Returning to the Road: The 60th anniversary of On the Road

“That’s not writing, that’s typing.”

Truman Capote’s famous dismissal of Jack Kerouac’s On the Road has been spat at me dozens of times. The book that, for a time in American history, defined “hip” is now a very uncool thing to like. To be fan of the book, as I am, is to come to terms with troublesome characters and cultural representation that hasn’t aged well. Perhaps, though, the book’s greatest sin is that it aims for profundity – and achieves it.

Today marks the 60th anniversary of the publication of Kerouac’s most famous literary work.

On the Road 1st Paperback Edition Cover (1958)

The story of Sal Paradise and Dean Moriarty is so ingrained in our cultural consciousness that any discussion of it almost feels like parody; but I’ll do it anyway. The thinly-veiled memoir-turned-novel tells of the aimless escapades of Kerouac and his friends from 1947 to 1950. The novel, which Kerouac famously typed on a single “scroll” of paper over three weeks while his then-wife fed him drugs, was published in 1957. The real story of the book’s creation, like the story itself, is lengthier and less sexy than the legend, but what difference does it make?

On the Road is one of the defining American myths, like Johnny Appleseed or George Washington’s cherry tree or Trickle Down Economics. Its veracity is less important than what it says about the culture that created it. As the United States is currently embroiled in startling regressive fights over nativism and isolationism, let’s remember that On the Road, more than almost any other book by an American author (certainly more than Capote) spoke to our nation’s historical roots as a nation of immigrants and wanderers.

There’s no escaping it: Sal Paradise, Dean Moriarty, and almost all of the other (male) characters in On the Road are loathsome people. They’re selfish and loutish, at times cruel, abusive towards the women in their lives, and ultimately wanton addicts that can barely stand themselves, let alone one another. In a word, On the Road is problematic.

So is history. So is art. So is life. I do not meant to wipe away the offenses of the characters or the real life people on whom they’re based, but rather to argue that there’s still a baby in that dirty bath water.

All art, especially historical works – and at 60-years-old, On the Road qualifies as an artifact – requires acknowledging flaws along with merits. Kerouac had questionable racial politics, no doubt, but for his time, the book’s sympathetic portrayal of the Hispanic immigrant populace was incredibly progressive. Frankly, it’s fairly progressive for our time. Despite all that Kerouac gets wrong in terms of cultural misappropriation and othering, he was at least willing to surmount walls to engage with different cultures.

Kerouac writes with considerable sympathy, especially for the cavalcade of degenerates that made up his beatnik circle. Dean Moriarty, in particular, was the quintessential anti-hero decades before such figures were the center of every TV show. There’s clearly a touch of Dean in Don Draper. The most common criticism I see lobbed at On the Road is that it glorifies these unlikeable characters as heroes. On the contrary, though, the desperate finale in Mexico is a denouement in the vein of Breaking Bad. We’re meant to live vicariously through these characters, but that doesn’t mean we’re meant to absolve them of all sins.

As far as Capote’s charges of “typing,” well, there’s really no accounting for taste. More than a few respected writers, both living and dead, have hailed Kerouac as an innovator and an influence, for what that’s worth. Kerouac’s breathless writing technique could certainly lead to paragraphs that feel aimless or empty, but there are also passages of pulsating beauty, exhilarating in their jazz-infused momentum and startling in their revelatory power.

For those who hate the book, for whom the characters are irredeemably repugnant and the writing is slapdash puffery, I make no effort to convince you otherwise. No, I’m writing for a different audience, for Kerouac’s audience, a crowd that has shrunk over the decades but that I suspect still exists in greater numbers than one might expect. It’s okay, you can come out of hiding.


Reading On the Road as a teenager should be transformative, the eye-opening experience when you realize that the world extends beyond your own yard and everyone’s life doesn’t have to follow a single path. For most readers, that philosophy resonates for a few years until they get a job or finish college with a stack of debt. Then, On the Road suddenly morphs into something far less profound, something childish.

Maybe you backpacked Europe or tried to make it as a musician for a few years. There might have been some poetry readings or even a Buddhist phase. Admit it: you were once idealistic. Don’t worry, I won’t tell anyone.

Grotesquely, the Beat Generation was long ago co-opted by corporate interests and sold as action figures and t-shirts, as is the fate for all forms of art and rebellion. There is no counterculture movement that can’t be neutered and decimated with a logo or a catchphrase. When a thousand drop-outs followed in Kerouac’s footsteps and hitchhiked across America, they were merely substituting one form of conformity for another.

The lesson of Kerouac’s travels is not that travel makes you free or that America is a nation of squares. What On the Road conveys is that we are all on a journey, that the perfect metaphor for life is the road, and ultimately, we alone are responsible for choosing – and reaching – our destination. Do with that what you will.

For me, that meant 10 Cities/10 Years: I took a decade out of my life to move across the country, meeting people from every corner of America and experiencing its wealth of stories. Diversity is a pleasure.

My copy

A year after finishing my project, I re-read On the Road for the first time since I was in college. I wondered – worried, really – that the book would have greatly diminished in the interim years, that adulthood would have dulled its potency.

Instead, I found that the book had evolved just as I had through my own journeys. No longer a guide to the unfettered thrill of escaping, the novel was a ledger for the costs and rewards of pursuing a dream. That was a life of travel for me, but it could be anything to anyone, the pursuit of any passion.

As you read this, I am currently embarking on a new travel journey, this time abroad. Though I’m eschewing a schedule like I had with 10 Cities/10 Years, the spirit that embodied that project remains. I will follow opportunities where they lead me. I will make my way as I always have, by working hard, saving money, and taking risks.

Before I departed, I’ll sold or gave away most of the few possessions I still owned. Things are a burden. I held onto a few essentials, though: Clothes, a laptop, old journals, and, of course, a dog-eared copy of On the Road.

One thought on “Returning to the Road: The 60th anniversary of On the Road

  1. I LOVE On the Road!
    I read it when I was 20, so 31 years ago; one of my highlights of turning 50 last year in Paris was seeing the ACTUAL typed manuscript of On the Road on display at an exhibition of 50s & 60s counter culture at Centre Pompidou. I even have a treasured photo, which I would love to post here but WordPress doesn’t have that facility 😐. I really enjoyed this honest post, thanks, gabrielle in Australia

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