information:classification, structural:reformatting
Later career: 1957–1969

In July 1957, Kerouac moved to a small house at 1418½ Clouser Avenue in the College Park section of Orlando, Florida, to await the release of On the Road. Weeks later, a review of the book by Gilbert Millstein appeared in The New York Times proclaiming Kerouac the voice of a new generation. Kerouac was hailed as a major American writer. His friendship with Allen Ginsberg, William S. Burroughs and Gregory Corso, among others, became a notorious representation of the Beat Generation. The term Beat Generation was invented by Kerouac during a conversation held with fellow novelist Herbert Huncke. Huncke used the term "beat" to describe a person with little money and few prospects. Kerouac's fame came as an unmanageable surge that would ultimately be his undoing.

Kerouac's novel is often described as the defining work of the post-World War II Beat Generation and Kerouac came to be called "the king of the beat generation," a term with which he never felt comfortable. He once observed, "I'm not a beatnik. I'm a Catholic", showing the reporter a painting of Pope Paul VI and saying, "You know who painted that? Me."

The success of On the Road brought Kerouac instant fame. His celebrity status brought publishers desiring unwanted manuscripts that were previously rejected before its publication. After nine months, he no longer felt safe in public. He was badly beaten by three men outside the San Remo Cafe at 189 Bleecker Street in New York City one night. Neal Cassady, possibly as a result of his new notoriety as the central character of the book, was set up and arrested for selling marijuana.

In response, Kerouac chronicled parts of his own experience with Buddhism, as well as some of his adventures with Gary Snyder and other San Francisco–area poets, in The Dharma Bums, set in California and Washington and published in 1958. It was written in Orlando between November 26 and December 7, 1957. To begin writing Dharma Bums, Kerouac typed onto a ten-foot length of teleprinter paper, to avoid interrupting his flow for paper changes, as he had done six years previously for On the Road.

Kerouac was demoralized by criticism of Dharma Bums from such respected figures in the American field of Buddhism as Zen teachers Ruth Fuller Sasaki and Alan Watts. He wrote to Snyder, referring to a meeting with D. T. Suzuki, that "even Suzuki was looking at me through slitted eyes as though I was a monstrous imposter." He passed up the opportunity to reunite with Snyder in California, and explained to Philip Whalen "I'd be ashamed to confront you and Gary now I've become so decadent and drunk and don't give a shit. I'm not a Buddhist any more." In further reaction to their criticism, he quoted part of Abe Green's café recitation, Thrasonical Yawning in the Abattoir of the Soul: "A gaping, rabid congregation, eager to bathe, are washed over by the Font of Euphoria, and bask like protozoans in the celebrated light."

Kerouac used earnings from On the Road to purchase the first of three homes in Northport, New York — a wood-framed Victorian on Gilbert Street that he shared with his mother, Gabrielle. They moved there in March 1958 and stayed in Northport for six years, moving twice during that time.

Kerouac also wrote and narrated a beat movie titled Pull My Daisy (1959), directed by Robert Frank and Alfred Leslie. It starred poets Allen Ginsberg and Gregory Corso, musician David Amram and painter Larry Rivers among others. Originally to be called The Beat Generation, the title was changed at the last moment when MGM released a film by the same name in July 1959 that sensationalized beatnik culture.

The television series Route 66 (1960–1964), featuring two untethered young men "on the road" in a Corvette seeking adventure and fueling their travels by apparently plentiful temporary jobs in the various U.S. locales framing the anthology-styled stories, gave the impression of being a commercially sanitized misappropriation of Kerouac's story model for On the Road. Even the leads, Buz and Todd, bore a resemblance to the dark, athletic Kerouac and the blonde Cassady/Moriarty, respectively. Kerouac felt he'd been conspicuously ripped off by Route 66 creator Stirling Silliphant and sought to sue him, CBS, the Screen Gems TV production company, and sponsor Chevrolet, but was somehow counseled against proceeding with what looked like a very potent cause of action.

John Antonelli's 1985 documentary Kerouac, the Movie begins and ends with footage of Kerouac reading from On the Road and Visions of Cody on The Steve Allen Show in November 1959. In response to Allen's question "How would you define the word 'beat? ' ", Kerouac responds "well... sympathetic."

In 1965, he met the poet Youenn Gwernig who was a Breton American like him in New York, and they became friends. Gwernig used to translate his Breton language poems into English so that Kerouac could read and understand them : "Meeting with Jack Kerouac in 1965, for instance, was a decisive turn. Since he could not speak Breton he asked me: 'Would you not write some of your poems in English? I'd really like to read them !... ' So I wrote an Diri Dir – Stairs of Steel for him, and kept on doing so. That's why I often write my poems in Breton, French and English."

During these years, Kerouac suffered the loss of his older sister to a heart attack in 1964 and his mother suffered a paralyzing stroke in 1966. Kerouac moved in with his mother in Hyannis, Massachusetts, for almost a year in 1966. In 1968, Neal Cassady also died while in Mexico.

Despite the role which his literary work played in inspiring the counterculture movement of the 1960s, Kerouac was openly critical of it. Arguments over the movement, which Kerouac believed was only an excuse to be "spiteful," also resulted in him splitting with Ginsberg by 1968.

Also in 1968, Kerouac last appeared on television, for Firing Line, produced and hosted by William F. Buckley Jr. (a friend of his from college). Seemingly intoxicated, he affirmed his Catholicism and talked about the counterculture of the 1960s.