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You Can't Win, the Autobiography of Jack Back
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You Can't Win, the Autobiography of Jack Back

4.36  ·  Rating Details ·  2,280 Ratings  ·  275 Reviews
A reader's review: "The autobiography of a turn of the century hobo/safe-cracker/cat-burglar. It's down-to-earth, straightforward and amazingly graphic for its era. I found my first copy in a boxcar in a freight yard in Ohio...not for the faint of heart; a must read for us old rounders."
ebook, 279 pages
Published December 1st 2011 by Feral House (first published 1926)
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James Thane
Aug 25, 2014 James Thane rated it really liked it  ·  review of another edition
Shelves: crime-fiction
This book, newly reissued in a very nice trade paperback edition by Feral House, was first published in 1926, written by Jack Black, a drifter, hobo, small-time criminal, drug addict and jailbird who finally went straight and wound up with a job at a newspaper in San Francisco.

Black left home as a young boy and took to the road. Falling in with other drifters, he was apprenticed in a life of crime that included valuable lessons in casing a job, breaking and entering, cracking safes, fencing stol
Jun 02, 2013 Rod rated it it was amazing  ·  review of another edition
It's kind of like a Jimmie Rodgers song in book form; hopping trains, "riding the rods," hobos, gambling, hold-ups, violent deaths, prison, duplicitous backstabbers, tried-and-true pals, pistol-packin' papas (and mamas); it's just about all in there. I'm a sucker for that kind of stuff if it's done well—and this is done very well—so I loved every minute of it. Some critics have called into question the veracity of Black's "autobiography," but to me it just doesn't matter whether he told the abso ...more
Jan 04, 2012 Hank rated it liked it  ·  review of another edition
I read this book while tramping up and down the East Coast. There were four of us and then there were three of us, our most grizzled and seasoned tramp abandoning us in New York City. He bummed this book off a girl in Pittsburgh, a girl he got wet without ever touching her. She borrowed the book from a former tramp who has the words "You Can't Win" tattooed on his neck. The book was passed from gentleman to gentleman who each dreamed of hopping trains across America. Some of us did more than dre ...more
Patrick O'Neil
May 26, 2010 Patrick O'Neil rated it really liked it  ·  review of another edition
I didn't know before I starting reading You Can't Win that this was supposed to be William S. Burroughs' favorite book, or that he admired it, or... who the hell really knows what the true story is, or what's a marketing ploy. But I was kind of disappointed because the narrative voice and style was eerily similar to Junkie, Burroughs' first novel. Did Burroughs outright steal this from Jack Black? I had the same feeling while reading John Fante's work - it sounded exactly like Bukowski. Chinaski ...more
Kevin Farrell
Mar 14, 2012 Kevin Farrell rated it it was amazing  ·  review of another edition
I thought the book was great. I read it with tremendous interest. Jack Black wrote this in 1926. He wrote about a lot of things that I am curious about - riding the rails, tramping in general, being a thief, doing time in prison. Now I said I was curious but I did not mean that I have any desire to repeat his experiences. I meant that I really wanted to get a fresh view from his perspective. And it was fresh. At times it was like Hollywood shows it, at other times completely different.

He wrote a
May 15, 2014 DeAnna rated it liked it  ·  review of another edition
I am not really getting why people are reviewing this book so highly. I thought that it got a bit boring: In and out of jail and onto the next heist is most of the book.

I enjoyed the beginning and thought the book held promise. It was well written and he is a pretty interesting guy, but the charm wore off. It was only the suspense of the crimes as he committed them that really drew me in. Even when people died in the story, it didn't really engage me, emotionally.

I suppose that just for the fac
Dec 04, 2013 Danny rated it really liked it  ·  review of another edition
You Can’t Win is a romance story, or at least it’s romantic. It’s about deviating from the path that’s expected of you to one of your own choosing, a path free from the influence of government and polite society. On this second path, your responsibilities are governed only by a transactional code of honour between you and the person next to you; a compelling idea in the world of 2012.

And that would be the entirety of the book – if you only skimmed the introduction by William S. Burroughs and the
A major inspiration for Burroughs, it seems, this is a book unlike many else. How many other stories are there of 19th Century vagabonds and junkies? Equal parts Genet and Deadwood, this shows the side of America at that time left out of conventional narratives, whether that narrative is the Hollywood Western or the Victorian novel of manners. Here is a uniquely filthy, depraved world, albeit one not without camaraderie and hope, depicted with grace and passion. For those of us who have an inter ...more
Feb 20, 2008 Randy rated it really liked it  ·  review of another edition
one of my favorite parts of this book is when the author describes the wino scene in turn-of-the-century san francisco. it's basically a large common room, everyone brings their own cup, there are people laid out along the walls, passed out drunk. there is a huge pot of stew, with ingredients coming from whatever scraps were on-hand. once a day the dead are culled from the sleepers and taken out to free up space for the next hopeless drunk.
Dave Russell
Mar 13, 2007 Dave Russell rated it really liked it  ·  review of another edition
I bought this book at a now defunct left wing bookstore. I bought because I felt guilty about browsing so long. A wonderful autobiography, and perhaps the best I've ever read by a nonprofessional writer. A fascinating life this guy lead.
Mar 17, 2014 Mcgyver5 rated it really liked it  ·  review of another edition
Shelves: history
Loved it. I loved the window it gives into the late 19th century, a time before police radios, credit checks, and widespread fingerprinting. A time when paper money was not completely trusted. A time when grizzled civil war veterans populated hobo jungles and strait jackets were used to punish prisoners.

