You Can't Win is the pioneering American criminal underworld memoir written by Jack Black, a burglar, drifter and criminal active in early 1900's America. Black's astonishing accounts of hopping trains, cracking safes, escaping prison cells, and drug addiction offers 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, deadpan and humorous memoir, the author recaptures the transient underworld of the early twentieth century. In You Can't Win, the reader will meet unforgettable underworld characters as diverse and fascinating as: 'Foot and a Half George'; 'Salt Chunk Mary'; 'The Sanctimonious Kid'; 'Soldier Johnnie'; and others.

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 North America in the early 1900's. The book 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, and doing time in jails and prisons. The vices and addictions Black reveals include alcoholism, abuse of opium ('hop'), gambling, prostitution, and stealing.

*NOTE: Potentially offensive ethnic slang appearing in the original text has been modified