Originally published in 1965, this autobiographical novel covers a key year in Jack Kerouac’s life—the period that led up to the publication of On the Road in September of 1957. After spending two months in the summer of 1956 as a fire lookout on Desolation Peak in the North Cascade Mountains of Washington, Kerouac’s fictional self Jack Duluoz comes down from the isolated mountains to the wild excitement of the bars, jazz clubs, and parties of San Francisco, before traveling on to Mexico City, New York, Tangiers, Paris, and London.

Written over the course of three days and three nights, The Subterraneans was generated out of the same kind of ecstatic flash of inspiration that produced another one of Kerouac’s early classics, On the Road. Centering around the tempestuous romance and breakup of Leo Percepied and Mardou Fox—two denizens of the 1950s San Francisco underground—The Subterraneans is a tale of dark alleys and smoky rooms, of artists, visionaries, and adventurers existing outside mainstream America’s field of vision.

A long poem in Kerouac’s freewheeling and spontaneous improvisational style, Mexico City Blues is a unique epic of sound, rhythm, and religion. Called superb sensory meditations, the poetry takes in life, death, and spirituality but roams widely across continents and cultures. Memories, fantasies, dreams, and surrealistic free association are all lyrically combined in the loose format inspired by jazz and the blues.

In 1955, novelist Jack Kerouac detoured from his cross-country American travels to Mexico City, where a group of junkie expatriates he had known from the New York City post-war scene had gone for the cheap and plentiful supply of heroin and morphine. Fellow beat writer William S. Burroughs, who had been a part of the Mexican expatriate community, had introduced Kerouac to Bill Garver (named Old Bull Gaines in the novel), a much-older, long-term addict who had in turn introduced Kerouac to Esperanza Villanueva, whom Kerouac named Tristessa in the novel.

The first book in Kerouac’s Duluoz Legend, a novella detailing the writer’s early life as refracted through the prism of the untimely loss of his brother.