Jack Kerouac would have been a hundred years old today. In the end, he didn’t come close to that milestone. He didn’t even live half that long. Despite his many healthy incarnations — capable student, star sportsman, free spirit, Buddhist disciple — he was constantly plagued by inner demons. Always a heavy drinker, he spent his last years hooked on and ravaged by booze, alongside Benzedrine, cigarettes and goofballs. As his biographer Gerald Nicosia put it, Kerouac was “lushing himself to the grave, and using whatever drugs he could get to soar with the angels before he got there.” That grave was an early one. He died in 1969, aged 47.

Kerouac left behind a number of books, the most famous — though not necessarily the best — being On the Road (1957). To chime with his centenary, Penguin has just published an anniversary edition in its Clothbound Classics range. It seems odd for the so-called Bible of the Beat Generation to be available as a pristine hardback, complete with prettily patterned cover, coloured endpapers and integrated silk ribbon bookmark. On the Road shouldn’t stand stiffly on a bookshelf. It is a portable paperback, one which you stuff in pockets or stash in glove compartments and allow to get battered, tattered and dog-eared on a mind-broadening journey of self-discovery. 

Still, the new edition is a beautiful thing and serves as a reminder that Kerouac’s art has endured. Those who begin with his seminal novel then venture beyond it to sample the other novels in his oeuvre quickly realise that they are all loosely linked. Collectively, they constitute a memoir cycle called “The Duluoz Legend”. 

With his new bohemian cohorts Kerouac sloughed off an old skin

Kerouac first envisaged the project during the war when he was a 21-year-old merchant sailor. In his 1968 novel Vanity of Duluoz, his alter-ego Jack Duluoz looks back on his time at sea and remembers how reading John Galsworthy’s The Forsyte Saga in his bunk gave him the idea of “novels connecting into one grand tale.” Then on a grey drizzly morning while on shore leave in Liverpool he sits at a typewriter in the purser’s office and visualises “a lifetime of writing about what I’d seen with my own eyes” coming together and forming “a contemporary history record”. 

So far, so In Search of Lost Time. But in his introductory note to Big Sur (1962), Kerouac outlined a marked difference to his approach: “My work comprises one vast book like Proust’s except that my remembrances were written on the run instead of afterwards in a sick bed.” Being on the road and on the run enabled Kerouac to live fast, test limits, cross boundaries and then chart every raw emotion and gritty experience in his candid autobiographical fiction. Delving into it, we get a valuable portrait of a flawed man navigating his way through, what he termed, a world of “raging action and folly and also of gentle sweetness.”

Kerouac was born in Lowell, Massachusetts, in 1922, to working-class immigrant French-Canadian parents. Three of his novels cover key chapters from his formative years. Visions of Gerard (1963) is composed of a series of recollections of his older brother who died of rheumatic fever at the age of nine in 1926. Part meditation on the joys of childhood, part chronicle of a death foretold, the book is one of Kerouac’s most affecting. Maggie Cassidy (1959) is a tale of first love based on Kerouac’s teenage romance with sweetheart Mary Charney, while Vanity of Duluoz traces his “adventurous education” and exploits at both high school and Columbia University. 

It was on and around the Columbia campus in the summer of 1944 that Kerouac met and cemented friendships with Lucien Carr, Allen Ginsberg and William Burroughs. All four were among the founding fathers of the group Kerouac later called “Beat” — short not for deadbeat or downbeat but beatific. With his new bohemian cohorts Kerouac sloughed off an old skin and embarked on a radical new way of living, one fuelled by drugs and defined by artistic experimentation and rejection of social conventions.

Those fellow charter members of the Beat Generation altered his outlook and went on to play a crucial role in his life — so much so that they crop up regularly as characters in his work. However, the one person Kerouac truly clicked with, and even looked up to, was Neal Cassady. Kerouac’s “blood brother” became his travelling companion on several cross-country trips plus a further expedition south of the border. Kerouac drew on those experiences for On the Road, turning Cassady into the equally charismatic rebel Dean Moriarty and their journeys across “that awful continent” a quest for freedom and fulfilment. 

Kerouac knocked out his “road book” in three weeks on a 120-foot-long, single-spaced typed scroll. Benzedrine kept him awake; a succession of “after-dinner black coffees” kept him going. The New York Times hailed its publication in 1957 as “a historic occasion insofar as the exposure of an authentic work of art is of any great moment in any age.”

