Goodreads helps you keep track of books you want to read.
Start by marking “You Can't Win” as Want to Read:
You Can't Win
Enlarge cover
Rate this book
Clear rating
Open Preview

You Can't Win

4.35  ·  Rating details ·  3,015 ratings  ·  349 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)
More Details... edit details

Friend Reviews

To see what your friends thought of this book, please sign up.

Reader Q&A

To ask other readers questions about You Can't Win, please sign up.

Be the first to ask a question about You Can't Win

Community Reviews

Showing 1-30
4.35  · 
Rating details
 ·  3,015 ratings  ·  349 reviews

More filters
Sort order
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
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 an
Jan 04, 2012 rated it liked it
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
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
May 09, 2018 rated it it was amazing
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
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
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
Jul 16, 2012 rated it really liked it
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
Jan 12, 2015 added it
Shelves: memoir
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
Nov 27, 2007 rated it really liked it
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
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
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
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.
Aug 08, 2007 rated it it was amazing
Shelves: 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.
May 02, 2015 rated it it was amazing
What an immensely tough life to have lead. Reading books from this era of life never ails to enthrall me. And specifically learning about hobos and the like, crime and the lower classes of this era is fully satiated from this read. What a point in history!
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...
Jakub Kratochvil
Práskač je zítřka lidský rod!

Nemáte šanci je najkrajšia kniha, akú som minulý rok čítal. Je z tých prežitých, nie vykonštruovaných. Jack Black (1871-1932) sa tridsať rokov potuloval západom USA, vykrádal pošty a banky. Z tých tridsiatich rokov strávil polovicu v amerických a kanadských väzeniach.

Keby svoj život nespísal, bol by to len dobrodružný život bezvýznamného zlodejíčka závislého na ópiu z čínskych práčovní. Ale on ho spísal a na mnohé si pospomínal. Nie len na to, čo sa stalo, na spôsoby
Julien Rilzel
Apr 29, 2019 rated it really liked it  ·  review of another edition
« Ma vanité juvénile, cette confiance excessive qui naît de l'ignorance, me soufflait que je pouvais gagner à un jeu où personne ne gagne. »

Terriblement addictif. Les mémoires de Jack Black sont à la fois une incroyable histoire, truffée d'adrénaline, d'échec, de succès volatiles, de conseils, avertissements. On lit stupéfait, accro. Mais il sont à la fois un repentir, un deuil, un regret, et aussi une réflexion sur le milieu carcéral, sa brutalité et sa capacité à endiguer toute chance de rédem
Paul Ataua
Apr 14, 2018 rated it liked it
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 emoti ...more
Jan 27, 2012 rated it it was ok
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
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
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
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.
Jul 09, 2008 rated it it was amazing
Recommends it for: William S. Burroughs lunatics
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!
Oct 08, 2013 rated it really liked it
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
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
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.
Oct 15, 2008 rated it really liked it
Shelves: real-talk
The way it kind of turns into a prison reform pamphlet toward the end is a little weird, but then again that's where they guy spent about a third of his life so, y'know, it's cool. I'm not gonna' sweat it.
« previous 1 3 4 5 6 7 8 9 next »

Readers also enjoyed

  • Beggars of Life
  • Out of the Night: The Memoir of Richard Julius Herman Krebs alias Jan Valtin
  • Sister of The Road: The Autobiography of Boxcar Bertha - as told to Dr. Ben Reitman
  • Education of a Felon
  • Bad: The Autobiography of James Carr
  • Memoirs
  • Last Words: The Final Journals
  • Hobo
  • Call Me Burroughs: A Life
  • "Yellow Kid" Weil: The Autobiography of America's Master Swindler
  • Prison Memoirs of an Anarchist
  • Government
  • The Spring of My Life and Selected Haiku
  • I Was Looking for a Street
  • On the Lower Frequencies
  • Slackjaw
  • Wobblies! A Graphic History of the Industrial Workers of the World
  • Just Enough Liebling: Classic Work by the Legendary New Yorker Writer
See similar books…
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
No trivia or quizzes yet. Add some now »
“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
More quotes…