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37 of 39 people found the following review helpful:
5.0 out of 5 stars One of the most captivating books ever written
I first discovered Jack Black's `You Can't Win', as I suspect many readers did, when I found out that it was William S Burroughs' favourite book. Until I read it, though, I couldn't imagine just how big an influence it was on Burroughs - who drew upon its style, and the code of honour it describes, for the entirety of his writing career.

When you read Burroughs'...

Published on March 13, 2003 by Sandy Starr

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2.0 out of 5 stars Great book, but poor edition
I would actually warn against this edition of 'You Can't Win.' While nothing against the content of the narrative itself, this edition fails to present itself as a book of relevance; it has a terribly designed jacket with no synopsis of the memoir, there is no foreword or introduction (both of which appear in the original edition), no information about the author, and it...
Published 12 months ago by vanrambler


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37 of 39 people found the following review helpful:
5.0 out of 5 stars One of the most captivating books ever written, March 13, 2003
By 
Sandy Starr (United Kingdom) - See all my reviews
This review is from: You Can't Win (Paperback)
I first discovered Jack Black's `You Can't Win', as I suspect many readers did, when I found out that it was William S Burroughs' favourite book. Until I read it, though, I couldn't imagine just how big an influence it was on Burroughs - who drew upon its style, and the code of honour it describes, for the entirety of his writing career.

When you read Burroughs' foreword to this edition of `You Can't Win', it hits you that he didn't (as you might assume with a favourite book) reread the book regularly. Rather, he memorised the book as a boy, and then throughout his life `read' the version memorised in his own mind. Even the passages that Burroughs quotes in the foreword aren't word-for-word precise (I compared them with the text of the book proper), because they've been committed to myth and memory, and are recited in ritualistic fashion.

All of which aside, `You Can't Win' deserves to be known as more than just `the book that inspired Burroughs'. It's written in a plain, unsentimental style which has as much in common with the writing of Charles Bukowski as it does with the Beats - a style of writing which reached its apotheosis with `The Grass Arena', the harrowing autobiography of the British alcoholic vagrant John Healy. (Now, someone should teach a literature class comparing `You Can't Win' and `The Grass Arena' - THAT would be an inspiration.) What these writers have in common is that when you read them, you instantly think: `Now this is good, compelling, uncluttered prose.'

Many of those who have posted reviews below rightly praise Jack Black's memorable language and characterisation, which make `You Can't Win' into a kind of turn-of-the-century lexicon and encyclopaedia of the life of American thieves and hobos. But I was even more struck by Black's remarkable resolve, self-dependency and moral fortitude, and above all his categorical refusal to feel sorry for himself, or to let the reader feel sorry for him.

Three passages in the book in particular, all of which concern prison, are horrific - two passages in which Black is punished by flogging, and an absolutely unbearable passage in which he is tortured in a straitjacket by a sadistic prison warden. If these passages had been written by a lesser writer, I could not bear to read them. But Black takes the reader firmly by the hand, conveys what happened to him, and moves on.

Describing the first flogging: `It would not be fair to the reader for me to attempt a detailed description of this flogging.... If I could go away to some lonely, desolate spot and concentrate deeply enough I might manage to put myself in the flogging master's place and make a better job of reporting the matter. But that would entail a mental strain I hesitate to accept, and I doubt if the result would justify the effort.'

Describing the second flogging: `To make an unpleasant story short, I will say he beat me like a balky horse, and I took it like one - with my ears laid back and my teeth bared. All the philosophy and logic and clear reasoning I had got out of books and meditation in my two years were beaten out of me in 30 seconds, and I went out of that room foolishly hating everything a foot high.'

Describing being tortured in a straitjacket: `Every hour Cochrane came in and asked if I was ready to give up the hop. When I denied having it, he tightened me up some more and went away. The torture became maddening. Some time during the second day I rolled over to the wall and beat my forehead against it trying to knock myself out. Cochrane came in, saw what I was doing, and dragged me back to the middle of the cell. I hadn't strength enough left to roll back to the wall, so I stayed there and suffered.'

Black opens the book with a description of his own face, and fittingly enough, there is a photograph of him near the front of the book. Many times while reading `You Can't Win', I found myself flicking back to look at that careworn, yet amiable face, and picturing Black's exploits in my mind. The afterword to this edition, which outlines Black's life after the book was published, is equally fascinating - I was moved almost to tears to read that he simply vanished in 1932, and was strongly suspected of having tied weights to his feet and thrown himself into New York Harbour.

