On The Road is the defining novel of the 1950's Beat Generation.
It's spontaneous prose mirrors the free-spirited counter-culture it describes.
I was surprised to learn the author was living in the suburbs of Florida with his mother in a defeated state of self-exile...
The author, Jack Kerouac, did go on four epic road trips between 1947-50.
On the Road romanticizes hitchhiking, casual sex, drugs, non-conformity; all rendered in loose ecstatic writing.
While the book turned Kerouac into a legend, the author's real life was way more nuanced.
Our image of Kerouac is over-indexed on 'the hitchhiker.'
In reality he:
- Yearned for the stability of home life
- Was shaped by a Catholic upbringing
- Intensely studied religion and writing
And while writers see him as lazy and undisciplined, he was actually studious.
Before Kerouac's road trips, he wrote over 1 million words in traditional prose in the 1940s.
Kerouac dreamed of writing "The Great American Novel," and studied classic poets and writers like Whitman, Melville, and Wolfe.
His experimental prose can be traced back to one friend.
NYC. 1946. Kerouac meets Neal Cassady.
While Kerouac was (relatively) introverted, Cassady was wild (he was the psycho bus-driver in The Electric Kool-Aid Acid Test).
Cassady had a restless, adventurous energy that Kerouac thought would make a great story.
They went on 4 cross-country trips together.
Kerouac captured Cassady's unrestrained lifestyle in the character "Dean Moriarty," making him the muse for both the Beat and hippy generations.
While Cassady influenced Kerouac's philosophy, he had a bigger impact on his craft.
1950, in the winter after their last road trip, Cassady sends Kerouac the "Joan Anderson Letter."
It was "the best piece of writing he's ever seen" (13,000 words, 40 pages on a 3-day benzedrine-binge)
Spontaneous prose was born.
Kerouac thought: imagine a whole book like this?
1951. Kerouac is ready.
He had road journals, old drafts, marked up maps, a decade of practice, and now an new vision around prose and process from Cassady.
In 20 days, he huffs out On the Road in 1 take, without paragraph breaks, on a 120 foot scroll.
Was it any good?
The consensus from his rejection letters was: "enormous talent, but unmarketable."
At a subject level, it was a culture shock to conservative ethics.
At a style level, he refused to edit anything.
Between 1951-53 he wrote more radical novels among radical friends.
No takers.
By 1954, Kerouac was exhausted. Cassady's lifestyle wasn't sustainable, and his inability to get published was existential.
After reading Thoreau, he retreated into nature. For 3 years, he studied Buddhism, and wrote books on sorrow, solitude, and mysticism.
This new phase peaked in 1956, when he spent 63 days on Desolation Peak in full isolation.
Kerouac dreamed of being a hermit. This comes from his Catholic roots and his brother's vision of the Virgin Mary before his death. For once, Kerouac had solitude.
Turns out, he hated it.
It was the end of road.
Neither the vagabond or monkish lifestyle worked out, and in July of 1956, he moved to a small 2-room house in Orlando, Florida with his mother.
None of his books were published.
At his lowest point, his career took off.
Two months after Kerouac moved to Florida, the poem "Howl" goes viral. Written by his friend Allen Ginsberg, it's both popular and controversial.
It brings light to the "Beat movement," and suddenly, publishers see an urgent opportunity to publish Kerouac's work.
After years of frustration and resistance, Kerouac finally agrees to have his original scroll of On the Road edited.
This was led by editor Malcolm Cowley who gives it a linear structure, adds chapter breaks, and tones down the obscenity.
How was it received?
The NY Times was the 1st to give it attention.
It was a "historic occasion" & “the most beautifully executed, the clearest and the most important utterance yet made by the [Beats]"
Kerouac became the 1st "writer celebrity of the TV age."
But the public's reaction tortured him.
Intellectuals scorned him, and the youth worshipped him for a failed lifestyle experiment from 10 years ago that he since outgrew.
While Cassady was the actual embodiment of "the Beat," Kerouac got all the unwanted fame and flack.
After his rise, did he continue writing?
Kerouac was an introvert, and attention destroyed him.
"No time to think, no time to write."
After his fame, all his earlier books got published, but his writing dried up and got dark.
He denounced his friends and drank himself to death at 47 years old.
Kerouac's tale was a tragic one.
His public image was distorted.
His philosophy was misunderstood.
His life was tortured by alcoholism.
And his craft (the thing he cared about most) was written off as rambling.
Is he sometimes long-winded? Yes.
Could his books have been better if he was more open to editing? Sure.
But if you're patient, he does break through with some unbelievable prose-poetry (like this sentence from Dharma Bums).
I'm on a quest to read Kerouac, wade through it all, pick out the best parts, and break them down.
Follow me here on Twitter if you want to see sentences & paragraphs from Kerouac (and others) visually deconstructed.