted reference to Marcel Proust at the end, and there’s certainly something of Proust in Kerouac’s long rambling descriptions of the sensory experiences of life, and his persistent melancholia about lost time.

Occasionally, too, Kerouac gives his heroes a run for their money with some truly stunning writing. He’s particularly good on describing the Mississippi River, with the kind of mythological resonance of Faulkner on a good day: “From bushy shores where infinitesimal men fished with sticks, and from delta sleeps that stretched up along the reddening land, the big humpbacked river with its mainstream leaping came coiling around Algiers like a snake, with a nameless rumble. Drowsy, peninsular Algiers with all her bees and shanties was like to be washed away someday. The sun slanted, bugs flip-flopped, the awful waters groaned.”

Perhaps because I’m now in middle-age, with no desire to identify with Kerouac or emulate his adventures, I can read On the Road more sympathetically, as a book about failure. Sal and Dean, like their real-life counterparts, are searching for some kind of transcendence. “Somewhere along the line I knew there would be girls, visions, everything,” Sal writes, “somewhere along the line the pearl would be handed to me.” The tragedy of the book lies in the fact of their failing to ever find what they seek. Sal seems to come close, lying on his back on top of a car in the hot Mexican night: “I went back to my bed of steel and stretched out with my arms spread. I didn’t even know if branches or open sky were directly above me, and it made no difference. I opened my mouth to it and drew deep breaths of jungle atmosphere. It was not air, never air, but the palpable and living emanation of trees and swamp.” Then he thinks he see a white horse, but is unclear if it’s a dream.

It’s a truly pathetic moment – Sal’s (and Kerouac’s) need to find some kind of unifying metaphor is so great that he descends into bathos and cliché. The reality of their situation – Sal falling ill with dysentery and Dean abandoning the person he claims to love, yet again – to some extent cuts through all the pseudo-Buddhist philosophising and exposes the fallacy of their adventures. We have to give Kerouac credit for this insight. It was his readers, rather than him, who embraced On the Road as a guide to self-enlightenment, and it’s possible he meant the book to be read more ambiguously.

I’m also struck by the power of the images of “Home” that resonate through the book. Like most youngsters who want to change the world, Sal is initially contemptuous of the institution of family, describing his relatives in Virginia as “gaunt men and women with the old Southern soil in their eyes, talking in low whining voices about the weather the crops, and the general weary capitulation of who had a baby, who got a new house, and so on“. But this world of home, family and children is inescapable, and something that Sal and Dean long for and return to again and again – Sal to the sense of security provided by his aunt and then by Laura, and Dean to one of his many fractured marriages. One of the book’s most resonant themes is Dean’s continual search for his wino father, who is never found: “Somewhere behind us or in front of us in the huge night his father lay drunk under a bush, and no doubt about it – spittle on his chin, water on his pants, molasses in his ears, scabs on his nose, maybe blood in his hair and the moon shining down on him.” This desire for the lost authority figure, whether real or Freudian, haunts the book until its final line, undercutting a simplistic reading of the book as an escape into adventure and freedom. Like Dorothy in The Wizard of Oz – another canonical American tale laden with queer subtext – perhaps the saddest lesson of On the Road is that try though you may to escape, there’s no place like home.

Quotable Quote: “As a seaman I used to think of the waves rushing beneath the shell of the ship and the bottomless deeps thereunder–now I could feel the road some twenty inches beneath me, unfurling and flying and hissing at incredible speeds across the groaning continent with that mad Ahab at the wheel. When I closed my eyes all I could see was the road unwinding into me. When I opened them I saw flashing shadows of trees vibrating on the floor of the car. There was no escaping it. I resigned myself to all.”