Of course, `You Can't Win' is a unique and priceless document of a bygone American era. But lest you find yourself feeling nostalgic for this way of life - as readers are prone to feel, whenever they read vivid descriptions of times before they were born, and as William S Burroughs is certainly guilty of feeling in his foreword - Black cautions us against precisely this kind of nostalgia (and ironically, uses an irresistibly romantic description of the past to do so):

`I'm not finding fault with these brave days of jungle music, synthetic liquor, and dimple-kneed maids, and anybody that thinks the world is going to the bowwows because of them ought to think back to San Francisco or any big city of 20 years ago - when train conductors steered suckers against the bunko men; when coppers located "work" for burglars and stalled them while they worked; when pickpockets paid the police so much a day for "exclusive privileges" and had to put a substitute "mob" in their district if they wanted to go out of town to a country fair for a week. Those were the days when there were saloons by the thousand; when the saloonkeeper ordered the police to pinch the Salvation Army for disturbing the peace by singing hymns in the street; when there were race tracks, gambling unrestricted, crooked prize fights; when there were cribs by the mile and hop joints by the score. These things may exist now, but if they do, I don't know where. I knew where they were then, and with plenty of money and leisure I did them all.'

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40 of 46 people found the following review helpful:
4.0 out of 5 stars Underworld figure talks up prison reform, September 5, 2002
By 
This review is from: You Can't Win (Paperback)
"You Can't Win," is an entertaining romp through the underworld of the American West at the beginning of the twentieth century, although the book masquerades as an anti-crime and prison reform tract. Sparsely written, yet thoroughly picturesque and descriptive, "You Can't Win" was written by Jack Black, burglar, safecracker, stick-up man, and penitentiary kingpin gone good. Traveling through a world of saloons, mining camps, and raucous western cities like San Francisco and Seattle, Black brings to vivid life a world of the 1900s we rarely see in textbooks.

In the end, Black urges us to stick to the straight and narrow, rues the path that brought him to morphine and state penitentiaries. Indeed, throughout the narrative, Black sprinkles cautionary paragraphs intended to discourage would-be imitators. But there's such a streak of enthusiasm and nostalgia running through Black's book that it's hard to believe that he regrets most of what he did. The stuff that he REALLY regrets seems to be what's left out - and there's a lot left out. That period he "terrorized" San Francisco - according to the afterword - his shooting of an unarmed man, the drug business he subsequently set up in prison.

Black's world is extremely moral, if not above the law. There's a strong sense of loyalty running through the book, and an ethical hierarchy, at the bottom of which lie "stool pigeons" and "double crossers," and at the top are the reliable men who keep their word and pay their debts. Those who make the cut, who play by the unwritten rules of lawbreaking and loyalty are the "Johnsons," the family of thieves.

No wonder those literary poseurs, the Beats, glommed onto this book as an instructional how-to, not as a cautionary tale of morality. The Beats were attracted to the underworldly anti-establishment characters, the bums, the hobos, and the fences. In the introduction to "You Can't Win," William S. Burroughs takes Black's message further by adding a second category in opposition to the "Johnsons," the "poops." (Using a different word, of course, which won't pass Amazon's censorship.) Either you're a "Johnson" or you're a "poop," Burroughs says, and with a swooping unJohsonlike gesture indicts everybody who prefers work to thievery.

Black himself would reject the notion of casting most of us into "poopdom." He had great respect for honest people, even those that he robbed. Sure they might be a bit slow, but they often plied a trade, bothered no one, and lived fulfilled. He blamed his own inability to keep straight on some mysterious internal defect, refusing to praise or justify his violent past.. Burroughs, of course, born into a life of priviledge and wealth, and who chose to squander his advantages on drugs and self-entertainment, prefers to justify his own excesses (including the shooting death of his wife) and grab onto the title of "Johnson," as if it were a badge of honor.

But putting my attacks on the Beats aside, the importance of this book lies in its examination of criminality. What makes a criminal? How can we keep young people from growing up into a life of crime? Although Black provides us with few answers, he gives us the example of his own life. He claims that his experiences in prison made him more of a criminal, and that the aggressive response of law enforcement officials to his deeds pushed him further into crime. It was the prison strait-jacket treatment that turned him bad, that put him behind a gun, that made him dangerous. And it was a judge's act of kindness that convinced him to reform. In order to cut down on vicous criminals, Black suggests more leniency on first-time offenders, more job opportunities and support for ex-cons, and an end to the death penalty and other cruel punishements.

After meeting a man who's been there, who walked on the other side of law and order, after getting to know, respect, and like the man, it's hard to argue with that conclusion. Those behind bars are people, not animals, machines, or rocks. And let's face it, in recent years our prison and police system has only created more criminals, not to mention caused the deaths of hundreds of men and women.

