You Can't Win
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You Can't Win

4.39 of 5 stars 4.39  ·  rating details  ·  1,621 ratings  ·  228 reviews
You hold in your hands a true lost classic, one of the most legendary cult books every published in America. Jack Black's autobiography was a bestseller and went through five printings in the late 1920's. It has led a mostly subterranean existence since then - best known as William S. Burrough's favorite book, one he admitted lifting big chunks of from memory for his first...more
Paperback, 279 pages
Published April 1st 2001 by Nabat Books (first published 1926)
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Cult Classics
111th out of 354 books — 600 voters
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My Cult Fiction
14th out of 30 books — 6 voters

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James Thane
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...more
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
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
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...more
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...more
Kevin Farrell
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...more
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...more
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
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.
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.
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...
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...more
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...more
James Newman
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
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
Amber Snow
I sort of wish that Goodreads had a star beyond five sometimes. If they did, I would put this one there. I read this book a little over ten years ago now and I couldn't forget it. I think about this fella and his incredible balance of bad-assery and compassion all the time. This book is a cult classic and if you don't read it, you'll be super sad. His writing style is simple. So simple that the most complex of emotional, heartbreaking situations are reduced to a concentrate that socks you in the...more
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.
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”.
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 5 of 5 stars
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
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
Five stars for so many things. Read this!

I couldn't put this book down. While I know the U.S. was once a collection of territories and towns based on no more than a mine or a railroad stop, it's still hard to believe it sometimes. Jack Black shares, in terrific detail, his memories of being a hobo and thief in the late 1880s and 1890s across the U.S., before fingerprinting and photos, when friends could still saw the bars off of your jail cell and spring you (and did). Black was in Chicago for t...more
Patrick O'Neil
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
Brittany Kubes
It seems appropriate that I was reading a book titled “you can’t win” at the time I got into a self-induced bike accident. This was a nice autobio on the life of a vagabond thief ‘back in the DAY’ when cops were dirty, everyday citizens carried guns in their pockets, and the economy produced lots of poor people that turned to thievery …err, no this is not a book about 2012, but the early 1900s. Aside from the similarities to today, the value system of Jack Black and his fellow thieves was really...more
Trevor Jones
The memoir of the ethical criminal....

My brother recommended this to me out of the blue as a new entry in the "Hobo Lit" canon, and indeed it is the very filet of the genre! While I understand some readers' comments about its monotony (or duotony) at times, I think that can be the point when reading a lifelong thief and general scallywag's autobiography: Out of Jail/In Jail/Out of Jail/In Jail ad nauseuem. Black, while sounding jaded and resigned existentially to his lot in this world, manages a...more
Tara Thai
I finished reading this book a few days ago but I only now managed to write something about it.
You can’t win is the autobiography of Jack Black, a hobo, criminal, burglar pickpocket of the late 1800s and early 1900s. 35 years of history of the American street life.
Although at times the stories got a little repetitive, I truly enjoyed this read. As in the case of Le Vida Loca, the last book I read about gang life in Los Angeles, many people seemed to criticize the language in which this book is w...more
William S. Burroughs introduces this & anyone familiar w/ his work can certainly see why! Burroughs reused the characters in this bk freely. Salt Chunk Mary & the Johnsons esp. Burroughs begins his foreword w/:

"I first read You Can't Win in 1926, in an edition bound in red cardboard. Stultified and confined by middle-class St. Louis mores, I was fascinated by this glimpse of an underworld of seedy rooming houses, pool parlors, cat houses and opium dens, of bull pens and cat burglars and...more
Dec 13, 2013 Joshua rated it 4 of 5 stars
Recommends it for: lots of people
This book is one of the all-time top sellers at STORIES book store in Echo Park and I wanted to find out why. The answer is simple, the owners like the book and they continually have it end-capped in their store to sell it....but furthermore, it's a good read and suits the neighborhood. I'm glad I read it and did so quickly.

It's basically an autobiography of a life long (seemingly) non-violent criminal. The other Jack Black is a hobo thief who has the intelligence to eloquently retell his story...more
I've been occasionally spending time with Black (no, not that guy) for a longass time... for some reason I've been picking this up and putting it down for years, probably in part because its long but also because by its nature it can be read this way (there are few 'main characters' and the content is somewhat repetitive). I guess it must've been the introduction by W.S. Burroughs that brought it to my attention (which is brief and extremely spoiler-ridden, do not read before the text itself) bu...more
I picked this up because I wanted to support an Infoshop I was visiting in Austin, TX. I didn't want to buy a book and am really skeptical about a lot of books related to politics, but I remembered how the Infoshop in Atlanta struggled because people only bought t-shirts and key chains, if they bought any thing at all. I really wanted to buy something that honored the mission of providing access to alternative and progressive literature.

Somehow, You Can't Win caught my eye. Maybe I was attracte...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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“Instead of finding fault with the fire, I gave thanks for the metal to take the temper and hold it.” 2 likes
“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.” 1 likes
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