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YOU CAN'T WIN, COMPLETE AND UNABRIDGED

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Originally published in 1926, ‘You Can't Win’ is an amazing autobiography of a criminal from a forgotten time in American history by Jack Black, a burglar, safe-cracker, highwayman, and petty thief.

The book recounts Black's adventures in the hobo underworld, freight-hopping around the western United States and Canada, with the bulk of incidents taking place from the late 1880s to around 1910. He narrates of becoming a thief, burglar, and member of the yegg (safe-cracking) subculture, exploring the topics of crime, criminal justice, vice, addictions, penology, and human folly from various viewpoints, from observer to consumer to supplier, and from victim to perpetrator.

It is a true lost masterpiece, one of the most legendary cult books ever published in America.

258 pages, Kindle Edition

First published January 1, 1926

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About the author

Jack Black

3 books91 followers
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 and the criminal justice system, hence the title of the book. Jack Black was writing from experience, having spent thirty years (fifteen of which were spent in various prisons) as a traveling criminal and offers tales of being a cross-country stick-up man, home burglar, petty thief, and opium fiend.

Jack Black is an essentially anonymous figure (even his actual name is uncertain) who is recognized through association with William S. Burroughs . Although his philosophy on life was especially influential to Burroughs, who associated with similar characters in his early adulthood and mirrored the style of You Can't Win with his first published book, Junkie, Black's writings also had a profound effect on the writings and lives of all the Beat Generation.

After his last spell in prison Jack Black became friends with wealthy patron Fremont Older and worked for Older's newspaper The San Francisco Call. He worked on his autobiography with Rose Wilder Lane and eventually composed essays and lectured throughout the country on prison reform. He was also rumored to have received a stipend of $150 dollars a week to draft a screenplay titled Salt Chunk Mary with co-author Bessie Beatty, based around the infamous vagabond ally and fence of the same name in You Can't Win. The play flopped, although he was able to attain some amount of popularity, which subsided quickly. He is believed to have committed suicide in 1932 by drowning, as he reportedly told his friends that if life got too grim, he would row out into New York Harbor and, with weights tied to his feet, drop overboard. In You Can't Win Black describes this state of mind as being "ready for the river."

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Displaying 1 - 30 of 516 reviews
Profile Image for James Thane.
Author 10 books7,071 followers
August 25, 2014
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 stolen goods, coping with the law and other such skills. He sometimes operated alone and sometimes with a partner, but he always considered himself an "honorable" thief who would never run out on a bill for his room and who would never think of betraying a friend.

Some of his best lessons were learned in the jails and prisons of the far West, both in the U.S. and in Canada, where he networked with other criminals and polished his skills. Black writes movingly of the conditions he suffered in some prisons, and later in life he would become an advocate of prison reform.

For much of his early life, spending time in confinement was simply part of the cost of doing business. He accepted it stoically, but until the very end, he never left prison a "reformed" man.

As often as not, it seems, his carefully planned jobs failed for one reason or other. In one instance, for example, he blew a safe only to use too much explosive. Instead of blowing the door open, the blast blew the door completely off, tipping the heavy safe over on its front side, and sealing the valuables away from Black as surely as if the safe's door had remained intact.

Black had spent a long time planning the job and was extremely depressed when it failed, not to mention virtually broke. A friend offered him a "straight" job washing dishes to tide him over, but Black refused, explaining his philosophy of life as follows: "[T]he thought of working to me was a foreign as the thought of burglary or robbery would be to a settled printer of plumber after ten years at his trade. I wasn't lazy or indolent. I knew there were lots of easier and safer ways of making a living, but they were the ways of other people, people I didn't know or understand, and didn't want to. I didn't call them suckers or saps because they were different and worked for a living. They represented society. Society represented law, order, discipline, punishment. Society was a machine geared to grind me to pieces. Society was an enemy. There was a high wall between me and society; a wall reared by myself, maybe--I wasn't sure. Anyway I wasn't going to crawl over the wall and join the enemy just because I had taken a few jolts of hard luck."

In the end, Black does "join the enemy," after a judge and the corrections system unexpectedly gives him a break he never expected and treats him humanely for the first time. This experience sets him on the straight and narrow and convinces him that a more enlightened justice system could deter a lot of men from lives of crime, rather than condemning them to such lives.

