by Jack Black
This is probably the first instance of Goodreads suggesting a book that I both never heard of and got super excited upon seeing it on my suggestions feed. I initially wondered why I should care about something written by Jack Black. (No offense to the man, but he doesn’t strike me as an author of literature that would be up my alley.) Naturally, I looked closer, and it wasn’t that Jack Black––which I’m quick to suggest when describing the book to others. This Jack Black was a freight-hopping hobo, a highwayman, prowler, a safe-cracking hop junky who found his way in and out of jail at the turn of the 20th century, and You Can’t Win is his memoir. And, seeing that You Can’t Win greatly influenced William Burroughs’ Junky, I figured it would be a great thing to inspect before actually reading through the latter book.
I’m happy to say that You Can’t Win successfully lived up to all my expectations going into it. Despite everything presumably being grounded in fact, Black’s memoir reads like a work of fiction, a great work of fiction, in fact. The many anecdotes peppered throughout kept me interested, made me want to find out what happens, what troubles our anti-hero gets himself into, and wanting to see him succeed despite his shady activities. The thing is, Black was a voracious reader––apparently even reading through the entirety of the Encyclopedia Britannica three times during his various prison stays––very well-spoken, and portrayed himself as having a very strong character, (in that criminal underground sort of way,) all of which came together to shape him into a compelling individual as I read. His storytelling is also quite strong, arguably on par with many masters of literature, often very clearly portraying the beauty that existed within the ugly underworld Black submerged himself into or very effectively evoking sadness as he recollects his life. Top everything off with some very mature discussions surrounding the notion of effective punishment and the severe problems with the then-modern prison system and You Can’t Win crosses over into the realm of excellent memoirs, where the author doesn’t just tell you what he’s been through, but also gleans something useful or profound from the exercise.
So it’s a bit of a tragedy that You Can’t Win seems to have fallen off of most readers’ radar in modern times, but it’s absolutely worth the read, and I’ll certainly be recommending it every chance I get.