I started reading Jack Kerouac’s On the Road the day after graduating college. I’d always known about the novel, but what really drew me in was a quote from actor Nick Nolte. He once said that On the Road had profoundly shaped his life.
While I wouldn’t say I idolize Nolte, that kind of endorsement made me curious. And like many timeless books, it did end up shaping me—especially in my twenties. I highly recommend it to recent grads or anyone about to start something new.
Just three weeks after finishing the book, I moved to Aspen. I had never even been to Colorado.
The Beat Generation’s Defining Book
Published in 1957, On the Road is often considered the defining novel of the Beat Generation. This movement emerged after World War II and was rooted in rebellion, spontaneity, and nonconformity.
Kerouac’s prose captured that spirit. Inspired by jazz, he wrote in long, flowing sentences meant to mimic improvisation. He even delivered the first draft as one continuous scroll—no chapters, no paragraphs. Thankfully, the published version was more readable.
I’ve tried reading the original scroll version. I don’t recommend it.
A Journey to Identity and Freedom
At its heart, On the Road is about searching for identity. Sal Paradise (Kerouac himself) travels across the country to find meaning. Along the way, he meets a cast of unforgettable characters.
He writes about fellow Beat icons like William Burroughs, who penned Junky, and Allen Ginsberg, the poet behind Howl. Sal’s best friend, Dean Moriarty (based on Neal Cassady), later became the driver of the famous bus Further during Ken Kesey’s Merry Prankster trip—immortalized in The Electric Kool-Aid Acid Test by Tom Wolfe.
A Cultural Legacy That Still Moves
The cultural impact of On the Road can’t be overstated. It helped shape the counterculture of the 1960s, inspiring people to question norms and embrace exploration.
The book made road trips and cross-country travel a symbol of freedom. That legacy lives on in literature, film, music, and even advertising. And its influence will keep inspiring new generations of wanderers.
Want to read the book?