A review of You Can’t Win by Jack Black

Reviewed by Paul Kane

You Can’t Win
by Jack Black
AK Press/Nabat
January 2000, Paperback: 340 pages, ISBN-13: 978-1902593029

Jack Black’s autobiography, originally published in 1926, was apparently William Burroughs’ favourite book – Denton Welch was his favourite writer, by the way, so there is perhaps a little bit of a contradiction here – and he provides an appreciative foreword to the AK Press edition of You Can’t WinOn even a first reading, it is easy to see why Burroughs would admire the book: Black was an outsider, a criminal and an opium addict, and he presents a compelling (and cynical) insider’s view of the justice system of the time. And for this last alone, the book is a valuable document: a criminal outsider of intelligence pretty much tells it like it was. More crucially though, there is often a sense, as you read, that Black’s is a voice we weren’t meant to hear – at least not in this form. For Jack Black isn’t a monster; he comes across as being (at the end, at any rate) a wise and compassionate man.

A large part of the charm of You Can’t Win is that it reads like the hard-boiled American fiction of the ‘20s; like Hammett or one of the other Black Mask boys. Chapter 20, in particular, is a superbly told story: an account of a payroll robbery and its fallout that pushes all the right buttons. Like many of Black’s adventures (or at least like those recounted here), it does not end well. Downbeat doesn’t do it justice.

Throughout, the writing has great immediacy and the same sort of authenticity with regard to the criminal life as the first few chapters of Edward Bunker’s later No Beast So Fierce. This is so whether Black is describing dodging railroad bulls and jumping on boxcars, getting picked up for vagrancy or winding up in a jailhouse where “a coloured woman was singing a mournful dirge about ‘That Bad Stackalee’”. Many scenes bring to mind images from old American films: a lost world, but one we’ve seen or seen imagined.

We follow Black’s life from the 1890s to about the mid-1920s. He is attracted to crime as a kid of 14, after reading tales of Jesse James and others, and at first it is a life of adventure and excitement. Later, as he becomes a “yegg” (a travelling thief), he comes to see crime as a game or sport: there are codes and rules, smart plays and foolish moves, allies and opponents. At the end, after opium addiction (“opium, the Judas of drugs, that kisses and betrays, had a good grip on me,” Jack writes at one point) and time spent in Folsom, Alcatraz, San Quentin and other prisons, he arrives at the pessimism of his title: you can’t win. Crime doesn’t pay. Still, he went to hell in his own way, which is the best any of us can hope for.

There are some extras here, to add to the Burroughs foreword. An afterword by Bruno Ruhland gives some further background of Jack Black’s life; and Ruhland’s account of the social reformer Fremont Older is interesting too. There is also an article by Black about prison reform: “What’s Wrong with the Right People?”.

To sum up: this is a memorable book and was an influential one too, for the Beats especially (“on the road” is a phrase that recurs throughout; Kerouac seems to have palmed it from here). It is that rare thing: a cult book that lives up to its reputation. Its take-home message: the world is a tool for self-discovery; not at all bad for an autobiography.

About the reviewer:Paul Kane lives and works in Manchester, England. He welcomes responses to his reviews and you can reach him at ludic@europe.com

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