by Jack Black
No, this memoir is not about Tenacious D, Nacho Libre, or Kung Fu Panda. The Jack Black writing this story was born in 1871 and this autobiography is about his time thieving, train hopping, cat burglar-ing, and escaping prisons up and down the West Coast.
Originally published in 1926, Jack Black throws in lots of old-timey slang from the hobo underworld, Wild West, and criminal classes and it’s fun to puzzle through the smattering of unfamiliar words and turns of phrase. For example, I loved the stories of his “apprenticeship” to the yegg (criminal) brotherhood in pre-1906 San Francisco.
I know I would have enjoyed reading You Can’t Win when I was in high school (if only for the bragging rights that I was reading William Burroughs‘ favorite book). Instead, I only discovered this book a few weeks ago when a friend recommended that I read it since Jack Black turned from his life of crime to become a San Francisco librarian (!!) in his later years. You Can’t Win is worth reading if only for the incredibly interesting and often overlooked perspective of a petty criminal on our local history.