You Can't Win is the pioneering American criminal underworld memoir written by Jack Black, a burglar, drifter, and criminal active in early 1900s America. Black's astonishing accounts of hopping trains, cracking safes, escaping prison cells, and drug addiction offer an unusually vivid portrait of American underworld life over a century ago.

Beat legend William S. Burroughs ("Junkie") cited the book as influential in his life and writing. In his striking, and often deadpan and humorous, memoir, the author recaptures the transient underworld of the early 20th century.

In You Can't Win, the listener will meet unforgettable underworld characters as diverse and fascinating as Foot and a Half George, Salt Chunk Mary, The Sanctimonious Kid, Soldier Johnnie, and many more.

With an accompanying bonus glossary of hobo, tramp, and transient terminology, You Can't Win tells of Black's experiences in the hobo and criminal underworld, freight-hopping around the United States and Canada from the late 1880s to the early 1900s.

The audiobook is among the first to introduce the fascinating "yegg" subculture, a prototypical form of criminal hobo or bum prevalent in the USA around the turn of the century. You Can't Win is a must-listen for fans of true crime, American history, Beat writers, and hobo-yegg culture.

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: the casing of prospects (surveillance of targets), safe-cracking, fencing of stolen goods, the disposal of evidence, maintaining aliases and avoiding attention or traceability, the social networks of criminals, the experiences of being arrested, and the experience of doing time in jails and prisons. The vices and addictions Black reveals include alcoholism, abuse of opium ("hop"), gambling, prostitution, and stealing.

PLEASE NOTE: When you purchase this title, the accompanying PDF will be available in your Audible Library along with the audio.