All in all, this is a very interesting and engrossing tale, and it's nice to know that a new generation of readers will now have a chance to enjoy it.
Profile Image for Chrissie.
2,811 reviews1,421 followers
August 27, 2020
This book is written by a reformed criminal known as Jack Black (1871-1932). He had been a homeless vagrant, a burglar and a thief, had cracked safes and had been sentenced to a penitentiary five times. He lived a life of liquor and prostitution and was addicted to both gambling and opium. Details specifying incidents of his life dating from the late 1880s to around 1910, taking place in western USA and Canada, are chronicled in this book.

Exactly how the burglaries, thefts, cracking of safes and prison escapes were planned and executed are meticulously described. How houses to be burglarized are chosen, how that which is stolen is hidden and then sold and how tracks are covered are all here. You could almost classify this as a theft and burglary handbook! It dumbfounds me how deeply people sleep; I am sure if a stranger were in my bedroom I would wake up. Dogs and kids are burglars’ worst enemies!

Being arrested, interrogated, tried and imprisoned are all covered. Social networking between burglars and train hopping too. Doing time in jails, versus prisons or penitentiaries are compared. Have YOU ever been straightjacketed? You will find out what that is like here.

Finally, declaring that he had never broken his word, Black promised that if helped he would not commit another crime. We learn how with the help of Judge Frank Dunne and San Francisco newspaperman Freemont Older, Black’s twenty-five-year prison sentenced was reduced to one year, how he kicked his addiction to opium and got a job. The message of the book being that trust and kindness breed further trust and kindness, that prisons breed brutality, violence and further criminality. What is advocated is a just and more lenient criminal justice system, humane treatment of prisoners, extended probation and payroll opportunities given to convicts.

I got a bit tired and fed up about hearing how best to commit crimes. This became tedious. We are even told what he recommends doing in a stick-up; he tells us what he did when it happened to him, and he was not bodily injured. I also find it strange that not a word is spoken of regret for the harm he caused others. He seems to have no misgivings. He states that what he has done is wrong, but he does not analyze his behavior on the basis of moral principles.

The book begins with a foreword by William S. Burroughs; it being his favorite book and influential on writers of the Beat Generation. The book has been compared to Jack London’s novel The Road.

The audiobook is very well narrated by Bernhard Setaro Clark. It is easy to follow, and the words spoken are clear and distinct.

I am glad I read the book because it gave me a glimpse into another human being’s existence. I experienced his life as he experienced it. It is made clear that his life of criminality had become a habit. A person can be stuck in criminality by habit and see no way out!
Profile Image for Brenda.
5,058 reviews3,007 followers
March 12, 2023
Originally published in 1926, this autobiography by Jack Black tells of his life from the young age of ten, when on the death of his mother, his father sent him to a school run by nuns, where he learned prayers and manners. But it slowly became all down hill from there. His life on the road, from around sixteen years of age, taught him a lot and he was included as one of the "bums", looked after by the experienced guys as they taught him all they knew. His first stint in prison terrified him, but when he was taken under the wing of a seasoned crim, he felt safe.

Jack Black spent most of his life in and out of various prisons, sometimes bettering the cops, but most times not. After his final stint behind bars, he became a reformed man, working for the The San Francisco Call under the patronage of Fremont Older.

You Can't Win is described as a masterpiece, and a cult book. My view is that it's a sad book about a young man who needed the love of a mother, was desperate for hugs and caring, until he became hardened, no longer needing those things, just needing the next fix, the next burglary, the next adrenalin rush. A true crime autobiography, I'm happy to recommend You Can't Win to fans of that genre.
Profile Image for Rod.
108 reviews57 followers
June 3, 2013
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 absolute truth as it happened or if there were some "stretchers," as Huck Finn would say, or even if he just made it all up out of whole cloth (not bloody likely). There is truth and value in his words, his prose is clear and true, and the book is both highly entertaining and highly edifying. A vivid portrayal of life in the hobo underworld of the late 19th and early 20th centuries, a must-read for lovers of "down and out" literature.

