Road trip

King of the road

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Road trip

The inspiration for Jack Kerouac’s influential novel On The Road, Neal Cassady was part-hustler, part-bohemian, remembers Roger Crosthwaite.

Jack Kerouac’s cross-country coming of age novel On The Road has inspired millions of young people around the world to leave their safe, suburban cocoons and take to the highways in search of something—the truth, “America”, their own selves, or maybe just a good time.

While On The Road’s narrator, Sal Paradise, was obviously just a thinly disguised Kerouac, the book’s real hero and centrepiece, Dean Moriarty, seemed too larger-than-life, too crazy, too extravagant to be true.

Jack Kerouac On The Road


The truth is that Neal Cassady, the inspiration for Moriarty, was bigger and crazier than anything in the pages of a book.

If anyone’s to blame for all those thousands of starry-eyed, road-tripping truth-seekers clogging up truckstops trying to cadge lifts, its Neal Cassady.

The son of an alcoholic barber, Cassady grew up on the streets and in the flophouses of Denver, Colorado, combining his two passions stealing cars and reading everything he could lay his hands on.

By the age of 15, with an impressive juvenile criminal record and an off-the-charts IQ, he was taken under the wing of Denver intellectual I.W. Briefly, who set about educating the young street tough, enrolling him in school and introducing him to philosophers such as Proust and Schopenhauer.

But Cassady wasn’t about to take the easy route offered. His light-fingered love for cars he could never afford led to jail time, after which, at the age of 18, he married a stunning 15-year-old blonde named LuAnne in 1945, kicked the Denver dust off his shoes and headed for New York.

There he fell in with a crowd of prototype beatniks horn Columbia University that included Kerouac and poet Allan Ginsberg. In the company of Kerouac, Cassady enacted the crazed, amphetamine-fuelled criss-crossings of the USA that became the base material for On The Road.

Discarding and acquiring wives, lovers, jobs, friends and philosophies at a blistering pace, Cassady seemed to live a couple of time zones ahead of everyone else. His speed-fuelled raps were legendary. Long-time friend Paul Foster described conversation with Cassady as “voluminous, humorous, often rhyming and intimidatingly encyclopaedic… he could handle eight different channels of audio interchange, including items from all the radios and TVs he had turned on, random street noise, all conversations within earshot and several secret thoughts?’

While his friends—and rumoured lovers—Kerouac and Ginsberg became published authors and noted literary figures, Cassady’s own life spiralled downward. He worked a series of dead-end jobs, including a couple of years as a railway conductor, embarked on more marriages (becoming a bigamist in the process), and served two years in San Quentin after offering an undercover cop a joint.

But in the early 1960s, with the Beatnik era fading and a new pulsing light on America’s counter-cultural horizon, Cassady had a rebirth of sorts.

Identifying strongly with Randall McMurphy, the hero of Ken Kesey’s novel One Flew Over the Cuckoo’s Nest, he showed up at Kesey’s house near San Francisco and insinuated his way into the crowd of Stamford University intellectuals them.

Kesey’s “Acid Tests” —group experiments with the then-legal drug LSD—were just what Cassady needed to re-fire his boilers. He became the official driver for Kesey and his troupe, dubbed the Merry Pranksters, when they embarked on their infamous 1964 cross-country trip in a psychedelic painted school bus with a destination sign reading “Furthur”.

Young hippies who had grown up on On the Road and Dean Moriarty were amazed to find the real deal in their midst.

But as the 1960s were on, Cassady’s tank was near empty, physically and psychically battered by 20-plus years of near constant amphetamine use, jail and his on-going marital complications.

After one last lightning-flash, coast-to-coast driving tour of the USA in 1968, he wound up in San Miguel de Allende, Mexico, where, after attending a party, he passed out on the railway tracks and died of exposure.

He wasn’t quite 42 years old. It had been a long and crazy trip, but he was at the and of the road

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