"You can't win" by Jack Black is an autobiography written in the early to mid-1920s and first published in 1926. It chronicles Black's life as a burglar and hobo across the American and Canadian West from the late 1880s to the early 1900s. Through vivid firsthand accounts, Black explores the underworld of freight-hopping, safe-cracking, and prison life, while examining crime, addiction, criminal justice, and the codes that governed the outlaw community. This influential memoir would later inspire Beat writers including William S. Burroughs.