Jack Black was a hobo and professional burglar. Born in 1871 in New Westminster, British Columbia, he was raised from infancy in the U.S. state of Missouri. He wrote You Can't Win, a memoir or sketched autobiography 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 was writing from experience, having spent thirty years as a traveling criminal and offers tales of being a cross-country stick-up man, home burglar, petty thief, and opium fiend. He gained fame through association with William S. Burroughs, and his writings had a profound effect on the writings and lives of all the Beat Generation.
Life
Jack Black is an essentially anonymous figure; even his actual name is uncertain. Some 1904 news articles name him as Jack Black, alias Tom Callahan, while a 1912 newspaper article names him Thomas Callaghan, alias Jack Black, and another gives his alias as Harry Klein. One of his nicknames among criminals was Blacky. After his last spell in prison, 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 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. His philosophy on life was especially influential to William S. Burroughs, Burroughs associated with similar characters in his early adulthood and mirrored the style of You Can't Win with his first published book, Junkie.
Disappearance
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".
