Jack Black

Born in 1871, Jack Black was a Canadian-born American drifter, burglar, and writer best known for You Can't Win, first published in 1926. The book draws on his years riding freight trains, living as a hobo, serving time in prison, and moving through the underworld of the American and Canadian West.

What makes his work last is its mix of adventure and honesty. Rather than glamorizing crime, You Can't Win argues that prison and poverty could trap people in a cycle that was hard to escape, even when they wanted to change.

Black died in 1932. His memoir later reached a wide literary audience and became especially well known for its influence on later writers, including William S. Burroughs.