1960s

By 1960, Bukowski had returned to the post office in Los Angeles where he began work as a letter filing clerk, a position he held for more than a decade. In 1962, he was traumatized by the death of Jane Cooney Baker, the object of his first serious romantic attachment. Bukowski turned his inner devastation into a series of poems and stories lamenting her passing. Jane is considered to be the greatest love of his life and was the most important in a long series of muses who inspired his writing, according to biographer Jory Sherman. In 1964 a daughter, Marina Louise Bukowski, was born to Bukowski and his live-in girlfriend Frances Smith, whom he referred to as a "white-haired hippie", "shack-job" and "old snaggle-tooth".

Jon and Louise Webb, now recognized as giants of the post-war 'small-press movement', published The Outsider literary magazine and featured some of Bukowski's poetry. Under the Loujon Press imprint, they published Bukowski's It Catches My Heart in Its Hands in 1963 and Crucifix in a Deathhand in 1965.

Beginning in 1967 Bukowski wrote the column "Notes of a Dirty Old Man" for Los Angeles' Open City, an underground newspaper. When Open City was shut down in 1969 the column was picked up by the Los Angeles Free Press along with NOLA Express in New Orleans, Louisiana, a hippie underground paper. In 1969 Bukowski and Neeli Cherkovski launched their own short-lived mimeographed literary magazine, Laugh Literary and Man the Humping Guns. They produced three issues over the next two years.