Jack Kerouac was not a happy man in 1969. It had been a dozen years since his novel On the Road had been published to much acclaim and excitement. The era of the Beats had passed into that of the hippies. His old friends Allen Ginsburg, William Burroughs, and Neal Cassady joined in the next-generational fun, but Kerouac told interviewer Ted Berrigan, “I don’t know one hippie anyhow….I think they think I’m a truck driver.”

He didn’t like hippies, even as he bragged of “having smoked more grass than anyone you ever knew in your life.” He proclaimed himself “pro-American,” a supporter of the war in Vietnam, while Burroughs and Ginsberg and company were “very socialistically minded.” Yet Howl and Naked Lunch sold and sold while Kerouac was left to lament the poor reception of his novels Satori in Paris and Vanity of Duluoz even as he hoped that “earlier readers would come back and see what 10 years had done to my life and thinking.” For the most part, they didn’t. In the first half of 1969, Kerouac told a later interviewer, he had made only $1,770 in royalties, the equivalent of about $12,750 today. Granted, he allowed, he had added $3,000 to the trove that summer with a syndicated op-ed piece about “the Communist conspiracy.”

His cohort had split up at the beginning of the ’60s, Kerouac said, each going his own way. He added, “And this is my way: home life, as in the beginning, with a little toot once in a while in local bars.” “Home life” meant living with his elderly, paralyzed mother in a small house in downtown St. Petersburg, Florida, which He Called “A Good Place To Come Die.” A “little toot” meant sitting in a chair in the living room with a constantly replenished glass of whiskey and a flow of beer, watching television. “Once in a while” meant showing up at a couple of bars down the street at opening time and arguing about politics for a few hours. His wife, Stella, who shared his mother’s house, called him “a very lonely man.”

He got into a fistfight at one such tavern in the late summer of 1969, and it didn’t go well for him. He had been speaking in a stereotyped version of Southern African American speech— the same kind of speech he employed in his posthumously published novel Pic—when he was beaten, patrons reported. Though sympathetic to the racial injustices a young man faced in the South, the novel was not well liked, and it soon went out of print. A few weeks after the fight, on Oct. 21, 1969, Jack Kerouac died of cirrhosis of the liver. He was 47 years old.

Kerouac had better fortune posthumously. Late in 1975, Allen Ginsberg and Bob Dylan visited his grave and, Ginsberg wrote, “traded lines improvising a song to Kerouac underground beneath grass and stone.” The visit anticipated the widespread rediscovery of Kerouac’s work, particularly On the Road, which has never been out of print since, now half a century after its author’s passing.

Gregory McNamee is a contributing editor.