You Can't Win

  • by Jack Black
  • Narrated by Bernard Setaro Clark
  • 10 hrs and 41 mins
  • Unabridged Audiobook

Publisher's Summary

The favorite book of William Burroughs. A journey into the hobo underworld, freight hopping around the still Wild West, becoming a highwayman and member of the yegg (criminal) brotherhood, getting hooked on opium, doing stints in jail or escaping, often with the assistance of crooked cops or judges. Our lost history revived.
With an introduction by Burroughs. A BookSense 77 selection.

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Hobo Jack

When I find an obscure book and write about it I discover ten thousand others have already read the thing. It's like being an explorer in a remote jungle who finds Starbuck cups in the undergrowth from those who already passed that way. But, most book readers are not aware of You Can't Win, as I was not until a few weeks ago. It's the non-fiction autobiography of a self-chosen outcast in the late nineteen century, who despite a good upbringing chose at sixteen to hop trains and live life as a petty burglary and sneak thief. "The life fascinated me," he says. Once settled into it he refused to do anything else. Older men and boys taught him safe cracking and how to sneak into houses at night. They educated him on how to fence jewelry, hide swag, tear up receipts, and dress blandly to be just a face in the crowd. It's enthralling. You Can't Win was penned forty years after Jack Black became a criminal, and after a long jail term finally changed his attitudes. In late middle age he was paroled and handed a decent job by a wealthy newspaper publisher, who also arranged for his memoirs to be ghost-written—this, as the author's health (despite statements to the contrary) slid downhill slowly. His book was a hit when it came out in 1926 but Black, or Blackie as his friends called him (his real name may have been Thomas Callaghan), grew enfeebled. He wasn't able to do the sequel his publisher pestered him for. Depressed about his health, he drowned himself in the Pacific in 1932.
Read the book with contemporary knowledge of crime and psychology and it's a gem of unintended revelation. For example, readers familiar with criminal ways will recognize the use of nicknames to disguise identities. Legendary bank robber Alvin Karpis, for example, always called himself "Ray." Baby Face Nelson's name among his fellow criminals was "Jimmy." At present, cops keep databases of "street names" in order to fit nicknames to faces. Nicknames were already used in the late 1880s when Blackie began his career. Another thing to note is the author's touch of narcissistic personality disorder. The first time he saw someone killed—a boy near his age crushed to death by shifting lumber in a boxcar the two were riding, so that just legs could be seen dangling down in free space—he was unmoved. He kicked panels out of the boxcar's side and legged it away. The second time his best friend, mentor, and fellow burglar "Smiler" was shot in the throat in a dark backyard while breaking into a house. Blackie ran away again. He forced himself to return, he writes, and drag his friend into an alley—where he rifled Smiler's pockets, taking his money and watch. To be fair, "Smiler" was dead and might well have done the same for him were circumstances reversed. The author witnesses two other deaths before the book concludes. None caused an emotional ripple. There is no emotional connection between himself and those around him, only reciprocal loyalty. What Blackie valued was fair dealing and professional conduct by peers—elements defining a "first class thief." The only females mentioned in depth are nuns and prostitutes. Interesting. Blackie spent much time mentored by older men as he learned his trade in hobo jungles and jails. In these places teenage boys were highly prized by "jockers" who used them as "punks." The minor genre of hobo memoirs are quite frank about these goings-on. There is not a peep about this from the author. At the end of the book Mr. Black blames bad treatment in jails for high crime rates and recidivism, which rings rather hollow. Blackie's propensity for crime was part of his teenage personality, possibly a predisposition in a boy who was privately educated with advantages others never possessed. In the end, he places more blame on environment than his own psychological mix.
There is a movie coming out based upon this book which I suppose will stink, although one always hopes for the best. Meantime . . . I highly recommend this book for those interested in this sort of peculiar subject. It is engaging and interesting and the narrator, Bernard Clark, does a good job.
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- Jim

The Original Hobo Narrative

This is the real deal: the original Depression-era train-hopper hobo narrative. It’s so poignant and beautifully written, it never went out of print.

Jack Black's clean, uncluttered prose— and complete lack of self pity— make it easy to feel present in the book to this day.

When William S. Burroughs came along, years after this book was published, he wrote it was “the best book I ever read.” His intro to this edition "You Can’t Win" helped it become the cult classic of a new generation. You can really see Black’s influence on the Beats.

"You Can't Win" in one of the best memoirs I’ve read: freight-hopping, a brotherhood of theives, drugs, prison—and, profoundly, librarians.

—Rip-roaring introduction by Burroughs, included!
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- Susie

Book Details

  • Release Date: 04-16-2013
  • Publisher: Audible Studios