Early writing

When Bukowski was 24, his short story "Aftermath of a Lengthy Rejection Slip" was published in Story magazine. Two years later, another short story, "20 Tanks from Kasseldown", was published by the Black Sun Press in Issue III of Portfolio: An Intercontinental Quarterly, a limited-run, loose-leaf broadside collection printed in 1946 and edited by Caresse Crosby. Failing to break into the literary world, Bukowski grew disillusioned with the publication process and quit writing for almost a decade, a time that he referred to as a "ten-year drunk". These "lost years" formed the basis for his later semi-autobiographical chronicles, although they are fictionalized versions of Bukowski's life through his highly stylized alter-ego, Henry Chinaski.

During part of this period he continued living in Los Angeles, working at a pickle factory for a short time but also spending some time roaming about the United States, working sporadically and staying in cheap rooming houses. In the early 1950s Bukowski took a job as a fill-in letter carrier with the U.S. Postal Service in Los Angeles but resigned just before he reached three years' service.

In 1955 he was treated for a near-fatal bleeding ulcer. After leaving the hospital he began to write poetry. In 1957 he agreed to marry small-town Texas poet Barbara Frye, sight unseen, but they divorced in 1959. According to Howard Sounes's Charles Bukowski: Locked in the Arms of a Crazy Life she later died under mysterious circumstances in India. Following his divorce Bukowski resumed drinking and continued writing poetry.