You Can’t Win: By Jack Black, 279 pgs. By Katie Dunne

Apr 13, 2011

Jack Black’s memoir, You Can’t Win, is an exciting story of a life of crime in late 19th century America. But there’s something else in it, something beyond that. It’s deeply personal but not in an effusive, hyperbolic way. It’s straightforward and honest. Black’s cards are laid out on the table without sentimentality. His style of writing is often compared to Bukowski, but, again, the similarities go further. They both share an innocence in the face of—and in spite of—the grotesque, cruel, and outrageous world around them. Though he recounts stories of terrible abuse in prison and it is hinted that his disappearance in 1932 was the result of suicide, he seems to be eternally unjaded. If he were to tell you in the afterlife the story of tying weights to his feet and jumping in the New York Harbor, he’d be just as evenhanded and forthright as he would be explaining to you how to case a neighborhood or who to go to when trying to get rid of stolen valuables.

It’s fascinating to learn the ins and outs of life as a criminal during the early days of America, doubly so because Black is haplessly stumbling into his life along with us. As a sixteen year old he learns how abusive and unconcerned the justice system is when he’s falsely arrested and swept into the jail without any chance to defend himself.

But times like this served his education well. He learns quickly because he’s a perceptive student. He tells us, “Whatever knowledge I have was gleaned by looking and listening, and it is much more accurate than any I could have got by asking impertinent and close-up questions. Your best friend would give you a surly answer if you were to ask him the time of day an hour after his watch had been stolen.”

Actions, of course, are much more powerful than words, and his attitude applies not just to the people around him but his own innate sense of loyalty and square-ness. The “wrong” people (as he calls the marginal people: thieves and bums) may not be considered honorable, but their code of loyalty is deeply impressive to him. The justice system, police officers, judges—the “right” people—are corrupt and jaded. He’s falsely arrested and dismissed without any consideration multiple times. He takes it in stride because that’s what has been dealt to him. The “wrong” people are the first to show him appreciation and to generously give when they could easily take advantage of a young naïve kid.

In telling the story of one of his many escapes from the law he writes, “I will not say there is honor among thieves, but I maintain that the thieves I knew had something that served as a good substitute for honor. On a propitious night he cut the window bars. I was too weak to pull myself up to the window, and he had to reach in, lift me bodily, and drop me on the ground outside.” Despite his cut and dry language, there are moments like this, and also in his discussion of his reformation, which are deeply moving. You Can’t Win is an inspiring read, a book to shore up against the constant embattlement of cynicism and jadedness. –Katie Dunne (AK Press,

PO Box 40682, SF, CA)

Thankful Bits is supported and made possible, in part, by grants from the following organizations.
Any findings, opinions, or conclusions contained herein are not necessarily those of our grantors.