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12 of 13 people found the following review helpful:
4.0 out of 5 stars How Burroughs Went Bad, June 2, 2000
This review is from: You Can't Win (Paperback)
Jack Black's tale of life as a small-time criminal in the turn-of-the-century West makes compelling reading today, even as it did for a young William Burroughs in the 1930s. Fans will read of the original Salt Chunk Mary, the Johnson family, the Sanctimonious Kid, and more, all characters so well-portrayed they must have been real. Black's prose is colorful without being overblown and he has quite an ear for dialogue (though his conversations with Chinese people are painful to read). Deeply sympathetic with the burglars, safecrackers, bunco men, and others who were his family for years, he shows most of them to have been honorable in their way, inspiring much of Burroughs' Western mythology in the process. Though he eventually settled down into a more secure life in San Francisco, Jack Black's heart belonged in the jungles outside town.
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8 of 8 people found the following review helpful:
4.0 out of 5 stars Yeggs, Gay Cats and Bindle Stiffs, June 6, 2001
By 
Chas Edwards (San Francisco, CA USA) - See all my reviews
This review is from: You Can't Win (Paperback)
Among other things, Black's 1926 autobiography is a dictionary of the gangster-hobo lexicon of the 1880s and 90s. Black and his colleagues blow open safes with "dan," then throw back "mickies of Dr Hall" and eat chicken "mulligans" around campfires at "bum conventions." That is, after they clear out the "gay cats" and "scissor bills."

It's also a thoroughly wonderful read. "You Can't Win" tells the life-story of Jack Black, who at sixteen leaves home heading "westbound in search of adventure," which he finds, along with a band of outlaw friends, frequent stints in jail, and a gripping addiction to opium. Black hypnotized me with his exploits on the road and in prison, tales that are part how-to's on house burglary, part nail-biting crime stories, part insider's critique of the criminal justice system. Black presents a detailed portrait of a bygone American West, where a small-town quaintness juxtaposes with the rough-and-tumble lawlessness of frontier mining culture. It's a time of transition in America, and Black's narrative captures both the innocence and the sophistication. Some scenes I imagined in sepia tones: Black breaks out of rickety jails with a pocketknife and exchanges unreliable paper money for gold. But as Black runs an opium ring from inside a San Francisco prison and orchestrates a mob murder of a double-crossing ex-girlfriend, I realized Black's world has plenty in common with our contemporary one.

Looking a little deeper, though, I had doubts about the reliability of Black as a narrator. I suppose memoirs, autobiographies and histories are by necessity narratives that select and omit details, and assemble countless events into a few hundred pages with a coherent plot and moral. But it's the autobiographer's challenge to win readers to his or her version of the story by eliciting our pathos and gaining our trust. Early in the book, Black succeeds completely. His direct, plain-speaking confessional introduces the ethical code of the Johnson Family, a fraternity of safe-cracking and house-robbing "yeggs" who treat their livelihood as a professional guild. Black's unfaltering commitment to the code and this community won my respect and admiration.

But at some point I became aware of glaring omissions that interrupted the narrative continuity and unseated my wholehearted trust. The book chronicles 35 years of Black's adventures, many of which take place in mining towns, skid-row bars and gambling halls, so it's not terribly surprising how few women characters make an appearance. But his relationship with one who does, Irish Annie, drew my attention to the question of authorial reliability. Annie's a prostitute whom he helps out of jam in Chicago. Later they meet again in Canada and Black lives in her brothel, content to let everyone think he's "Annie's protector and the man about the place," but he denies any sort of romantic relationship. Then Annie surfaces a third time: "a scorned woman" who takes her revenge corroborating a story that puts Black back in jail. Whether or not their relationship was more intimate than Black admits, I began to wonder what key details, what important adventures, didn't make the "autobiography." When Black recounts Annie's murder by a friend of his, he suggests this unnamed member of the Johnson Family decided to kill Annie on his own, an independent retaliation for her breach of the underworld creed. I suspected, however, that Black's role in the crime was more direct, and his storytelling had become less so.

Nonetheless, "You Can't Win" is a captivating and lyrical adventure story. It's written with the pace, diction and style of the best hard-boiled crime novels of its own era. And it has a voyeuristic appeal as powerful as contemporary gangster tales like Monster Kody Scott's "Monster: The Autobiography of an LA Gang Member" or Richard Price's "Clockers." Like "Monster," in fact, "You Can't Win" has the added pleasure of a book that sparks your thinking about narrative devices, truthfulness and the purpose of autobiography.

