70% of “You Can’t Win”

I’m about 70% of the way done through “You Can’t Win” and I’m not 100% sure about finishing it. Here’s the thing: it’s a well written book, and it does a good job of telling its story. But there’s an underlying problem I’ll get to in a bit. 

I first heard of this book somewhere on Reddit, I think, where someone said it was a major influence on William S Burroughs. Having re-read Naked Lunch earlier in the year, I was intrigued. Burroughs did read the book, and according to my own ‘research’ (eg Googling and reading a couple of articles about it) it’s called ‘an influence on beat writers’. I see it, kinda. Jack Black, the author, presents everything with a fairly neutral point of view. The fact that he’s a thief isn’t something that’s presented with any moral center— it just is, and while Black has a moral code of sorts, that code doesn’t extend to ‘don’t steal’. Black never justifies or gives excuses for his profession; though he does recognize he’s operating outside societal norms, and the book periodically dips into the various ways in which thieves view each other and their victims. These were the parts I found the most interesting— Black argues that a good thief feels some sort of empathy for his victims; that a good thief just takes valuables in a minimally intrusive way out of some sort of respect for the person he’s stealing from. 

Unfortunately, at least for me, Black spends a lot of time effectively telling the same story over and over: “I went here. I stole some stuff. It worked!” Or “I went here. I stole some stuff. It didn’t work, and I was caught!” Individually, these are great stories— Black describing simply walking out of his own trial for robbery because he realized no one was stopping him is hilarious, and he writes about his craft with a certain sense of pride; it’s the writing of a person who genuinely enjoys his work, and frankly, his ability to spin a good yarn probably proved handy in it. 

But it gets to be fairly same-y. Black is the hero of his own narrative. Sure, he’s a scumbag, but he’s a scumbag with a code. Other thieves love him, as do hobos! He always repays his debts to other criminals! He’s a smart, quick study! And so on. After a while, it all begins to feel a bit Mary-sue-ish. I don’t think that’s his intent— the book was originally published serially, and I believe that’s at the root of it all; if you read it once a week, in short bursts, you have a series of arcs with a connecting thread, the kind of thing that might have benefitted from editing a bit more. 

It was a bestseller in its day, however— and apparently has recently been made into a film. I’ll likely finish it— I rarely get this far along in something without finishing it, even if I am skimming by the end. If my impressions change, I’ll make a note of it in a further entry, but for now, it’s been a bit of a slog for me. You may find yourself a bit more enraptured by it, and to its credit it gave me a window into a world that I hadn’t previously experienced, which is part of what we seek when we read in the first place. 

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