You Can’t Win

A very pleasant re-read of this classic, a perpetual staff pick at Green Apple Books. Published in 1926, Jack Black’s autobiography describes life on the road with the bums, Johnsons, yeggs, fellow travelers. Black gets his start working for a barman, sweeping up the bar, in order to purchase a dapper grey suit he sees on another man. From this job, he collects money for the milkman from the local whorehouse and is busted by police when one of the customers claims to be robbed; Black’s first taste of jail. He helps one of the girls escape from the bordello, and eventually leaves town to try life on the road. His first night, he is accepted into the camp of two bums who give him a quick primer on bumdom. He rides the rails, falls in with the upper crust of bums, learns burglary and safe cracking. Ultimately this life of crime turns into a tale of jails in the US and Canada. He acquires an opium habit which he sheds after escaping jail, convinced that addition is purely mental. He is ultimately rescued from the prison cycle by Fremont Older, who gives him a job as librarian for the San Francisco Call.
Fantastic glimpse at turn of the century San Francisco, Denver, Kansas City, Vancouver.
Addendum: a few days after posting this, I was eating at Souley Vegan in Oakland and spotted a chap there wearing an AK Press sweatshirt, the publishers of this rescued work!