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.

Drama

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)

Charles Baker

(Fremont Older)

Rusty Tennant

(Depot Policeman)

Chris LeBlanc

(Corbett)

Robert Zorn

(Jungle Bum)

William Warren Ward

(Jungle Bum)

Earl Alexander

(Jungle Bum)

Ron Lampman

(Jungle Bum)

Rob Finney

(Jungle Bum)

Art Hickman

(Jungle Bum / Pharmacist)

Ken Clark

(Jungle Bum)

Tim Henderson

(Jungle Bum)

Robert Blanche

(Cy)

Henry Mark

(Chew Chee)

Alex Terzieff

(Work Crew Boss)

Todd Lagestee

(Work Crew Guard)

Louisa Krause

(Irish Annie)

Ron Otis

(Hotel Detective)

John Paulsen

(Junkie Husband)

Kathy Hsieh

(Junkie Wife)

Jim Hamerlinck

(Goldtooth)

James Lapan

(Station Agent)

Stella Diaz

(Station Agent's Wife)

Mark Fullerton

(Canadian Constable)

Scott

(Murphey)

Anatol Yusef

(Dirty Dick)

Anthony A. Kung

(Opium Den Pickpocket)

Alexis Scarff

(Ghost Mother)

Wesley Scarff

(Baby Jack)

Kori Ennis

(Salon Patron)

David Beck

(Salon Patron)