Jack Black

Jack Black was a late 19th century/early 20th century hobo and professional burglar, living out the dying age of the Wild West. He wrote You Can't Win (Macmillan, 1926) a memoir describing his days on the road and life as an outlaw. Black's book was written as an anti-crime book urging criminals to go straight but it is also his statement of belief in the futility of prisons and the criminal justice system, hence the title of the book.

Jack Black is an essentially anonymous figure (even his actual name is uncertain) who is recognized through association with William S. Burroughs. Although his philosophy on life was especially influential to Burroughs, who associated with similar characters in his early adulthood and mirrored the style of You Can't Win with his first published book, Junkie, Black's writings also had a profound effect on the writings and lives of all the Beat Generation.

After his last spell in prison Jack Black became friends with wealthy patron Fremont Older and worked for Older's newspaper The San Francisco Call. He worked on his autobiography with Rose Wilder Lane and eventually composed essays and lectured throughout the country on prison reform. He was also rumored to have received a stipend of $150 dollars a week to draft a screenplay titled Salt Chunk Mary with co-author Bessie Beatty, based around the infamous vagabond ally and fence of the same name in You Can't Win. The play flopped, although he was able to attain some amount of popularity, which subsided quickly.

He is believed to have committed suicide in 1932 by drowning, as he reportedly told his friends that if life got too grim, he would row out into New York Harbor and, with weights tied to his feet, drop overboard. In You Can't Win Black describes this state of mind as being "ready for the river."