***UPDATE 06/02/2013***

Apparently there is going to be movie starring Michael Pitt sometime in 2013, with Will Patton as Foot-and-a-Half George (Yay, Will Patton!). To mark the occasion Feral House is releasing a new edition with illustrations by Joe Coleman and bonus material on July 16, 2013. I suppose I'll feel obligated to buy that when it comes out.

http://feralhouse.com/you-cant-win/
Profile Image for DeAnna.
63 reviews8 followers
May 16, 2014
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 fact that it humanizes criminals and illustrates the unexpected morality in criminal subculture in a way that most of the population isn't really used to is a good thing.
Profile Image for Hank.
9 reviews9 followers
January 5, 2012
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 dream. Well, one of us. The rest of us just barely got our feet wet. We got our feet wet a lot, and our packs got water-soaked and the book along with them. One friend read it and gave it to the next. He, too, then gave it to the next. But that next one was slow to read, so I nabbed it off of him (what do you expect? it's a book about a burglar!) and finished it off. It was in many soggy pieces when I got it and it was in a few more when I was done. Pittsburgh to Philly to NYC to Boston, Providence, New Haven and back to New York just in time to go to Richmond, Virginia where we took a gaggle of fellow tramps on a train to Rocky Mount, North Carolina -- and there we met the fourth of our original crew and he took us to Chapel Hill, NC where we all got rip-roaring drunk for four days and then got kicked out of somebody's house. Then we went back to Rocky Mount and back to Richmond and to Washington D.C. and back to Pittsburgh.

But this book. Burroughs's favorite (we know, we know). For some reason I thought it was about a hobo or a fellow tramp. It's not. It's about a burglar who happens to hop trains. I was disappointed when Jack Black recounted a tale of robbing honest, hard-working hobos of their pay. But as far as the enjoyment of this book, I can't let Black's moral failings bother me. It's a decent enough book, though I don't normally read autobiography. I read fiction and philosophy most of the time. Lately I've been reading everything about life on the road that I can, as I'm housed up for the winter. If you're interested in the hobo/tramp life, I recommend Jack London. I think it's interesting to compare London's and Black's separate experiences in prison -- London was certainly of a different temperament. I hope at some point to read W.H. Davies's "The Autobiography of a Supertramp."
Profile Image for iva°.
736 reviews110 followers
January 29, 2023
jack black, alias thomas callaghan, napisao je ovo memoarsko djelo nakon što je trideset godina proveo kao skitnica, provalnik, pljačkaš i uživatelj opijuma (od toga 15 godina na slobodi, a drugih 15 po zatvorima, između ostalima i u folsomu, alcatrazu i san quentinu). žario je i palio kanadom i amerikom između 1881. i 1912. da bi se potom skrasio, zaposlio u novinama te netragom nestao i 1932. proglašen umrlim (pretpostavlja se na samoubojstvo koje je znao natuknuti).

za čovjeka koji je proveo većinu svog života na ulici i po zatvorima, tekst je zapanjujuće jasan, svjež, duhovit, osmišljen, refleksivan, lucidan, a njegove crtice samokritike i nježnog upozorenja kriminalcima koji će ga čitati o sudbini koja ih vreba iza vrata suptilna je i dirljiva.

kratko se na početku osvrnuo na svoju polazišnu točku (smrt majke dok je bio malo dijete i život s ocem koji je odsutan i duhom i tijelom) te direktno prešao na srž onoga što želi ispričati: avanture, pljačke i općenito milje ondašnjih skitnica; tek na posljednje tri-četiri stranice kratko se dotiče života nakon posljednjeg izlaska iz zatvora. od 270 stranica knjige, na njih 250 bavi se svojim pljačkaškim pohodima, na koje je krenuo kao desetogodišnjak, a koji su mu u početku bili strast, radost i gušt, no s vremenom se pretvaraju u jedini oblik življenja koji poznaje i za kojeg je sposoban.

srest ćeš tu i njegove pitoreskne kompanjone legendarnih imena: dugoprstog texa, malog sveca, irsku annie, šepavog georgea te cijeli niz odvjetnika, sudaca i tužitelja, zatvorskih čuvara i mučitelja (u to doba još su u zatvorima bili aktualni bičevanje i mučenja luđačkom košuljom i vodom). piše iskreno i otvoreno, svjestan svog promašenog života, ne pravdajući se niti nalazeći opravdanja za svoj životni izbor. radio je ono što je volio, želio i jedino znao, pokušavajući svojim žrtvama nanijeti najmanju moguću štetu u takvim okolnostima, a svojom autobiografijom izložio je što znači biti skitnica i kriminalac koji je, kad je sve zbrojio i oduzeo, ostao na nuli.

