You Can't Win
17/02/2026
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.
Movie Information
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
Ted Rooney
as Jack's Father
Skyler Verity
as Young Jack
Brandon E. Jackson
as Prison Guard
Charles Baker
as Fremont Older
Rusty Tennant
as Depot Policeman
Chris LeBlanc
as Corbett
Robert Zorn
as Jungle Bum
William Warren Ward
as Jungle Bum
Earl Alexander
as Jungle Bum
Ron Lampman
as Jungle Bum
Rob Finney
as Jungle Bum
Art Hickman
as Jungle Bum / Pharmacist
Ken Clark
as Jungle Bum
Tim Henderson
as Jungle Bum
Robert Blanche
as Cy
Henry Mark
as Chew Chee
Alex Terzieff
as Work Crew Boss
Todd Lagestee
as Work Crew Guard
Louisa Krause
as Irish Annie
Ron Otis
as Hotel Detective
John Paulsen
as Junkie Husband
Kathy Hsieh
as Junkie Wife
Jim Hamerlinck
as Goldtooth
James Lapan
as Station Agent
Stella Diaz
as Station Agent's Wife
Mark Fullerton
as Canadian Constable
Scott
as Murphey
Anatol Yusef
as Dirty Dick
Anthony A. Kung
as Opium Den Pickpocket
Alexis Scarff
as Ghost Mother
Wesley Scarff
as Baby Jack
Kori Ennis
as Salon Patron
David Beck
as Salon Patron
