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4.35  ·  Rating details ·  2,561 Ratings  ·  301 Reviews
An amazing autobiography of a criminal from a forgotten time in American history. Jack Black was a burglar, safe-cracker, highwayman and petty thief.
Kindle Edition, 279 pages
Published (first published 1926)
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Community Reviews

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James Thane
Aug 25, 2014 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
Jan 24, 2011 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 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
Nov 08, 2007 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
Patrick O'Neil
May 20, 2010 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 12, 2012 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
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
Jul 16, 2012 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
Nov 27, 2007 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 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.
Nov 25, 2013 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
Aug 08, 2007 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 17, 2013 rated it it was amazing  ·  review of another edition
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...
Bugün artık ne ifade ettiği bilinmeyen çok satar yeraltı edebiyatı soslu eserlerin yanında parıldayan güçlü bir kaybeden otobiyografisi, belki de kaybetmiyordur hem kim kazanıyorki hayat denen herzeyi.
Jan 27, 2012 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
Johnny Thief
May 19, 2016 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
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
James Newman
Oct 24, 2013 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.
John Porcellino
Oct 21, 2012 rated it it was amazing  ·  review of another edition
Shelves: history, literary
Having heard of this book through my studies of the Beat Generation writers (they were deeply inspired by it, especially Burroughs), imagine my surprise when I found a first edition copy in an antique shop in Morrison,CO for only $2.00! (It's been reprinted and is easily available now.) The sordid, autobiographical tale of a petty criminal and wanderer, You Can't Win is a fascinating book, and necessary reading for Beat Generation fans.
Oct 08, 2013 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 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”.
Jan 08, 2008 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.
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.
Feb 13, 2009 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 28, 2015 rated it really liked it  ·  review of another edition
Definite classic that not many seem to have read.
Aug 02, 2017 rated it it was amazing  ·  review of another edition
I'd say this book is prophetic, but the truth is really just that not much has changed in 100+ years. Bigger picture, I mean. Of course, as a biography, it's a glimpse into an era that doesn't much exist anymore. A "way of life that is gone forever," as Burroughs writes in the introduction. Which is what makes the contrast with the aspects that haven't changed a bit even more fascinating.

Below are several excerpted quotes from the end of the book, including the appendix, which is from a Harper's
Peter Smith
Mar 16, 2017 rated it it was amazing  ·  review of another edition
This book has been a long time coming for me. I first heard of it back in college some 20+ years ago casually mentioned by William S. Burroughs (who apparently was heavily influenced by it) so I added it to my pre-Goodreads "to-read" list. The problem then was that it had been out of print for many years and I couldn't find it anywhere. Fast forward 20 some years and this reprinting comes out so I finally got my hands on it. And luckily, unlike some books I've waited for only to be let down by t ...more
Rivière Cécile
Ah les éditions Monsieur Toussaint Louverture ! Jamais déçue et ce deuxième livre de la collection des Grands animaux me le confirme ! Une écriture simple et honnête malgré le genre de l'autobiographie et de ce fait une plongée dans l'Ouest américain des hobos de la fin du XIX début XX. Une nouvelle réussite !
Ma chronique plus longue par ici : https://akathegirlwhoreads.wordpress....
Feb 16, 2017 rated it really liked it  ·  review of another edition
This is a book like none other: an honest, plainspoken autobiography by a small time criminal in the old west/Barbary coast a century ago. Not sensationalized, not exaggerated, not looking for grand themes or heroics, which makes it the rare self assessment of an unimportant life full of bad decisions (which makes it far more interesting than most biographies)
Dan Young
Sep 13, 2017 rated it really liked it  ·  review of another edition
Filled with whimsy, a good primer on why prisons are stupid and why crime is rad.
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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.” 6 likes
“There were times when I thought I got a bit more punishment than was coming to me, but I don't regret a minute of it now. Each of us must be tempered in some fire. Nobody had more to do with choosing the fire that tempered me than myself, and instead of finding fault with the fire I give thanks that I had the metal to take the temper and hold it.” 5 likes
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