Steven Martin's Opium Fiend led me to another great book -- You Can't Win by a different Jack Black (1871-1932). I was surprised that I hadn't heard about this book or encountered it before. It's a fun read and a detailed depiction of criminal, hobo, and prison life in the late 19th and early 20th centuries.
The memoir has many interesting parts that are nearly lost history. Black became a habitual opium smoker -- in part to calm the nerves that come from house burgling -- and then a sick addict. Thus the book is an important source for Martin for his opium book. It was also championed and introduced in a later edition by William S. Burroughs.
The memoir also offers several portraits of prisons, jailers, and penal systems. Black does relatively well -- and reads widely -- in a Canadian prison, but no talking is allowed at all. For calling out to a friend, Black is put on bread and water. He also describes receiving two lashings at the start and end of one prison stint; the lashings are actually part of the Canadian judge's sentence. This is one of Black's more harrowing, character-forming experiences.
Black writes very well -- he's vivid, dramatic, thoughtful, and articulate. As an extra bonus, on occasion, he discusses criminal vernacular and the sources of various underworld terms, including bum, yegg, pegged, dan, and others.
Anyone interested in the last days of the Wild West, hobo jungles, and criminal history should read this book.