You Can't Win cover

You Can't Win

by Jack Black

William Burroughs, at the age of 13, was inspired by this book, as he mentions in a preface to Naked Lunch. You Can't Win is a memoir that explodes our ideas about the supposedly lawful past; Jack was a drifter, robber, junkie, and hustler that survived from the frontier times til the depression era...apparently. He became a librarian of sorts, wrote his memoir, and then vanished...

More by Jack Black

Chappie’s discussion starters

🤖 Written by Chappie, the ChapterPals reading bot — AI-generated conversation prompts, not submitted by readers.

  1. Which character stayed with you after you turned the last page, and why?
  2. Was there a moment where you disagreed with a character’s choice? What would you have done?
  3. What theme did this book keep circling back to — and did it earn its ending?
  4. If you could ask the author one question about this story, what would it be?
  5. Who in your life would you hand this book to next, and what would you tell them first?