I also loved it from a security perspective. The author's objectives (anonymity, recon, break-ins, secure drops) were analogous to those of a computer hacker and he came up with some ingenious ha
Johnny Thief
May 24, 2016 Johnny Thief rated it it was amazing  ·  review of another edition
Such an insanely refreshing book. Written in another time when this was a far simpler country, this book is free of today’s silly attempts to fuse literature with mass marketing. There are no writing styles, no flashy gimmicks to wow lit agents, no dumbed down PC dialogue for the pampered YA market. Just simple, strong, fluid, beautiful writing.

Jack Black does what Kerouac strived so hard to and just couldn’t get right from his aunt's basement in Bayonne, he grabs you by the wrist and hauls you
Aug 08, 2007 Sara rated it it was amazing  ·  review of another edition
Shelves: nonfiction, favorites
Jack Black's amazing life story, filled with petty thievery, narrow escapes, prison breaks, and hobo jungles. An insider's look at transience and crime in Depression Era America. A truly unique book.
Aug 24, 2013 Caty rated it it was amazing
Anyone who has ever even broken the speed limit should read this. A bit too individualist and product of its time, but other than that...
Jan 27, 2012 Phillip rated it it was ok  ·  review of another edition
This is a fun book. It reads like an Edgar Rice Burroughs novel, which makes sense because it was first published in 1926. It presents itself as an evangelical testament to the evils of a life of lawlessness.

The narrator describes his many misadventures as a professional thief. In his eyes the highest thing a person could be was a member of the 'Johnson Family'. The Johnson Family refers to people who mind their own business and who will aid others to stay out of the hands of the law.

The novel i
Jeanette  "Astute Crabbist"
"Justice is a word that resides in the dictionary. It occasionally makes its escape, but is promptly caught and put back where it belongs." Every bit as true today as it was when this book was written. Probably even more true nowadays.

"My experience with short rations in many places has convinced me that we would all be healthier and better nourished if we ate half as much food and chewed it twice as long." Another bit of wisdom from Jack Black that has more relevance today than it did when he
Mat Barnett
Mar 08, 2016 Mat Barnett rated it really liked it  ·  review of another edition
You Can't Win is the memoir of freight-hopping hobo outlaw Jack Black. Black claimed his childhood hero was the outlaw Jesse James and it was this fascination that first inspired the young Black to ride the rails in search of frontier adventure at the close of the 19th century. We follow Blacks forty year journey - from railyard to railyard - across the United States and Canada. Along the way there are extended stops at opium dens, hobo conventions and multiple prisons of increasing infamy. Blac ...more
Scott Cox
This is an excellent book to give to budding juvenile delinquents. Though we are not certain of the true identity of the man called "Jack Black," this autobiography vividly portrays a man who lead a life of crime and who felt that "Society represented law, order, discipline, punishment. Society was a machine geared to grind me to pieces. Society was an enemy." His childhood takes place in Missouri, but he quickly goes on the road and speaks of pre-1906 earthquake era in San Francisco's tenderloi ...more
May 20, 2015 Dhaval rated it really liked it  ·  review of another edition
Have you ever thought what it would like to be a thief? To be a professional burglar? What would it feel like to getaway with a heist? I surely have daydreamed about it! This is the autobiographical story of Jack Black, professional thief/burglar, who lives a life of crime within a code of thievery. Do not steal from the little old lady landlord, but that jeweler or banker is fair game. Most enjoyable about the book is the rawness and lack of duplicity. Mr. Black has no scruples about his chosen ...more
James Newman
Oct 24, 2013 James Newman rated it really liked it  ·  review of another edition
Was made aware of the title through reading The Place of Dead Roads by WSB and was delighted to see the passages that he had lifted from memory after all those years. This is a pulp style biography of a drifter and criminal and occasional addict who lived by a code of ethics that are probably higher than your average New York or London banker.
Recommended historic yarn of a life of crime and punishment.
Peter Smith
Aug 06, 2014 Peter Smith rated it really liked it  ·  review of another edition
Salt Chunk Mary's jamboree. "Sanc [the Sanctimonious Kid] and I were fortunate enough to witness the windup of one of her most memorable celebrations. Leaving her hack at the curb, she walked into her victim's saloon and ordered all hands to drink. When the drinks were disposed of and paid for, she put both hands on the inner edge of the bar and pulled it over on the floor. Out of the wreckage she gathered in armful of bottles. One of them was accurately hurled into the mirror and the remainder ...more
Sep 12, 2016 Tatu rated it liked it  ·  review of another edition
Picked this up cause i heard it was an inspiration to the Beats, Burroughs especially lauded it. The theme intrigued me also: the tale of a thief at the turn of 19th to 20th century America, with traces of the Wild West. In fact, in the beginning Black recalls how as a boy he read the news of the killing of Jesse James, which inspired him to look for adventures in the underworld. And there indeed did he dwell for a good many years, doing numerous burglaries and smoking opium.

