How Jack Kerouac’s dreams of being the American Proust were ruined by liquor

One hundred years ago, on March 12 1922, while Marcel Proust was lying in his cork-lined bedroom on the Boulevard Haussmann with months to live, racing his failing health to complete the final volumes of À la Recherche du Temps Perdu, a boy was born on the other side of the world in Pawtucketville, the French-speaking quarter of Lowell, Massachusetts, 25 miles outside Boston. Jean-Louis Kerouac was the son of French Canadians who traced their ancestry (via generations of potato farmers) to an 18th-century Breton prince and the tiny French hamlet of Kerouac, between Quimper and Quimperlé in Brittany.

Petit Jean knew from an early age that he was destined to be a writer. “Had beautiful childhood,” he recalled, “[…] first novel written at age 11.” As a child he was nicknamed Memory Babe because of his ability to remember details, and he had an imaginary friend called Doctor Sax, his “ghost, personal angel, private shadow, secret lover”, around whom he wove a complex mythology. He grew up speaking French at home, only becoming fluent in English in his late teens – and at school he adopted the name Jack.

Jack Kerouac’s life changed at the age of 18, when he moved to New York to study at Columbia University. He met Allen Ginsberg, William S Burroughs and other aspiring writers, and began preparing seriously for his life as an author. He prescribed himself a schedule of “required reading”, which included the Bible, the complete works of Shakespeare (“again”), Thomas Wolfe (“always”), Joyce’s newly published Finnegans Wake and “Proust’s Remembrance”. He cut classes in order to read, or roam around the city on crutches – after breaking a leg playing football – visiting scenes from Wolfe’s novels. He aspired to be, like Jack London, both an author and an adventurer; “a lonesome traveller”.

It was Kerouac who suggested the term Beat Generation to describe himself and his contemporaries. “More than mere weariness, it implies the feeling of having been used, of being raw,” wrote his friend John Clellon Holmes. “It involves a sort of nakedness of mind, and, ultimately, of soul: a feeling of being reduced to the bedrock of consciousness.”

“Nobody knows whether we were catalysts or invented something, or just the froth riding on a wave of its own,” mused Ginsberg. “We were all three, I suppose.”

In 1946, Kerouac met Neal Cassady, a young ex-convict (“burning shuddering frightful”) and they began making a series of orgiastic, melancholic, beatific road trips across America. Five years later, inspired by a wild letter from Cassady, Kerouac sat down to transcribe their adventures: he taped together strips of drawing paper to form a continuous, 120ft long sheet which scrolled through his machine as he typed uninterruptedly for three weeks, stoked on Benzedrine, cigarettes and pea soup. The result was a feverish work of “spontaneous prose”, his distinctive blend of jazz improvisation, prodigious recall, inspired poetics and performative chutzpah.

Despite Truman Capote’s acerbic comment – “that’s not writing, it’s typing” – the spontaneous method became Kerouac’s vocation. It took him six years to get his scroll published as On the Road; in the meantime, he wrote Visions of Gerard, about his saint-like older brother, who died at the age of nine; Doctor Sax and Maggie Cassidy, about his childhood in Lowell; and The Subterraneans and Tristessa about later love affairs. All of these he wrote remarkably quickly – he completed The Subterraneans in just three nights – and all of them are highly autobiographical, with Kerouac appearing, usually, under the name Duluoz (French Canadian for “the louse”).

He began to conceive of these works as chapters in a single “contemporary history record”, modelled on Proust and called The Duluoz Legend. “Goddamit,” he wrote in his journal, “I want to use the Proustian method of recollection and amazement but as I go along in life, not after.”

In 1955 he wrote to his editor, Malcolm Cowley: “Everything from now on belongs to The Duluoz Legend. […] When I’m done, in about 10, 15 years, it will cover all the years of my life, like Proust, but done on the run, a Running Proust.”

On the Road was finally published in 1957 and Kerouac’s life changed again. America was at a cultural crossroads in the late 1950s: below the post-war rise in suburban affluence ran a seam of youthful discontent, raising profound questions around civil rights, gender equality and the vacuity of the American materialist dream. Kerouac’s radical vision of “illuminated hipsters” spoke directly to this disenchanted, beat generation. The book became a cult phenomenon and he became a rebel icon.

On the Road combines majestic descriptions of the American landscape with delirious nights of sex, drugs, bebop and mambo and seraphic glimpses of truth and beauty. Like Fitzgerald’s Great Gatsby, which crystallised the glittering but directionless “lost generation” after the First World War, On the Road expresses both post-war exuberance and post-modern despair. It accepts the emptiness of existence but celebrates a search for higher truth, the unattainable “it” at the end of the road.

Kerouac inspired a wave of “beatnik” imitators and paved the way for the 1960s counterculture. The wide-ranging influence of On the Road can be seen in Ken Kesey’s One Flew Over the Cuckoo’s Nest, Fear and Loathing in Las Vegas by Hunter S Thompson and Gravity’s Rainbow by Thomas Pynchon. It lies behind Dennis Hopper’s 1969 film Easy Rider and it was a formative inspiration for a teenage David Bowie. “It changed my life,” said Bob Dylan, “like it changed everyone else’s.”

Following this extraordinary success, publishers became interested in Kerouac’s unpublished manuscripts, but he was hurt by the mixed response to his Buddhist novel, The Dharma Bums. Incessant press attention led to a worsening drink problem, and a feeling that he had to “get away to solitude again or die”, at which point the poet Lawrence Ferlinghetti – founder of the City Lights bookshop in San Francisco – offered Kerouac the use of his remote cabin on Big Sur, the rugged stretch of Californian coastline that runs between San Francisco and Los Angeles.

Kerouac made three trips to this cabin in 1960, where he wrote Big Sur, a raw account of his physical, emotional and creative breakdown. “I am a Breton!” he shouts at the Pacific Ocean, and from this time on he became increasingly obsessed by his French ancestry, chronicling a trip to Brittany in 1965 to research his family name in the novella Satori in Paris.

After a lifetime of heavy drinking, Kerouac died in 1969 at the age of 47. Several chapters of The Duluoz Legend remained unwritten, but he still left behind a “shelf full of books” that together form a wild and visionary self-portrait of a remarkable writer and human being, who would never have finished saying what he had to say.

“I’ve been reading and reading this gone Proust all the way across the country,” says Neal Cassady’s character at the end of On the Road, “and digging a great number of things I’ll never have TIME to tell you about”.

A centenary clothbound edition of ‘On the Road’ (Penguin Classics, £16.99) is out now. Henry Eliot presents the ‘On the Road with Penguin Classics’ podcast