You Can't Win
Robinson Devor2026-02-17
5.2
139 min
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.
Cast
| Name | Character | Team | |
|---|---|---|---|
 |
Michael Pitt | Jack Black | The Free Refills |
 |
Ivan Martin | The Sanctimonious Kid | Unowned |
 |
Will Patton | Foot and a Half George | Goutbreak |
 |
Jeremy Allen White | Smiler | Goutbreak |
 |
Hannah Marks | Julia | Unowned |
 |
Charles Baker | Freemont Older | Unowned |
 |
Julia Garner | Chicken | Zac E. Chan |
 |
James Hong | Old Chinese Man | Unowned |
 |
Rusty Schwimmer | Salt Chunk Mary | Unowned |
 |
Nina Arianda | Mrs. Alexander | Unowned |
 |
Jenni Bradstreet | Chinese Sleeper | Unowned |
|
Jim Chow | Chinese Sleeper | Unowned |
|
Tony Lao | Chinese Sleeper | Unowned |
|
David Leong | Chinese Sleeper | Unowned |
|
Hutch Stellick | Boy Jack | Unowned |
 |
Ted Rooney | Jack's Father | Unowned |
 |
Skyler Verity | Young Jack | Unowned |
 |
Brandon E. Jackson | Prison Guard | Unowned |
|
Charles Baker | Fremont Older | Unowned |
 |
Rusty Tennant | Depot Policeman | Unowned |
 |
Chris LeBlanc | Corbett | Unowned |
|
Robert Zorn | Jungle Bum | Unowned |
|
William Warren Ward | Jungle Bum | Unowned |
|
Earl Alexander | Jungle Bum | Unowned |
|
Ron Lampman | Jungle Bum | Unowned |
|
Rob Finney | Jungle Bum | Unowned |
|
Art Hickman | Jungle Bum / Pharmacist | Unowned |
|
Ken Clark | Jungle Bum | Unowned |
|
Tim Henderson | Jungle Bum | Unowned |
 |
Robert Blanche | Cy | Unowned |
|
Henry Mark | Chew Chee | Unowned |
|
Alex Terzieff | Work Crew Boss | Unowned |
|
Todd Lagestee | Work Crew Guard | Unowned |
 |
Louisa Krause | Irish Annie | Unowned |
|
Ron Otis | Hotel Detective | Unowned |
 |
John Paulsen | Junkie Husband | Unowned |
 |
Kathy Hsieh | Junkie Wife | Unowned |
|
Jim Hamerlinck | Goldtooth | Unowned |
|
James Lapan | Station Agent | Unowned |
|
Stella Diaz | Station Agent's Wife | Unowned |
|
Mark Fullerton | Canadian Constable | Unowned |
|
Scott | Murphey | Unowned |
 |
Anatol Yusef | Dirty Dick | Unowned |
 |
Anthony A. Kung | Opium Den Pickpocket | Unowned |
|
Alexis Scarff | Ghost Mother | Unowned |
|
Wesley Scarff | Baby Jack | Unowned |
|
Kori Ennis | Salon Patron | Unowned |
|
David Beck | Salon Patron | Unowned |