Plot Summary
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.
Our Take
Expert, independent review by the HollyFlixHD Editorial Team
Analyzing cinematography, narrative pacing, and lead performances for You Can't Win. Writing review...
Full Cast & Characters
Michael Pitt
Jack Black
Ivan Martin
The Sanctimonious Kid
Will Patton
Foot and a Half George
Jeremy Allen White
Smiler
Hannah Marks
Julia
Charles Baker
Freemont Older
Julia Garner
Chicken
James Hong
Old Chinese Man
Rusty Schwimmer
Salt Chunk Mary
Nina Arianda
Mrs. Alexander
Jenni Bradstreet
Chinese Sleeper
Jim Chow
Chinese Sleeper
Director & Crew
Robinson Devor
Director
Official Trailer
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Frequently Asked Questions
Where can I watch You Can't Win online?
You Can't Win (2026) is available to stream on various platforms. You can also watch it online via our Watch Online button.
What is the TMDB rating of You Can't Win?
It has a TMDB rating of 4.9/10 based on 8 votes.
Who directed You Can't Win?
You Can't Win was directed by Robinson Devor and released in 2026.
How long is You Can't Win?
You Can't Win has a runtime of 2 hours and 19 minutes.
Movie Details
- Release Date
- 2026-02-17
- Status
- Released