The book doesn't ge
Mar 31, 2014 Jannell rated it really liked it  ·  review of another edition
Written very plainly which makes it read realistically. It was an interesting story about being a criminal, but I found the stories from the prisons and jails to be the most memorable. While living outside the law sounds like a blast - those jail stories were scary. I heard they are making this into a movie. It would adapt to a script easily.
May 16, 2009 Walter rated it liked it  ·  review of another edition
A fun book, I always wanted to know what a “highwayman” was.
That said: most of it is bullshit. But fun bullshit.
There is dialogue where some "highwayman" mentions “Psychology”.
Considering when this book was written I find that hard to believe.
Some of this book was written by someone other than “Jack Black”.
Feb 13, 2009 Corey rated it it was amazing  ·  review of another edition
Perhaps my all-time favorite. What is there to say about a man beaten down by life, looking back at the mistakes he's made? The humor and violence of Jack's life are really remarkable. The stories he has to tell about "The Johnson Family" of hobos and thieves are just incredible.
Dec 24, 2008 Matthew rated it it was amazing  ·  review of another edition
Recommends it for: people who like themselves.
Recommended to Matthew by: matteo vianello
hobos, bulglarly, murder, prostitutes, prison, heroin.

true story. amazing. An America I actually wish still existed.

skip the last chapter (unless you want to read a 1920's version of the last five minutes of a full house episode), but read the epilogue about the author's death.
C. James
Mar 02, 2014 C. James rated it really liked it  ·  review of another edition
I remember my father discussing this one which he read when it came out in 1926. My curiosity got me a copy of the Nabat/AK Press edition published in 2000. All but forgotten, this autobiography of a career criminal covers Jack Black's life from his drifting away from his widowed father, leaving the convent school at 14. His heroes were bitter, Civil War veterans, Jesse James and the bartender for whom he worked. His drift into crime came with natural ease as he acquired skill as a thief, safe c ...more
This book was fantastic. Socially relevant to now. It's to do with an old timey train hopping hobo and his life of crime and rehabilitation. Straightforward and fascinating. Filled with adventure, compassion and musings on the human condition. I loved it.
Jason Minor
Oct 27, 2014 Jason Minor rated it it was amazing  ·  review of another edition
Fascinating book. A glimpse of the criminal underworld between the fall of the James boys and the rise of Al Capone, as told by one who lived it. The autobiography of Jack (Blacky) Black, a small time thug and failed thief. The writing is amazingly elegant, fluid, and contemporary (which makes it a little jarring when he makes references to hanging out with the old vets - Civil War vets). Other than the references that bring you back to the time frame, the book could have been written today. It' ...more
Turok Tucker
Aug 25, 2015 Turok Tucker rated it it was amazing  ·  review of another edition
Honest, entertaining, and eye-opening. Black, working under the monoger of "Blacky", became a luckless, dedicated, tough highwayman and robber. His most entertaining stories in this autobiography deal with his many attempts at a big score -- with never a predictable result. The reader is able to witness and feel the zeitgeist of the American underground at the time, our capitalist - dog eat dog - criminal system. Blacky comments on the inaccuracy of justice. One of his bigger scores leads to a t ...more
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John Black was a late 19th century/early 20th century hobo and professional burglar, living out the dying age of the Wild West. He wrote You Can't Win (Macmillan, 1926) a memoir or sketched autobiography describing his days on the road and life as an outlaw. Black's book was written as an anti-crime book urging criminals to go straight but is also his statement of belief in the futility of prisons ...more
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“I was wrong. I knew I was wrong, and yet I persisted. If that is possible of any explanation it is this: From the day I left my father my lines had been cast, or I cast them myself, among crooked people. I had not spent one hour in the company of an honest person. I had lived in an atmosphere of larceny, theft, crime. I thought in terms of theft. Houses were built to be burglarized, citizens were to be robbed, police to be avoided and hated, stool pigeons to be chastised, and thieves to be cultivated and protected. That was my code; the code of my companions. That was the atmosphere I breathed. 'If you live with wolves, you will learn to howl.” 5 likes
“Instead of finding fault with the fire, I gave thanks for the metal to take the temper and hold it.” 3 likes
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