An Illustrated Guide to Jack Kerouac’s On the Road, 60 Years Later

Illustrations © Nathan Gelgud

When I was a teenager, I owned the Penguin edition of On the Road, with the seafoam-color spine, and the black and white photo of Jack Kerouac and Neal Cassady on the cover. I’m not sure who recommended it to me or why I picked it up. But when I did, it did exactly what On the Road is supposed to do.

I dropped into Kerouac’s world with a crash. I loved everything about it. The cross-country driving with only a whisper of a plan and even less money. The love of jazz, the run-on sentences that made you feel like a book shouldn’t be telling you a story as much as tracing the contours of thought. Most of all, the friendships, and the game of figuring out who was who. And this was before the internet, so figuring all this out involved looking through Kerouac biographies and leafing through collections of beat literature, like The Portable Beat Reader.

on-the-road-full-comp-580The beat writers celebrated their influences, so learning about Kerouac and Allen Ginsberg meant learning about Thomas Wolfe, Jean Genet, William Blake, Louis-Ferdinand Celine, Walt Whitman. I never drove across the country, but On the Road sent me on a long trip through discovering some of my favorite books and poems.

But in the years since, I’ve become scared of On the Road. Surely the prose that I found so exuberant when I was younger would now feel bloated and indulgent, full of a forced, self-consciously hip argot and a childish need to call attention to its own style. Would it be possible to read On the Road and not cringe? If not at the writing itself, then at the memory of the naive high-schooler I was when I read it?

I need not have worried. It turns out that On the Road does not, as I’d remembered it, come off as a benzedrine-fueled stream of poetic reverie. To my surprise, it’s a novel with a structure and style that suit it perfectly. What’s more, it’s a surprisingly melancholy book. The narrator Sal Paradise has a feeling that “everything is dead,” and he can never quite shake it throughout the book, feeling himself and those around him to be ghosts. If there’s anything that was deeply unpleasant in reading it now, it’s not the writing style but the characters’ criminal treatment of women. But it’s certainly not unrealistic.

On the Road is a way into the literary heroes of the Beat Generation, but long stretches of the book that I’d forgotten about make up its best chapters. These parts don’t have anything to do with Kerouac’s poet and writer friends, but with his close-up look at poor and working Americans. The truck drivers who give him rides and the wanderers who he meets on his first trip west aren’t in search of kicks, but work. Sal himself gets a job as a security guard at a barracks, failing miserably at keeping the peace, and bums around the California coast with a young Mexican woman, considering spending the rest of his life doing migrant work. Twice, he gets disillusioned after journeying west, and makes cheap sandwiches to eat on the bus all the way back home.

It’s almost unfortunate that On the Road is so impactful to read as a teen, because it becomes just that: a book you read when you’re a kid. But its best, most deeply felt passages might only be appreciated by readers who’ve lived long enough to know what it really feels like to be beat.