You Can’t Win, by Jack Black, 1926, reprinted by Nabat Press, 2000.
This is an interesting, conflicted, tripartite book. It’s an autobiography of a hobo and burglar, a jailbird, and a reform activist. The book starts as a good-natured telling of how Black left home, and became a hobo. We follow him as he gets caught up in the seamier side of life away from home, and how, ostensibly, through misunderstandings, he came to fall fully on the wrong side of the law. The arc continues through opium addiction, prison, abuse, and ends in reform and moral outrage.
The first part of the telling is a light, almost romantic adventure. The young man goes off, has adventures in the city, then starts to ride the rails. Sure, there’s danger, there’s police and railyard bulls to avoid, there’s even sudden death from shifting cargo, but the telling is almost with the exuberance of youth. Black encounters other hobos, who welcome him into the family, teach him the argot, and start showing him the ropes.
From here, the tale darkens. Black apprentices himself out to be a burglar, and the situations get more perilous. Friends get killed; Black gets into and out of prison. Still, the tale is rip-roaring adventure: now a member of the brotherhood of thieves, Black introduces us to a cast of wild characters. He describes to us the great hobo gatherings, with their camaraderie and drunken abandon. He details many hair-raising exploits of burglary and safe breaking.
The latter part of the book involves a lot more prison, betrayal, and drug addiction. It still has elaborate capers of theft and jailbreak, but now Black has suffered under the system. Authority is now beating him down, and he responds with wantonness and violence. In the end, there is kindness and reform.
The book is particularly intriguing in the shift of tone throughout the book. There is definite pride in the exploits, even if the words condemn his actions. The latter parts of the book are quite bitter, and the emotions are contradictory — Black blames the cruel neglect and abuse of society for making him into a monster, yet he also happily admits that he never had any interest in becoming part of society or behaving in a way that society would accept. This is what makes the book more than just a personal journey or a thriller; we experience the world from Black’s perspective, seeing hypocrisies in both the society with which he’s in conflict, and in his antisocial lifestyle.