The Fact and Fiction of Jack Kerouac's On the Road

If you are so much as a leisurely fan of American fiction, you likely already know the story of how On the Road came into the world—how, in April 1951, the novel spewed forth from Jack Kerouac in an almost magical reverie that lasted a full three weeks of days and nights in a Chelsea loft, as he wrote without pause on a 120-foot-long scroll. Likely fueled by Benzedrine—although he claimed to have taken in nothing stronger than coffee—Kerouac wrote the novel as fast as he could think it, and in doing so defined a generation and helped solidify a nation’s love affair with the road trip. Few events in literary history have captured the public imagination with such force.

As a casual reader of Kerouac’s work, this was my understanding of On the Road, as well, when I began research on my book, Process: The Writing Lives of Great Authors, in 2013. That year I was granted access to the Berg Collection in the New York Public Library, where some of the English language’s most important archives are housed, including Kerouac’s.

At the end of a hushed hallway on the third floor of that imposing building on Fifth Avenue, I’d ring a bell and wait to be let in. Once inside, I’d present my credentials and turn over my belongings, then let the librarian know which documents I wanted to view. On one visit, I requested certain of Kerouac’s journals, then sat and waited in this, the quietest room in New York City. After a few minutes, a folder was placed in front of me. To my astonishment, opening it brought me face to face with a handwritten draft of On the Road written the year before Kerouac wrote the famous scroll version.

I would go on to examine not only this one draft of On the Road, but several. By the count of Berg Collection curator Isaac Gewitz (whose book Beatific Soul: Jack Kerouac’s On the Road was a great aid in researching this article), at least a half-dozen “proto-versions” of Kerouac’s famous novel exist, all written in the three years preceding the apparently spontaneous composition of the novel on a single scroll.

The true story of On the Road, then, is this: In 1947, while still working on his first novel, The Town and the City, Kerouac decided to next write a novel about the American road. In the following years, he would traverse America several times in service of that project. The first explicit reference to On the Road came in August 1948, when Kerouac referred to the novel by name in his journal: “I have another novel in mind—‘On the Road’—which I keep thinking about: two guys hitchhiking to California in search of something they don’t really find, and losing themselves on the road, coming all the way back hopeful of something else.”

The first draft came a few months later, with a protagonist named Ray Smith who is clearly based on Kerouac and undertakes a road trip similar to the one near the beginning of the published On the Road. (Ray Smith would also be the name of the Kerouac character in The Dharma Bums.) In this initial version, Kerouac’s travel buddy is more strongly based on fellow Beat Lucien Carr than on Neal Cassady, the eventual model for Dean Moriarty.

Kerouac embarked on another cross-country trip in 1949, and this time kept a journal where he recorded his ideas for the novel—passages from which made their way in slightly revised form into the scroll manuscript. He also worked out the plot during this time, and by November 1949, had an outline of the novel in place.

The story itself was coming together. But early versions of On the Road reveal an author still struggling to find a style and a temperament that fits the novel he wants to write. He had yet to abandon formal, sentimental narrative, or even switch to the first person from the third. These drafts differed starkly from the published novel in their style, with more conventional structures and a lot of rote historical context for the America he wanted to capture. A typescript draft from 1950, for example, opens with a historical account of the American West, “presented to mankind for the first and last time in its grand natural form of plains, mountains and deserts beyond a great river when the continent of the United States extending from one ocean to another, from East to West, from one side of the world to the other, was discovered and settled by the first embattled arrivers.” He goes on to catalog the roads that grew to traverse the continent—Route 6, Route 50, Route 66, Route 40, and so on—before introducing any plot points or characters. The ideas were there, but the form remained awkward.

“I’ve been grinding & grinding my mind on The Road idea for years now…” Kerouac wrote with some frustration in his journal on February 18, 1950. Around this time, he finally started to truly experiment with form. In another draft from October 1950, this one handwritten, Kerouac structured the story as a newspaper called The American Times. It opens with an article titled “On the Road: The Night of September 27,” in which a young Kerouac-like character takes off on a journey across America from his hometown of Lowell, Massachusetts (also Kerouac’s hometown). In early 1951, he wrote the last pre-scroll draft of the novel—this one was written in French, Kerouac’s first language, which he’d spoken at home with his French-Canadian parents. These versions share little stylistically with the final novel, but they show that Kerouac was now grasping for a distinctive voice.

The key event in his finding that voice came in December of 1950, when Kerouac received a long, feverishly written letter from Neal Cassady recounting a bender of a weekend he’d had recently in Denver. Kerouac found himself besotted by the impulsive, freeform tenor of the letter and used it to develop a new approach to writing, which he famously dubbed “spontaneous prose.” Kerouac later told The Paris Review that the letter was “the greatest piece of writing I ever saw,” and it gave him what he called the “flash” he’d been looking for in his own writing. (Though it was long thought lost—Allen Ginsberg claimed a fellow poet had lost it in San Francisco Bay—Cassady's “Joan Anderson Letter” was rediscovered in a pile of "to read" mail in 2012, then put up for auction by Christie's in 2016. It sold for $380,000.)

By the spring of 1951, Kerouac had solidified his writing style and amassed hundreds of pages of notes for the novel, in which he pondered the purpose of his book and how it related to the Beats, fleshed out his characters, and took down anecdotes. Some of this content made its way directly into the scroll draft, and then into the published novel. A draft from 1950, for example, opens with a version of what would eventually become the final paragraph of the published On the Road. Another 13-page draft from that year, titled “Flower that Blows in the Night,” includes one of the classic scenes from On the Road, in which Sal Paradise and Dean Moriarty go listen to jazz in a San Francisco club.

When he sat down in April 1951 to type the scroll manuscript, Kerouac had on the table beside the typewriter a list of reference points for himself—events, descriptions, and themes that served as writing prompts over the following weeks: “Talk about Neal with Hal,” “Idiot girl—atombomb Turkey, box of salt, blue lights,” “Neal and I in yard ... of Chrysler man,” etc.

Then, he wrote more than 120,000 words in three weeks. It was a fantastic performance, but it wasn’t unrehearsed, and can in fact be more accurately understood as the culmination of at least three years of work. It would be six discouraging years and several more revisions before it saw publication—10 years total from conception to publication. Despite its place in literary history as a miraculous feat of imagination and endurance, Jack Kerouac’s plight in writing On the Road just may represent the loosest-ever definition of “spontaneous.”