You Can't Win
Synopsis
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.
Trailers, Teasers & Extra Featurettes
Official promotional previews, behind-the-scenes footage, and exclusive clips.
You Can't Win - Trailer
Type: Trailer • Published 2026-02-15
Top Cast
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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
Tony Lao
Chinese Sleeper
David Leong
Chinese Sleeper
Hutch Stellick
Boy Jack
Ted Rooney
Jack's Father
Skyler Verity
Young Jack
Brandon E. Jackson
Prison Guard
Release History & Theatrical Window
February 17, 2026
VOD & Digital Platforms
Key Information & Fast Facts
- Director
- Robinson Devor
- Screenplay & Story
- Charles Mudede, Robinson Devor, Barry Gifford, Michael Pitt
- Original Score
- Paul Matthew Moore
- Original Title
- You Can't Win
- Country of Origin
- United States of America
- Spoken Languages
- English
- Runtime
- 2h 19m
- Production Studios
- Photus Films
Creative Leadership & Key Crew
Robinson Devor
Charles Mudede, Robinson Devor, Barry Gifford, Michael Pitt
Paul Matthew Moore
Sean Kirby
Department Leadership Roster
Charles Mudede
Screenplay
Robinson Devor
Screenplay
Barry Gifford
Screenplay
Robinson Devor
Director
Michael Pitt
Screenplay
Sean Kirby
Director of Photography
Paul Matthew Moore
Original Music Composer
Production Stills & Gallery
Official cinematic photography and background stills for You Can't Win.
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Frequently Asked Questions About You Can't Win
Quick factual answers about cast, synopsis, director, box office, and release information.
What is You Can't Win about?
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.
Who directed You Can't Win?
You Can't Win was directed by Robinson Devor.
Who stars in You Can't Win?
The principal cast of You Can't Win includes Michael Pitt, Ivan Martin, Will Patton, Jeremy Allen White, Hannah Marks.
When was You Can't Win released and how long is it?
You Can't Win was released in 2026 with a total runtime of 2h 19m.
Who composed the musical score for You Can't Win?
The original motion picture soundtrack for You Can't Win was composed by Paul Matthew Moore.