"ali pomisao na zaposlenje bila mi je strana kao što je pomisao na pljačku ili grabež uglednom tiskaru ili vodoinstalateru s deset godina iskustva. nisam bio lijen ili indolentan, znao sam da postoji mnoštvo jednostavnijih i sigurnijih načina da čovjek zaradi za život, ali to su bili načini drugih ljudi, ljudi koje ja nisam poznavao ni razumio, a nisam ni htio. nisam ih nazivao budalama i bedacima zato što su bili drugačiji i zaradili za svoju plaću. oni su predstavljali društvo. društvo je predstavljalo zakon, red, disciplinu, kaznu. društvo je bilo stroj napravljen da mene samelje u dijelove. društvo mi je bilo neprijatelj. između mene i društva sterao se visoki zid, zid koji sam ja sam možda podigao - nisam bio siguran."

"znao sam da sam u krivu, ali sam ustrajao. ako i postoji nekakvo objašnjenje za to, onda je ono sljedeće: od dana kada sam otišao od svoga oca, moja udica je bačena, ili sam je sam bacio, među pokvarene ljude. nisam proveo ni sat vremena u društvu poštene osobe. živio sam okružen provalama, krađom, kriminalom. krađa mi je postala način razmišljanja. kuće su bile izgrađene kako bi se u njih provalilo, građani su bili tu da ih se opljačka, policajci da ih se izbjegava i mrzi, doušnici da ih se kažnjava, a lopovi da ih se njeguje i štiti. to je bio moj kodeks i kodeks mojih drugova. to je bio zrak koji sam disao. -ako živiš s vukovima, naučit ćeš zavijati."
Profile Image for Yair.
330 reviews100 followers
May 24, 2022
It's been a while since I've done a 'proper review' (however the hell that's defined) but this was requested so I figured why not?

Rather than waste time with the unnecessaries let me just say that this book is quite fantastic. Now, this already qualified 'quite fantastic' requires a few caveats, asterisks, modifiers, et freaking al. This is a dated text, very dated. Some might construe this datedness as problematic but, honestly, I would disagree; this is a book so contextually all over the place (problem of authorship, authenticity, what have you) that for it to be anything other, or less, than what it is would absolutely reek of the college educated editor when, for a text like this, that simply couldn't work.

Despite being billed as 'true' this story reads like fiction, in fact, to call this both a bildungsroman and even, god help me, picaresque (if that's to be taken in a gritty, all too turn of last century American way) is, to my mind, accurate. 'Jack Black' as a character does much but learns little, but this little builds over time into a considerable amount of hard earned wisdom, particularly American in its rough hewn and directly stated truth.

I very much recommend this work to anyone interested in true crime, history, biography, and honest, if very exaggerated and somewhat Romanticized, Yankee grit.
Profile Image for Kevin Farrell.
374 reviews6 followers
March 14, 2012
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 lot about the honor and friendship that he shared with others "on the road". Many times he would hop off a train and walk into a town with nothing but his shirt and someone who knew him would feed him and hand him some money - knowing he was good for it. He always paid them back as soon as he got his own money. He and others like him had "reputations" on the road with others like him.

Other reviewers don't see this book as much better than mediocre. I guess that depends on what you are looking for when you read it. It is not too often that you find a man who has done everything in life wrong who can also articulate his story this well.
Profile Image for Andrew.
2,254 reviews925 followers
Read
January 18, 2015
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 interest in the darker corners.
Profile Image for Jolie.
Author 1 book8 followers
May 10, 2018
I will probably always scramble for words to describe this epic. Though I can say for sure that it will be the first book I'm going to recommend to anyone, for the foreseeable future.

