You Can't Win

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 gut page after page. A real stand-up guy that took the hard road; riding the rails, friend to cultural lepers, a brilliant and honest thief. He makes no excuses for himself. He lays his tale for good or bad toward the reader with complete grace. show more Jack has a cynicism and wit that would resonate with most anyone but it is really his mercy and kindness that turn the book into something remarkable. So, if you would, anyone...just get this book. You won't regret it and then get a copy for someone you love. show less

Smiler - “Kid, I’ll never try to rob another Mormon. I’ll go to work first.”

The author, Salt Chunk Mary, the Sanctimonious Kid (Sanc), Civil War veterans and all manner of ’yeggs’, vags, bums, winos, and ‘hypos’ fill this book with a cornucopia of colorful characters! Heck, even Bat Masterson is in here! And the 1906 earthquake in San Francisco! Black is a thief, albeit not a very lucky one, and his travels across the U.S.A. and Canada, and his travels through the jail cells of both countries, are quite an adventure to read about! He describes everything with great detail, including his heroin addiction, and he even gives his opinions on prison reform and ways to improve the legal/justice system. But it's his adventures show more that make this such a good read, and one can see the impact this book, and those adventures, would have on future generations, especially Kerouac and the Beats. This almost reads like a thief's version of "On the Road"! I sure am glad I picked it up! show less

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 show more '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. show less

i have read two autobiographies in a row now, and they couldn't be more different--Chateaubriand and Jack Black! No, not that Jack Black. This is former criminal and hobo Jack Black, who published this book in 1926. Like Chateaubriand, he gives an incisive picture of his life and times. Of course, the milieu is a bit different. Chateaubriand has the French Revolution for a background, whereas Jack Black has hobo jungles, cheap hotels, and prison. Both write well, however, although in very different ways. Chateaubriand's work is a literary masterpiece. You Can't Win is a masterpiece of straightforward storytelling using the jargon of the times. Both authors were well read, actually. Chateaubriand seems to have read every book ever show more written. Black, mostly during his spells in prison, had lots of time to read as well, and even ended up as a newspaper librarian once he decided to go straight, a few years before publishing his autobiography. So, while you might not be quoting or underlining passages in Black's book for their literary quality, you'll certainly remembers his stories of his apprenticeship in crime from a series of colorful, criminal, but somehow admirable characters--some of whom meet very bad ends. The preparation for the crimes and the details of how they were committed is fascinating. Home burglaries took place while the victims were asleep, and since valuables such as wallets and jewelry were usually kept in the bedrooms, that's where the thief went. Even if it meant putting a hand under a sleeping victim's pillow to find the loot. Other heists are a bit simpler, but not usually. And so many things can go wrong, as we learn from this chronicle. Of course, Black ends up in jail or prison. Jails of all types and prisons of all types, including in Canada, where a good portion of the book takes place. We also get interesting pictures of Chicago, Kansas City, Salt Lake City, San Francisco, and other places. Criminals must travel. The book uses a few words to describe ethnicities that aren't politically correct, but Black doesn't seem to bear any animus to any race or creed. He goes out of his way to praise the Mormons he did time with, for instance (most of the polygamists) for their generosity in sharing everything they had. Black also attests to the honesty of Chinese. He spent quite a bit of time with them due to his hop (opium) habit, which is one of the interesting sub-plots of the book.

Anyway, I highly recommend this book, as I did the first part of Chateaubriand's Memoirs from Beyond the Grave. Unfortunately, there is no sequel by Black. He apparently died just six years after this book was published, a presumed suicide. Details are sketchy--he disappeared and is presumed to have taken his own life after coming to the point where he didn't feel like living any more. This readiness for death is also a trait he shares with Chateaubriand--who just kept on living even when he had little interest in doing so! show less

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 reviewers 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 the whole damn thing up (which I doubt very much). There are truth and value in his words, and it's quite an entertaining and show more informative read. show less

Memoirs of a career criminal from the early 20th century, written after a long jail stint as a warning to others. He cracked safes, pulled burglaries, and burned through several fortunes. The book is packed with colorful detail (much of it unverifiable). It hits three things I enjoy: heists, historical texture, and old-timey slang. Having The New Partridge Dictionary of Slang and Unconventional English nearby helped a lot.

Somewhere, buried in an article about something else, I saw an oblique reference to Jack Black’s 1926 memoir as a little known cult classic. Hooked. I’m a sucker for little known classics, so I had to read this one. A sort of cautionary tale replete with gentle sermonizing, it’s also a truly fascinating account of the incubation, life and reform of a professional drifter, hobo and petty career criminal. There’s an innocence (if that;s the right word) reading it now from the perspective of the 21st Century. Writing about his formative years, his education as a criminal, his many incarcerations and his eventual reform, Black’s memoir is a rapid, straight ahead read that holds the reader’s interest with his inside look at the show more criminal mind - though this criminal mind probably is more insightful than most.

It’s the details of his criminal activities that are riveting - the stick-ups and heists, especially the planning of them, the fencing, the house break-ins, the hotel knock-offs, the safe cracking - as well as his descriptions of the prison systems (of both Canada and the US) back in those years. And it’s the prison systems and the reforms that Black felt made sense that must have been the real impetus for this book. One can’t help but think of our current approach to ‘crime and punishment’ when Black talks his straight talk about what works, what doesn’t, and is mostly counter-productive.

Jack Black. From juvenile ‘delinquent’ to rail car hoppin’ hobo, to on the lam criminal, to brutalized inmate, to bottom of the barrel ‘hop-head’, to prison reform librarian….it’s all here, and though Black admits his failings, he makes no excuses for himself. The code of the criminal that is a large part of Black’s memoir, carries over to Black’s post-criminal life with a consistent code of dispassionate self-examination. Therein lies the respect that Black earns from the reader with his honesty.

It’s difficult to explain to a layman the pride of a professional thief. Nevertheless he must have pride or he would steal his clothes, beat his board bills, and borrow money with no thought of repaying it. He doesn’t do those things day after day, but day after day he takes chances and is proud that he can keep his end up and pay for the things he needs. All wrong, of course, but there it is. If I had brains enough to grease a griddle, I would have taken a hundred dollars from the boss Chinaman in the matter of Chew Chee and gone off somewhere, got a job, and tried to do the right thing by myself and others. But no, I was a journeyman; I had served a long and careful apprenticeship; professional pride - I don’t know what else to call it - would not permit me to take the Chinaman’s money for rescuing him from our common enemy, the law, and I went out to get money in my own way.

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.”

Of reforming the criminal, Black has lots to say about the penal system as it existed in the early decades of the 20th Century. And while the reform of that system may have been one of the prime motivators for the writing of this memoir, it’s in the area of responsibility and self reform that Black really is very clear and speaks from experience - whether it’s in kicking a drug habit or changing one’s criminal ways.

I had long realized that my every act was wrong and criminal; yet I never thought of changing my ways. After thinking it all over with all the clarity and logic and fairness I could command, I was convinced that nobody but myself was to blame, and that I had just drifted along from one thing to another until I was on the rocks. I hadn’t been forced into this life, and this predicament, by any set of circumstances or any power beyond my control. I had traveled along this road largely of my own free will, and it followed that I could get on the right road any time I willed it.

Somewhat dated in a quaint way, a period piece of sorts, it’s still refreshing for its honesty and candor. show less