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  • You Can't Win
  • Drama
You Can't Win
Drama

The true-crime story of Jack Black, whose 1926 memoir became an unlikely bestseller upon its release and later inspired generations of counter-cultural writing.
Director
Writers
Jack Black (based on the novel by) | Robinson Devor (screenplay) | Barry Gifford (screenplay) | Charles Mudede (screenplay) | Michael Pitt (screenplay)
Cinematographer
Casting Directors
Susan Shopmaker | Heidi Walker (Seattle Casting)
Production Designer
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Status
Edit Post-Prod
Updated Feb 27, 2024

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Cast

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58 cast members
Name Known for
Michael Pitt
Jack Black Jack Black   See fewer
Will Patton
Foot and A Half George Foot and A Half George   See fewer
Charles Baker
Fremont Older Fremont Older   See fewer
Louisa Krause
Irish Annie Irish Annie   See fewer
Rusty Schwimmer
Salt Chunk Mary Salt Chunk Mary   See fewer
Anatol Yusef
Dirty Dick Dirty Dick   See fewer
Ted Rooney
Jack's Father Jack's Father   See fewer
Ivan Martin
The Sanctimonious Kid The Sanctimonious Kid   See fewer
Jobie James
Businessman Businessman   See fewer
Jamie Loy
Audience Member Audience Member   See fewer
Gabrielle Lane
Rowdy Prostitute Rowdy Prostitute   See fewer
Tony Doupe
Logger Logger   See fewer
Anthony A. Kung
Chinese Man Chinese Man   See fewer
JulieAnna Rohde
Audience Member Audience Member   See fewer
Henry Mark
Chew Chee Chew Chee   See fewer
Morgen Johnson
Repo man Repo man   See fewer
Skyler Verity
Young Jack Young Jack   See fewer
Jim Hamerlinck
Goldtooth Goldtooth   See fewer
Chris LeBlanc
Corbett Corbett   See fewer
Melissa Pang
Toothless Chinese Woman Toothless Chinese Woman   See fewer
Ryan Sanders
Constable Constable   See fewer
Robert Zorn
Chicken Bum Chicken Bum   See fewer
Brandon E. Jackson
Prison Guard Prison Guard   See fewer
Billy Dyke
Police Officer Police Officer   See fewer
Greg Williams
Upperclass Gentleman Upperclass Gentleman   See fewer
Laura Elizabeth Dawes
Audience Member Audience Member   See fewer
Ronnie Felts
Audience Member Audience Member   See fewer
Jay G. Hill
Angry logger Angry logger   See fewer
Carson Leasure
Angry Logger Angry Logger   See fewer
Raphael Carlo
Tripped Bum Tripped Bum   See fewer
Josh Chapman
Audience member Audience member   See fewer
Diana Dee Pascual
Prostitute Prostitute   See fewer
Lindsay Crisp
Society Lady Society Lady   See fewer
Matthew Shell
Dead Guy Dead Guy   See fewer
William Warren Ward
Frying Pan Bum (as Will Ward) Frying Pan Bum (as Will Ward)   See fewer
Justin Pappan
Boxcar Hobo Boxcar Hobo   See fewer
Chase Humphrey
Audience Member Audience Member   See fewer
Landon Morgan
Businessman Businessman   See fewer
Gavin McLeroy
Wolfish Boy Wolfish Boy   See fewer
Gene Kelly
Actor Actor   See fewer
Russell W. Reed
Shirtless heavyset man Shirtless heavyset man   See fewer
Martin Park
Homeowner Homeowner   See fewer
Jennifer Angelucci-Medina
Actress (uncredited) Actress (uncredited)   See fewer
Will Bean
Opium Den Gentlemen (uncredited) Opium Den Gentlemen (uncredited)   See fewer
Dwayne Bell
Actor (uncredited) Actor (uncredited)   See fewer
Colin Joseph Cole
Actor (uncredited) Actor (uncredited)   See fewer
Eva Jane
Actress (uncredited) Actress (uncredited)   See fewer
David Kirwan
Actor (uncredited) Actor (uncredited)   See fewer
Michele B. McGraw
Audience Member (uncredited) Audience Member (uncredited)   See fewer
Christophe Murdock
Passerby (uncredited) Passerby (uncredited)   See fewer
Leland Prater
Passerby (uncredited) Passerby (uncredited)   See fewer
Troy Wilson
Passerby (uncredited) Passerby (uncredited)   See fewer
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