Frightening, surreal, very very real, heart breaking and shocking, adventurous and humorous - all with a moral lesson tucked away in the shadows of this underground while told in the voice of your older, kindly neighbor. Feelings and words are everywhere.

It wasn't until I reached the end that I noticed the text at the very bottom of the publication page: "Prisoners can receive this book by sending $10.00 to A.K. Press at the Oakland address noted above." A knot shot right to my throat and it's going to be a while before it goes away.
Profile Image for Andrea.
1,271 reviews96 followers
August 22, 2025
Awesome tales of robbery, opium addiction, prison, etc. I loved this book!
Profile Image for L'ours inculte.
465 reviews9 followers
May 28, 2019
L’an dernier, dans mon infinie bonté, j’ai offert des romans de la superbe collection Les grands animaux de chez Monsieur Toussaint Louverture. Évidemment, comme tout lecteur qui offre des livres, le cadeau fut suivi d’un « bon, et tu me les prêtes quand t’as fini hein ». Allez, avouez, on l’a tous fait, non ? Le premier à m’être tombé dans les mains est donc Personne ne gagne de Jack Black (non, pas ce ce Jack Black)

Personne ne gagne, donc, ce sont les mémoires d’un vagabond-voleur qui a arpenté un bon morceau d’Amérique du Nord à la fin du XIXe siècle et au début du XXe. C’est auto-biographique, le bouquin original est paru il y a presque 100 ans, et il fallait bien un Monsieur Toussaint Louverture pour nous ressortir ça de derrière les fagots pour l’emballer dans une classieuse couverture noire et argent. Le narrateur retrace sa vie sur les routes, entre cambriolages, combines, cavales et grosses fiesta de clodos. On découvre un personnage à la fois extraordinaire et humble, lucide sur ses erreurs et son époque, et sur ce qui l’a amené là où il est. En retraçant toute sa carrière, on croisera les personnages qui l’ont formé, accompagné, aidé, trahi. Mais on va surtout vivre une époque.

Le livre se passe dans une Amérique post-conquête de l’ouest, mais pas encore tout à fait apprivoisée pour autant. C’est fascinant de voir cette ambiance post-western, traversée par un personnage en marge, qui fréquente les hobos, les rois de l’arnaque et les cambrioleurs en tous genres. Il va profiter de systèmes judiciaires pas encore tout-à-fait mis en place et de l’immensité du territoire pour échapper aux autorités, et construire des plans avec ses complices. C’est très fun de voir ces bandes de voleurs avec leurs combines, mais aussi leur éthique, leur sens de l’honneur et leur solidarité. Les parias se serrent les coudes ou se grillent à vie. Pourtant Blacky n’échappera pas à la justice et ses épisodes d’incarcération vont devenir aussi une composante très importante du discours du roman. Mais ils seront surtout un témoin de l’époque, parfois aussi cru et poignant qu’un Meurtre à Alcatraz.

Pour un lecteur d’aujourd’hui, le livre a quelques défauts qu’on peut relever, comme ce texte massif qui mélange dialogues et narration sans vraiment aérer (sans doute un truc de l’époque). On note aussi une certaine répétitivité passé la moitié du roman, quand le protagoniste nous déballe plusieurs épisodes de cambriolages à la suite qui font un peu redondants. Mais pourtant l’atmosphère est fascinante, le cheminement de ce gamin qui rêve d’un costume gris et finit par faire péter des coffres à la dynamite, c’est un voyage grandiose plein de désillusions, d’erreurs et d’errements entre les coups foireux, l’opium et les salles de jeu. L’époque était pleine de possibilités, mais aussi cruelle et d’une certaine manière très arbitraire.

