In recent years, Jack Kerouac (1922-1969) and his Beat Generation writing has returned to the forefront of popular culture and counterculture (during the brief Hipster craze).

It’s no surprise his most famous book, On the Road (1957), keeps finding a young audience. As there’s a youthful verve behind his writing that’s timeless.

As long as you’re in your early 20s, read this work as a rite of passage and it’ll breathe possibility into your life. And that’s how we think it should be celebrated—as a celebration of youthful energy and positivity.

The Youthful Freedom and Self-Discovery of Kerouac’s On the Road

“Nothing behind me, everything ahead of me, as is ever so on the road.”

Kerouac had a famously intense writing style.

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

Kerouac 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 that’s a celebration of youthful hedonism, but one with tell-tale signs of the struggles the author would have in later life.

Steeped in Americana, the work has many dazzling tales during a pivotal moment in jazz history, freeloading (i.e. drinking), and wanderlust. It’s a romantic, riveting, and exhilarating account of what it is to be young and free-spirited.

“I realized these were all the snapshots which our children would look at someday with wonder, thinking their parents had lived smooth, well-ordered lives and got up in the morning to walk proudly on the sidewalks of life, never dreaming the raggedy madness and riot of our actual lives, our actual night, the hell of it, the senseless emptiness.”

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, and sense of adventure, the arrival of On the Road propelled him to fame.

On the Road’s Winding Narrative

“I woke up as the sun was reddening; and that was the one distinct time in my life, the strangest moment of all, when I didn’t know who I was – I was far away from home, haunted and tired with travel, in a cheap hotel room I’d never seen, hearing the hiss of steam outside, and the creak of the old wood of the hotel, and footsteps upstairs, and all the sad sounds, and I looked at the cracked high ceiling and really didn’t know who I was for about fifteen strange seconds. I wasn’t scared; I was just somebody else, some stranger, and my whole life was a haunted life, the life of a ghost.”

Taking up the alter-ego Sal Paradise, and Dean Moriarty for his maverick friend Neal Cassady (1926-1968), he spun a semi-autobiographical tale of travels 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 young man, Cassady’s endless energy, wit, intellect, and rambling shape the novel—Paradise is stunned by Moriarty and his lust for life.

That seems to be a forgotten edge to On the Road. That it’s really Moriarty who kind of drives the story, with Sal Paradise leaning back to enjoy the ride.

This book is like his journal report later to document the antics and remember the happy, silly days (to the backdrop of a jazzy number).

But Kerouac’s literary gifts are on full offer throughout. He had a real talent for writing, there’s no denying it. And although we think he improved on this work in his later books, this’ll always be the iconic one.

The book directly linked to his name forever. Especially with how On the Road 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.”

A brilliant piece of writing and one Kerouac narrated for the Steve Allen Show in 1959.

This appearance is something he references in his grittier work Big Sur (1962). A book that’s the hangover after his On the Road party.

And that is the sad element of looking at Kerouac’s most iconic work.

It launched him into a stardom he wasn’t prepared for. And one he didn’t enjoy. His celebrity exacerbated his drinking and it’d be the death of him before he even hit 50.

That’s something young readers to On the Road won’t care for. They’ll be in it for the journey. The fun and games.

But for older readers, especially ones reflecting on the work they may have read when they were younger, it’s also a cautionary tale. One of how hedonism is a lot of fun when you’re 20-something, but it must come to an end at some point.

Otherwise you’ll be out of here faster than Moriarty flooring it from the cops.

A Bit About On the Road’s 2012 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 quite the meandering affair which is brooding, moody, and features a host of very overenthusiastic characters drifting through life.

It does a decent job of capturing that sense of youthful excitement, but the characters do often come across as a bit annoying.

It’s enjoyable, plus beautifully shot, but we can recommend the book over the film.

Jack Kerouac’s Beat Generation Legacy

Whilst On the Road was (and still is) a celebration of youthful hedonism, it was also only published when Kerouac 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.

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.

He does capture the free-spirited nature of America in the ’40s.

His writing style used a stream of consciousness approach. He sat behind his typewriter and just went for it, using his natural sense of lyricism to structure the narrative laid out in his head.

Kerouac had a natural intelligence and this allowed his style to make for great stories. Although he was upset when critics shunned his approach to writing novels.

The suggestion being it was “easy” for him and took little effort, just taking three weeks to pelt out the latest Kerouac work.

It’s fair to say time has been kind to his beat generation canon.

Most of his works are still in print we should imagine future generations will still want to read about his madcap adventures. Like we put earlier, there’s a timeless quality here.

On the Road feels modern.

It isn’t. It’s over half a century old. But when accompanied by his other works, it depicts Kerouac’s life journey and the signs of a tragic early demise on the horizon.