You Can't Win (2026)

Name: You Can't Win
Genre: Western
Released: 2026-02-17
Duration: 139 min
Cast: Michael Pitt, Ivan Martin, Will Patton, Jeremy Allen White, Hannah Marks

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.

Watch You Can't Win online

Released 2026-02-17 · 139 min · Western

Directed by Robinson Devor

Cast

Michael Pitt as Jack Black
Ivan Martin as The Sanctimonious Kid
Will Patton as Foot and a Half George
Jeremy Allen White as Smiler
Hannah Marks as Julia
Charles Baker as Freemont Older
Julia Garner as Chicken
James Hong as Old Chinese Man
Rusty Schwimmer as Salt Chunk Mary
Nina Arianda as Mrs. Alexander
Jenni Bradstreet as Chinese Sleeper
Jim Chow as Chinese Sleeper
Tony Lao as Chinese Sleeper
David Leong as Chinese Sleeper
Hutch Stellick as Boy Jack