Comme d’habitude chez l’éditeur (du moins sur les trois romans que j’ai lus), Personne ne gagne est un livre atypique, fascinant, accompagné avec soin et présenté au lecteur comme un trésor. Pas parfait, mais il a une âme, un propos et une ambiance. Oui, non, c’est pas de la SFFF, je sais, je fais des infidélités à l’imaginaire.

http://ours-inculte.fr/personne-ne-ga...
Profile Image for Paul Ataua.
2,178 reviews281 followers
April 14, 2018
An interesting piece of social history following the story of someone living life on the road, living as a hobo, traveling the boxcars, and being drawn into the life of the petty criminal, slipping in and out of jail. Once you get over the social history part, the way hobos folded the clothes and placed their shoes when they slept, the meetings and information exchanges between different people on the road, the actual stories are pretty dull, and Jack Black does nothing to evoke tension or emotion. He tells everything, almost deadpan, as it happened, and as it happened it didn’t make unputdownable reading.
28 reviews1 follower
February 21, 2008
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.
Profile Image for Patrick O'Neil.
Author 9 books155 followers
May 26, 2010
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 sang huge praise for Fante, and then literally mimicked him. It's a little disappointing if you think about it. I have nothing but mad respect for both Bukowski and Burroughs. Growing up I thought they were amongst the most innovative writers of our time. Now I am left wondering if they had any originality at all? But then I still think their work amazing - so does it matter? Do all writers borrow? Is anything really original any more?

I think of my own writing and wonder if I too am liberating someone else's style? I haven't knowingly gone and taken anyone's style. Yet, I read a lot - do I do it without knowing? Is that how it happens? Every time I read a really great book I'm inspired to write - yet I'm usually writing something totally different.

Yet aside from all that, You Can't Win is a dark tale. There's a few discrepancies. But all in all it is an amazing read of one man's criminal journey.
Profile Image for Tosh.
Author 14 books777 followers
July 10, 2008
This is an actually a very amazing book. Written in the early 20th Century, William S. Burroughs took the 'voice' of this book and used it consistently through out his career. He admits that this was a blueprint to his own writing. But beyond that, "You Can't Win" is a great document of hobo life in the U.S. A truly classic book!
Profile Image for Corey Edwards.
26 reviews1 follower
December 30, 2021
"You Can't Win" is one of the best books I've read in years. Jack Black's autobiography (no, not THAT Jack Black) is fascinating, gritty, moving, funny, instructive, and eye opening in ways that most works of fiction can only dream of. Hobo, thief, killer, philosopher. A man of his times yet also well ahead of them. READ THIS BOOK!
41 reviews6 followers
December 4, 2013
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 opening few chapters. Black’s story is also a profoundly personal tale of caution. There are consequences to living your life by your own rules (even in the early 1900s). Black had highs. His skill at thieving enriched him for short periods and he enjoyed the passing pleasures of drug and drink and the fellowship of his fellow yeggs. But there were lows. He spent much of his life in jail, on the run or desperately poor and addicted to drugs.

You Can’t Win comes from a time that doesn’t exist any longer. We couldn’t drop off the radar any more than we could learn to fly on our own. The book isn’t a roadmap to our own Walden Pond, but it’s an interesting rumination on our own personal obligations to what is expected of us, our responsibilities to our fellows and our role in the grander order. Read this book.
Profile Image for Tentatively, Convenience.
Author 16 books245 followers
April 7, 2008
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 hobo jungles. I learned about the Johnson Family of good bums and thieves, with a code of conduct that made more sense to me than the arbitrary, hypocritical rules that were taken for granted as being "right" by my peers."

Exactly. As usual, getting a realistic insider's look of an illegal lifestyle is bound to be much more honest than a critical one written by an outsider. But what do I know? It cd all be bullshit. I take it for granted that it isn't though. I particularly liked Black's description of being stuck up himself as an older man. There're no heroics or daring macho behavior on his part. Even as a old hand himself he was still taken by surprise.
Profile Image for Tim.
200 reviews14 followers
March 17, 2014
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 hacks that are relevant to modern-day computer security.

For example, he encountered an uncrackable safe that was due to have a lucrative payroll stored in it. Instead of giving up, he disabled the safe so that nobody could use it. The payroll money was then stored in a less secure place.

Profile Image for Vaggelis.
61 reviews9 followers
June 6, 2022
Πολύ σημαντικό και υποτιμημένο βιβλίο!

Πρόκειται για την αυτοβιογραφία ενός κλέφτη /«φτωχοδιαβολου» με το όνομα Jack Black.

