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.

Summary

The book tells of Black's experiences in the hobo underworld, freight-hopping around the western United States and Canada, with the majority of events 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.

Publication

You Can't Win originally appeared in serial format in the San Francisco Call-Bulletin under the editorship of Fremont Older. It was so popular that it was reissued in book format by MacMillan and became a best-seller. The 1988/2000 Amok Press edition contains a foreword by Burroughs, this edition received numerous reviews.

Adaptations

The book has been adapted to a film titled You Can't Win directed by Robinson Devor starring Julia Garner, Jeremy Allen White, Will Patton, Charles Baker, Nina Arianda, Rusty Schwimmer, James Hong, and Michael Pitt who co-produced and co-wrote the screenplay. Also, co-wrote by Barry Gifford. The film was released in 2026. Shot on location in Port Townsend, Washington and Guthrie, Oklahoma. Produced by Robert Scarff.

References

  • Full text of You Can't Win at HathiTrust Digital Library