Jack Black (1) (1871–)

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 show more 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 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 show more 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. show less

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 show more 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. 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

I'm giving You Can't Win 4.5 stars placing it on the "cult classic" category because almost 100 years after publication it's still in print, there is even a movie version coming out this year (2015). It was also an influential favorite with Beat writers including William S. Burroughs who emulated book's style and stories in his 1953 Junkie.

Jack Black was born in 1871, and the period the book mostly describes is from about 1887 to 1900, when Jack was in his teens and twenties at the height show more of his adventures. The country was in a funk, crime was rampant, just about everything was legal including opium, industrialization was changing things but social welfare had not yet arrived. There were still hints of the Old West - Civil War vets bumming around, old Indians. Cars were not yet widely used and so everything revolved around trains. This is that world seen from the view of a hobo, tramp, yegg, thief. We learn the cant of the outcast, criminals and drifters circulating around the Western USA and Canada, and most of all the stories and adventures of Jack Black in and out of prison. A great piece of first person history and adventure. It's tough to stomach his complete disregard for his actions but does offer some insight into the mind of the criminal who can juggle the contradiction of sympathizing with his mark in order to make the score, and yet not caring about the misery caused.

He apparently wrote the book in collaboration with Rose Wilder Lane of Little House on the Prairie fame. She also ghost wrote Jack's articles for Fremont Older, editor of the San Francisco Bulletin, advocating for better prison conditions. And Lane was a friend of Ayn Rand and may have coined the term "libertarian" (in the modern sense). Lane wrote other biographies under her real name. I read her book on Henry Ford, one of the first bios on Ford ever written. It was criticized at the time for stretching the truth though it was a ripping good story she clearly had an ideological bent towards people who are self-reliant, mythologizing them like her friend Ayn Rand later would. show less