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11 of 12 people found the following review helpful:
5.0 out of 5 stars Jack Black was an unreconstructed yegg, and a real Johnson, November 17, 2006
This review is from: You Can't Win (Paperback)
An amazing little autobiography of a criminal from a forgotten time in american history. Jack Black was a burgler, safe-cracker, highwayman and petty thief from the late 1800s to early 1900s. His autobiography gives an amazing view to the underworld of those days; from the train-hopping Johnsons, bums and Yeggs of the hoboe community, to the chinese Opium houses, to the riotous wine-stews, to the straitjacket weilding jailors, to the characters; such as the righteous amazonian fence "Salt Chunk Mary" or the polished, erudite, ultra-smooth burgler "The Sanctimonious Kid." Heady stuff. And true to boot. I have a soft spot for criminal autobiographies of earlier eras. Of all the ones I've reviewed (or read in general), this one is far and away the most compelling. The world Jack Black evokes for us is radically different from anything we've ever heard of before. It is old world. It is modern. There is an entirely foreign and very complete kind of slang, intensely satisfying as a cultural object in itself. Jack Black himself was an amazing writer; his characterizations were powerful and full of flesh.
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6 of 6 people found the following review helpful:
5.0 out of 5 stars BEWARE: DON'T BUY THE INCOMPLETE PIRATED VERSION OF THIS BOOK BY BNPUBLISHING., August 29, 2009
By 
This review is from: You Can't Win (Paperback)
This edition of You Can't Win is the edition I did in 2001 for NABAT Books/AK Press and STILL IN PRINT. Bnpublishing ripped out the introduction by William Burroughs, the article from Harper's Magazine that Jack Black wrote about crime and prisons that I added, and my afterword, and republished it as their book. They didn't change the layout, typeface or anything else so for example their version starts with page 15. Don't buy this ripped off version !! Buy the complete and much more attractive version by NABAT/AK Press !! Oh yeah. It truly is a splendid book, kind of a bible of alienated outsiderdom. (I posted this review at the bnpublishing version of You Can't Win. I see it can now be found at the Nabat/AK Press version too. That's the version you should get: You Can't Win
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6 of 6 people found the following review helpful:
5.0 out of 5 stars Jack Black is a fascinating and utterly unforgettable book., February 28, 1999
By A Customer
This review is from: You Can't Win (Paperback)
From train tracks to opium dens, and finally to the stability of a job at the San Francisco Public Library, Jack Black writes a very personal account of adventure, hardship, loneliness, and longing. I absolutely loved this book. Black is a wonderfully interesting person, and his story is like none that I have ever found anywhere else--the story of a hobo in the early 1900's, who steals, does drugs, lives like a bum, rides the trains, and eventually decides he's had enough, settling down to a more conventional lifestyle.

He is the kind of person you want to meet and have a beer with. When the book was over I lent it to every person I cared about and they all loved it too.

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4 of 4 people found the following review helpful:
5.0 out of 5 stars A simple account of a life, April 4, 2001
By 
Andrew Suber (Terlingua, TX United States) - See all my reviews
This review is from: You Can't Win (Paperback)
Hard. Unforgiving. Undeniably American.

First the good news: this is a harrowing story of a misspent life from the man who chose to waste it. He is brutally honest; a better writer would have excluded the coarse sentimentality here. However, that would make this a false document or impair its ability to stir your emotions. I admire this man greatly. He is a hardened criminal who loves books and easy money. He describes, in great detail, the allure of crime in a simple, direct style.

The bad news: this man is not a professional writer. If you are looking for a distinctive prose style or something that will fit into a literary cubbyhole, this is not the book for you. This is not a beat book. This is not an avante-garde book. This is a book written by a man who has lived a long and puzzling life with comparatively little formal education. It is probably closest to "Papillon" or any other true life story.

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3 of 3 people found the following review helpful:
5.0 out of 5 stars A Great Book, May 24, 2006
This review is from: You Can't Win (Paperback)
Simply one of the most interesting and capitvating books I have read in a long time. The extra information at the end is great. A real slice of life that we 21st century-types are completely disconnected from. There is a great deal to learn from this book.
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3 of 3 people found the following review helpful:
5.0 out of 5 stars More than just a Burroughs influence, September 7, 1999
By A Customer
This review is from: You Can't Win (Paperback)
This is a bright engaging book that deserves wider audience than its current incarnation as an influence on Burroughs is giving it. The hobo-thief underworld of an American past is truly alive in these pages, and it made me wistful and meloncholy for times and places I'll never know. I want to stop at the hobo junctions of Montana and Idaho from this true-life tale, but I'm afraid of what I'd find there today.
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You Can't Win
You Can't Win by Jack Black (Paperback - June 23, 2007)
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