Watch You Can't Win (2026) Official Trailer
5 / 10 IMDb February 17, 2026 2h 19m
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.
Director
Runtime
2h 19m
Release Date
February 17, 2026
Genre
Western
Status
Released
Languages
English
Country
United States of America
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
No photo
Jenni Bradstreet
as Chinese Sleeper
No photo
Jim Chow
as Chinese Sleeper
No photo
Tony Lao
as Chinese Sleeper
No photo
David Leong
as Chinese Sleeper
No photo
Hutch Stellick
as Boy Jack
Ted Rooney
as Jack's Father
Skyler Verity
as Young Jack
Brandon E. Jackson
as Prison Guard
No photo
Charles Baker
as Fremont Older
Rusty Tennant
as Depot Policeman
Production Companies
Photus Films
You Can't Win Official Trailer 2026
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