You Can't Win
by Jack Black · first published 1926
83% recommend17% neutral
Why HN recommends it
Jack Black's firsthand autobiography covers his life as a late 19th-century thief and safecracker, offering an entertaining and vivid look at hobo and criminal culture. It is free to read on Project Gutenberg.
Summarised by Claude from recommending comments
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...
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1. You Can't Win by Jack Black - autobiography of a late 19th century safecracker and general criminal - long enough ago for everything to be different, but the differences are still recognizable 2. Stalin - the Kremlin…
on “Ask HN: 2018 Summer Reading List?” ↗You Can't Win by Jack Black (1926) -- about crime and punishment Of Captain Misson by Daniel Defoe (1728) -- about Libertatia Drugs and Rights by Douglas N. Husak (1992) Forces of Habit: Drugs and the Making of…
on “Ask HN: What are the best unknown books you have read?” ↗…trooper and state prosecutor who was named commissioner a year ago. 'If the person had used some of that creativeness, he or she would not have ended up inside.'" I read (and re-read, and re-read) the book You Can't Win on recommendation of a HN user. It's about a thief from the late 1800s-early 1900s, and the crimes he and his thief buddies did were pretty creative. A lot of crime is more brute-force than clever, but…
on “Cartographers have been hiding illustrations inside Switzerland’s maps (2020)” ↗> You Can't Win It's pretty entertaining! And free to read for anyone interested: https://www.gutenberg.org/ebooks/69404
on “Cartographers have been hiding illustrations inside Switzerland’s maps (2020)” ↗…quite good, though I learned later that the author has quite a bit of controversy. - The Twentysomething Treatment – Meg Jay The book was good, her interviews on people's podcasts are even better. - You Can't Win – Jack Black Awesome HN recommendation, an autobiography of an early 1900s criminal. - The Starship and the Canoe – Kenneth Brower Another HN recommendation. A snapshot of the life of Freeman Dyson…
on “Ask HN: What did you read in 2025?” ↗…Jargon term meaning "a little further along or "downstream". To keep the random learning going, Chinook Jargon [1] is fascinating in itself. A few years ago someone on this site suggested a book called You Can't Win, an autobiography of a reformed hobo/thief/addict written in the 20s. It's fantastic, especially the audiobook version on Spotify. Googling now, I'm seeing it got a (poorly reviewed) movie adaptation…
on “Glacier Mice” ↗For anyone intrigued by this sort of thing - that is to say the ethics of hobo culture - I would highly recommend reading `You Can't Win'[1], the autobiographical account of Jack Black's train hoppin', bank robbin' life as a yegg. [1]: https://en.wikipedia.org/wiki/You_Can%27t_Win_(book)
on “The Hobo Ethical Code of 1889” ↗You Can't Win by Jack Black - autobiography of a small-time safecracker in the late 19th and early 20th century. Long enough ago for everything in life to be different, not long enough ago for everything in life to…
on “Ask HN: Books you read in 2018?” ↗I recently listened to the audiobook for You Can't Win, by reformed old-timey criminal Jack Black (published 1926). It was amazingly well written (the guy read thousands of books in prison), and showed the underworld in the US and Canada, including the "hop…
on “The Cocaine Files” ↗Some time ago I read You Can't Win[1], a 1926 memoir by a hobo-by-choice named Jack Black. He describes his life as a hobo in various cities (including SF!), and the picture he paints of the turn-of-the-century will be eerily familiar…
on “What I learned reporting in cities that take belongings from homeless people” ↗