Jack Kerouac (1922-1969) and his Beat Generation writing has returned to the forefront of literature, counterculture, and popular culture in recent years.

On the Road is his most famous book, with the likes of feature films and documentaries championed by the likes of Russell Brand. And the Hipster movement is also latching onto his work like deranged hippies tripping on acid.

It’s all propelled a man who has been dead for almost 50 years back into the limelight.

On the Road

He penned notes for the novel in the late ’40s and then, famously, over three weeks in April 1951, he thrashed On the Road out day and night whilst slumped over his typewriter.

He even stuck the sheets of paper together so he wouldn’t have to interrupt his stream of consciousness style of writing. The result? A magnificent book which is a celebration of youthful hedonism, but one which would ultimately backfire on its author.

Steeped in Americana, accounts of a pivotal moment in jazz history, freeloading (i.e. drinking), and wanderlust, On the Road is a romantic, whimsical, riveting, and exhilarating account of what it is to be young and free-spirited.

It’s no wonder successive generations have found it so compelling – throw off the shackles of your dreary 9-5 job and hit the beaten track with only your jeans, a dream, and youthful good looks! Romantic, or what?

Good looks is something Kerouac had in spades – “more beautiful than Marlon Brando” was how he was once described. With his natural intelligence, lyrical voice, charisma, sense of fun, and sense of adventure, the arrival of On the Road immediately propelled him to fame.

Taking up the alter-ego Sal Paradise for his story, and Dean Moriarty for his maverick friend Neal Cassady, he spun a largely autobiographical tale of hedonism and travel across America.

Whilst the joys of exploration on the open road is at the forefront, it’s Kerouac’s friend Cassady, whom the writer was so in awe of, who takes centre stage.

Evidently, a most charismatic man, his endless energy, wit, intellect, and rambling nature shape the novel – Paradise is, simply put, stunned by Moriarty and his lust for life.

On the Road, which we believe everyone should give a whirl to experience its freewheeling and energetic nature, even closes with this ravishing segment:

"So in America when the sun goes down and I sit on the old broken-down river pier watching the long, long skies over New Jersey and sense all that raw land that rolls in one unbelievable huge bulge over to the West Coast, and all that road going, and all the people dreaming in the immensity of it, and in Iowa I know by now the children must be crying in the land where they let the children cry, and tonight the stars'll be out, and don't you know that God is Pooh Bear? the evening star must be drooping and shedding her sparkler dims on the prairie, which is just before the coming of complete night that blesses the earth, darkens all the rivers, cups the peaks and folds the final shore in, and nobody, nobody knows what's going to happen to anybody besides the forlorn rags of growing old, I think of Dean Moriarty, I even think of Old Dean Moriarty the father we never found, I think of Dean Moriarty."

Film Adaptation

You can watch the film, if you want. Maybe strap on some skinny jeans, a grandad jumper, and light your pipe as the opening credits roll – it’s arguably the most Hipster-friendly film of all time.

Starring Sam Riley and Kristen Stewart, it’s a meandering affair which is brooding, moody, and features a host of incessantly overenthusiastic (i.e. annoying) characters drifting through life. It’s passably enjoyable, plus beautifully shot, but read the book instead.

Kerouac’s Legacy

Whilst On the Road was (and still is) a celebration of youthful hedonism, it was also only published when he was fast approaching middle age. Such was the difficulty he had in reaching that stage in his career.

Consequently, when it became a hit and shot him to stardom, Kerouac was suddenly besieged by a small army of teenagers and students turning up on his doorstep expecting to party with the, no longer, 20 something writer. Big Sur documents some of this

Kerouac had inadvertently stylised himself as the perpetually young reveller who travelled about hitchhiking. This practice is pretty much illegal these days and never was a thing in the UK – try that in England and you’ll just get ignored.

On the Road isn’t set in England, though, it’s in America – the land of the free, where shotgun wielding extroverts hang loose at every corner (this is our, probably dimwitted, understanding of life in the US).

Sadly, the media and public attention for the introverted Kerouac was all too much, as with the trappings of fame he felt as if he had to live up to his hedonistic image. Much of this is detailed in his candid work Big Sur.

To deal with his persistent fans and a spiralling circle of sociable expectations, he drank heavily for his entire adult life until it caught up with him in 1969, leading to his shockingly sudden demise.