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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.

©2001 Jack Black (P)2013 Audible, Inc.

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  • Jim
  • Holland, TX, United States
  • 08-10-15

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.

14 of 14 people found this review helpful

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  • Susie
  • Santa Cruz, CA, United States
  • 04-29-13

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!

8 of 8 people found this review helpful

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Wonderful tale about crime after resconstruction

If you could sum up You Can't Win in three words, what would they be?

What is success?

What was one of the most memorable moments of You Can't Win?

The author is telling the story of the first time he was arrested and stood trial. While the jury was deliberating, he made a bold escape only to later find out the jury found him not guilty.

What about Bernard Setaro Clark’s performance did you like?

His voice acting was excellent; He brought distinction to each character without over doing it, captured the slang of the period and found a rhythm that made listening a pleasure.

Did you have an extreme reaction to this book? Did it make you laugh or cry?

I laughed often, and felt it often as the author hit close to home.

Any additional comments?

A wonderful book that explores a time in history that I've never been familiar with. It captured the slang, the sub-cultures and attitudes of the time.

3 of 3 people found this review helpful

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Humdinger

This was a great look into the life of crime in the early 1900's. What a fascinating read and it is highly recommended.

2 of 2 people found this review helpful

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  • Dobbs
  • Los Angeles, Ca.
  • 11-05-16

Extraordinary

Among the best books I know. Wonderfully performed. Stunned that it took me almost fifty years to encounter it.

1 of 1 people found this review helpful

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The greatest book ever written

There has not been a more engrossing book ever written. I've read it multiple times and now the audio book has achieved the same result. It ends with my tears. Partly because of the amazing story being over (yet the rabbit hole of curiosity spirals) and partly because it ended and I have been obsessed again for hours. I love this book. The narration of the audio book is excellent. I will listen, just as I have read, many more time.

1 of 1 people found this review helpful

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  • Mark
  • Raglan, New Zealand
  • 02-20-17

Don't believe the title

Jack Black was a thief who lived in late 19th century America. There must have been plenty of them around. But what is rare, I suppose, is to find one who goes on to write a book about his escapades. This book is supposedly not fiction (although you do wonder sometimes), but rather the autobiographical details of the many robberies, burglaries and safe-crackings perpetrated by this character and his cronies. The details paint a picture so richly evocative of the era that the story has a Dickensian flavour.

Our hero (not!) travels around America and Canada and describes in great detail how he planned each of his crimes. Usually this was done with great care and professionalism, but still, many went wrong due to various unexpected mishaps that cropped up. He was apprehended many times and sometimes he got away with it, while at other times he had to serve some reasonably long sentences. He was even whipped as part of his punishment.

This was a time when in some ways it was easier and in other ways harder than today to be a criminal – Easier, because once you had escaped from the scene you were difficult to trace due to the ease of changing identities, the lack of telecommunications between police forces and the rudimentary forensic science of the times. Harder, because if you were caught in the act of a crime then it was fair game to be shot dead - with no recriminations for the shooter. This happened to a few of our hero's accomplices.

Following his adventures the listener has mixed emotions. Because he’s telling you his story you are sort of ‘on his side’ and you want him to succeed – his sense of professional pride regarding his art and chosen lifestyle seem somehow admirable. However, you have to remember that he was basically a scumbag. He had every opportunity to lead an honest life but chose not to. He never shows a shred of remorse for the misery he inflicted on his victims – well maybe he does at the end of the book, but this isn’t convincing. You also feel that there may have been a few other things that went on that don’t get mentioned, such as sexual activity. Possibly this is because the book was first published in 1926 and these topics wouldn’t have been permitted in print at that time.

Whether you like him or loathe him, whether the story is completely true or somewhat embellished, he has nevertheless left behind a fascinating record of how the criminal underworld lived before the turn of the 20th century, and this makes for excellent listening.

2 of 3 people found this review helpful

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Simply a profound masterpiece

What an amazing life story! The narrator is so good you would swear it was Blacky himself. She be required reading for all high school kids.

2 of 3 people found this review helpful

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Unlike anything you've ever heard

The author, going by the name Jack Black (Blackie), tells what he learned about crime and punishment in this memoir. His descriptions of life around the turn of the 20th century will fascinate, I'm certain.

This book is organized as chronological slices of life with analysis along the way. Blackie is thoughtful, even endearing. But he's a pure thief. His tales span everything from picking the pockets of a passed-out drunk to nighttime residential burglaries where he removes valuables from under pillows of sleeping victims.

I thought going in this entire book might be a composite of criminals. Listening convinced me though it's all genuinely represented. Later, after finishing the book, I saw the Thomas Callaghan (aka, Jack Black) photo online in the January 5, 1912 edition of the San Francisco Call newspaper.

Blackie crafted his tale as something of a lost soul wandering through a sad existence. I believe this represented his state of mind at the time of the writing but not during his youth. He acquired a philosophical attitude, perhaps a result of so much time being incarcerated.

The narration was outstanding as I sensed it was Blackie's.

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An earlier time.

I've always wondered about HOBOs Living in pipe cities and travelling the rails, avoiding the bulls. I'd say this would be an interesting way to teach history of this era. Enjoyable.