You Can't Win is a book I've wanted to read for a long time now, one that ever since I saw the title and cover of, I knew I had to read, with the fact that it was a major inspiration to the beat generation authors (most notably Burroughs) as another key point as to why. The best way to describe this is as proto-On the Road. In a sense, it's that same sort of book about chasing life and finding meaning, yet You Can't Win exchanges the out-in-nature drive-by-car stop-and-get-a-milkshake feel of On the Road with this harsh and oppressive atmosphere. The second half of the book is greater than its first, with Black talking more about his personal philosophies. The title shows Black's state of mind during the period of his life where he was a burglar- life is a game. You can't win.
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