You Can't Win is an autobiography by burglar and hobo Jack Black, written in the early to mid-1920s and first published in 1926. It describes Black's life on the road, in prison and his various criminal capers in the American and Canadian west from the late 1880s to early 20th century. The book was a major influence upon William S. Burroughs and other Beat writers.
The book tells of Black's experiences in the hobo underworld, freight-hopping around the western United States and Canada, with the majority of incidents taking place from the late 1880s to around 1910. He tells of becoming a thief, burglar, and member of the yegg (safe-cracking) subculture, exploring the topics of crime, criminal justice, vice, addictions, penology, and human folly from various viewpoints, from observer to consumer to supplier, and from victim to perpetrator.
Jack Black (1871–1932) was a hobo and professional burglar. Born in 1871 in New Westminster, British Columbia,[1] he was raised from infancy in the U.S. state of Missouri in the town of Maysville and eventually Kansas City. He wrote You Can't Win (Macmillan, 1926), a memoir or sketched autobiography describing his days on the road and life as an outlaw. Black's book was written as an anti-crime book urging criminals to go straight, but it is also his statement of belief in the futility of prisons and the criminal justice system, hence the title of the book. Jack Black was writing from experience, having spent thirty years (fifteen of which were spent in various prisons) as a traveling criminal and offers tales of being a cross-country stick-up man, home burglar, petty thief, and opium fiend. He gained fame as a prison reformer, writer and playwright. He disappeared in 1932 in a likely suicide.