Ο συγγραφέας εξιστορεί με μεγάλη ακρίβεια τι τον έσπρωξε στην παρανομία και τι τον έθεσε εκτός. Έχει επίσης και πολύ ενδιαφέρουσες απόψεις για τον τρόπο λειτουργίας του «σωφρονιστικού συστήματος».

Περιγραφές διαρρήξεων , δικαστηρίων και φυλακών του προηγούμενου αιώνα γίνονται με αριστουργηματικό τρόπο αποδεικνύοντας ότι κανένας δεν γεννιέται εγκληματίας.

Όι επιλογές του συνέβαλαν στα σίγουρα για να φτάσει σε αυτό το σημείο ,όπως και η οικογένεια του,όμως μια κοινωνία που απλά τον αγνοεί και τον μειώνει πόση ευθύνη έχει;

4,5/5
Profile Image for Cwn_annwn_13.
510 reviews83 followers
September 10, 2020
I didn't expect to like this as much as I did. Having known so many criminals and jailbird bullshitters in my life I know that what comes out of the mouths of 95% of these people is not worth retaining or listening to. But this one really reeled me in and kept me interested the whole time. The gist of this book is Jack Black who was serial burglar/hobo/habitual criminal and eventual Opium addict in the late 1800s to well into the 1900s recounts his life, lifestyle, prison stints and various capers. Really entertaining stuff that takes you back to another time.
Profile Image for Dave Russell.
74 reviews131 followers
March 14, 2007
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.
Profile Image for Mike.
66 reviews11 followers
March 26, 2025
Wow. This book is amazing.

Written in the 1920s, it's a first-person memoir and autobiography of a criminal career spanning decades. Jack Black recounts the story of his upbringing by his father after his mother's death, to boarding school at a Catholic institution, to a loose-ends adolescence that drifted into criminality and stayed there. Hobo jungles and freight trains, but also bank jobs and burglaries. I don't want to spoil anything, but it's a fantastic story.

His reformation is even more compelling. I feel like I should have heard of this guy before. I never had. But I had heard of some of the folks who helped him after his life of crime. The scholars who produced the edition I read included biographical information and one excellent magazine piece he'd written, in addition to the book -- he was a real person.

I bought my copy at City Lights Books in San Francisco, where you'd expect to find this sort of volume. Best book I will read this year, for sure. You should get one, too.
Profile Image for William.
332 reviews9 followers
October 15, 2021
A delightful romp through the hobo underworld. Jack Black isn't an American hero but he is most definitely an American even though he was a British subject by way of Canada. It's all too confusing, but pedigree didn't matter so much in the wild days of the late 1800's. This book presents us with dichotomies and juxtapositions that are still prevelent to this day - Homeless camps outside of rich neighborhoods, punishment vs. reform, beans vs. pork. This is one of those books that could have been written at almost any time in our history. The essays at the end on criminal justice (written in 1929) are just as meaningful today as they were when they were written. All I can say is, the world needs more Salt Chunk Marys in it.
99 reviews
November 24, 2024
Amazing book. I could not get enough. Highly highly recommend.
The portrait of America in this period told so honestly is illuminating. I can't even begin to describe how exciting it is to hear about cat houses, Chinatown laundries, hobo conventions, riding the rails, the conditions at Folsom prison, etc. etc. etc. ad infinitum. It's a true treasure trove. I am furious that someone else has made this into a movie before me.
Profile Image for Frank McGirk.
867 reviews6 followers
January 13, 2021
A very interesting read(listen). A detailed, and believable, look at a life of crime in pre-turn of the century America. Besides the scams Black ran, the small historical bits about businesses being distrustful of paper money and the like gave the tale so needed flavor. Though it did have a consistent refrain about how someone working steadily would actually earn a better life than a life of crime, the tone really was dispassionate, which did add to the believability, but if it's a raucous read you're looking for, this isn't it.
Profile Image for Phoenix Ocean.
94 reviews
January 30, 2025
This is full of fascinating true stories about a time that seems quite far removed from our own, though it's only been about century since it was written. Jack Black has a delightfully playful narrative voice that still reads as completely sincere, especially in his descriptions of dear and usually departed friends. It's interesting to hear from someone who navigated the moral/ethical/legal codes of both the criminal underworld and more polite society.
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