Kerouac is at his most compelling in print when he is off the road

That same year, Kerouac recorded more of his travels in The Dharma Bums. Along with accounts of hitching rides and hopping freights is his fictionalised depiction of a trek he made with friends to scale the summit of Matterhorn Peak in the Sierra Nevada. His characters’ goal is spiritual enlightenment — something that is hard to come by back in “Frisco”, where they lose themselves in boozy poetry readings, riotous three-day parties and “a simple healthy orgy”. 

The Dharma Bums and On the Road inspired millions to criss-cross America in the sixties and they remain Kerouac’s most popular works. 

But for my money Kerouac is at his most compelling in print when he is off the road and off the rails. He first offered glimpses of his darkening soul and troubled mind in The Subterraneans (1958). Written over three feverish days and nights, the book is a dramatisation of Kerouac’s short but intense love affair with Alene Lee, someone his fictional counterpart describes as “one of the most enwomaned women I’ve seen, a brunette of eternity incomprehensibly beautiful”. Kerouac’s character, a self-proclaimed egomaniac, props up bars in San Francisco, spirals out of control, and realises he is afraid to get in too deep. At the end he takes stock of his woeful situation: “deep in the dark pit of night under the stars of the world you are lost, poor, no one cares, and now you threw away a little woman’s love because you wanted another drink with a rowdy fiend from the other side of your insanity.”

Tristessa (1960) tells of another of Kerouac’s ill-fated relationships, this time with a prostitute and morphine addict in Mexico City. Kerouac’s stand-in hangs out with her in her squalid “cell-house” full of animals and drinks super-strength Juarez Bourbon to help him “crash through the black curtain”. When oblivion proves unattainable, he heads out and stumbles drunkenly around in the rain, going nowhere fast and searching in vain for ways to save “junk-racked” Tristessa but also himself.

By the time we get to Big Sur, Kerouac’s protagonist is starting to resemble a lost cause. The novel — arguably the most powerful instalment in The Duluoz Legend — recreates several weeks in California in the summer of 1960 when Kerouac went far from the madding crowd of critics, fans and reporters for solitude and sobriety in a “cabin of sweet loneness”.  Unfortunately, the solitude proved too much and the sobriety didn’t last. 

Kerouac told friends this book, a “narrative drama”, was “honester” than his others. Indeed, its pages are thick with graphic descriptions of marathon drinking sprees, gruelling hangovers, bouts of self-loathing and mental breakdown, all of which make for sobering reading. This marked the beginning of the end; it was a foretaste of what little future Kerouac had left. Still, it is miraculous that he was able to produce one of the high points of his career at one of the lowest ebbs in his life.

Not all of Kerouac’s literary output was as satisfying. Some of it is for diehard Kerouacolytes only. Satori in Paris (1966), which recounts a trip he made to France to trace his heritage while in an alcoholic haze, is a damp squib after previous pyrotechnics. And the posthumous Visions of Cody (1972) is a long, tedious, convoluted mess — or to borrow a handy phrase from Vanity of Duluoz, “hullaballoo boomboom horseshit”. At times it is all too easy to side with Truman Capote and mock Kerouac’s technique of “spontaneous prose”. “That’s not writing,” Capote scoffed, “it’s typing.”

And yet, Kerouac’s “kickwriting” can be truly exhilarating. He bombards us with warped logic, skewed syntax and wonky grammar. He throws us with strange descriptions (“the lickety ticky moon”, “the Ma-Wink fallopian virgin warm stars”), out-there comparisons (“like a constipated angel on a cloud”), steady supplies of concocted words (“bewrongled”, “befawdledawdled”) and Joycean gibberish (“wild dark Lowell so swallowed me doom its croign of holobaws”). 

In the end it pays not to ask too many questions and instead just accept the chaos, submit to the rhythms and go with the freewheeling flow. By doing so we get to know all manner of characters — bohos and hobos, hipsters and hustlers, hepcats and beatniks, loners and dreamers, Dharma bums and desolation angels. More importantly, though, we get to come up close and personal with Kerouac. Like his protagonist in The Subterraneans, he “let the truth seep out”. In the best of his books, we share his thrills and we feel his pain.