You Can't Win
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.
Release Date:
2026-02-17
Runtime:
139 minutes
Movie Genres:
Directed by:
Written by:
Produced by:
Original Language:
Starring:
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 available
Jenni Bradstreet
as Chinese Sleeper
No photo available
Jim Chow
as Chinese Sleeper
No photo available
Tony Lao
as Chinese Sleeper
No photo available
David Leong
as Chinese Sleeper
No photo available
Hutch Stellick
as Boy Jack
Ted Rooney
as Jack's Father
Skyler Verity
as Young Jack
Brandon E. Jackson
as Prison Guard
No photo available
Charles Baker
as Fremont Older
Rusty Tennant
as Depot Policeman
Chris LeBlanc
as Corbett
No photo available
Robert Zorn
as Jungle Bum
No photo available
William Warren Ward
as Jungle Bum
No photo available
Earl Alexander
as Jungle Bum
No photo available
Ron Lampman
as Jungle Bum
No photo available
Rob Finney
as Jungle Bum
No photo available
Art Hickman
as Jungle Bum / Pharmacist
No photo available
Ken Clark
as Jungle Bum
No photo available
Tim Henderson
as Jungle Bum
Robert Blanche
as Cy