You Can't Win (2026) is a Western film that follows the true-crime story of legendary outlaw Jack Black, whose 1926 memoir became an unlikely bestseller upon its release and later inspired generations of counter-cultural writing. Currently, you can watch You Can't Win on Amazon Video, Fandango At Home. Streaming availability may vary by country and platform over time. It has a user rating of 5.0 out of 10 from 7 votes. Fans of western movies may also want to explore similar titles below.