"You Can't Win" is an autobiography by adventurer Jack Black, written in the early to mid 1920s and first published in 1926. The book tells of his experiences in the hobo underworld, freight-hopping around the still Wild West of the United States and Canada. He tells of becoming a thief, burglar, and member of the yegg 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.The main criminal activity of Black's life and of the book is thievery, which leads to discussions of various technical aspects of the thief's "trade", including casing of prospects, safe-cracking, fencing of stolen goods, the disposal of evidence, the maintenance of aliases and avoidance of attention or traceability, the social networks of criminals, the experiences of being arrested, questioned, and tried, and the experience of doing time in jails and prisons. The vices and addictions Black discusses include alcoholism, abuse of opium, gambling, prostitution, and stealing.William S. Burroughs cited "You Can't Win" as an extremely influential book in his life, and lifts the book's style and stories in his 1953 book "Junkie." Black's writings also had a profound effect on the writings and lives of all the Beat Generation.

Einstein Books' edition of "You Can't Win" contains supplementary texts:* "Letter From A Master Addict", by Beat Generation author William Burroughs.* "Howl", by Beat Generation poet Allen Ginsberg.* "Big Rock Candy Mountain", the original lyrics of hobo busker Harry McClintock.