Multiplayer Leagues Leaderboard Updates

Loading movie…

You Can't Win (2026) — Cast & Connections | FilmLink

Turn movie knowledge into a game

Explore You Can't Win's cast and crew, then connect two films in FilmLink's free daily movie game.

Play today's movie game Learn to play

Backdrop

You Can't Win

You Can't Win2026

★4.9139 minWestern

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.

Director

Writer

Charles Mudede Robinson Devor Barry Gifford Michael Pitt

Score

Paul Matthew Moore

Stars

Michael Pitt Ivan Martin Will Patton

Cast48

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
J
Jenni Bradstreet
as Chinese Sleeper
J
Jim Chow
as Chinese Sleeper
T
Tony Lao
as Chinese Sleeper
D
David Leong
as Chinese Sleeper
H
Hutch Stellick
as Boy Jack
Ted Rooney
as Jack's Father
Skyler Verity
as Young Jack
Brandon E. Jackson
as Prison Guard
C
Charles Baker
as Fremont Older
Rusty Tennant
as Depot Policeman
Chris LeBlanc
as Corbett
R
Robert Zorn
as Jungle Bum
W
William Warren Ward
as Jungle Bum
E
Earl Alexander
as Jungle Bum
R
Ron Lampman
as Jungle Bum
R
Rob Finney
as Jungle Bum
A
Art Hickman
as Jungle Bum / Pharmacist
K
Ken Clark
as Jungle Bum
T
Tim Henderson
as Jungle Bum
Robert Blanche
as Cy
H
Henry Mark
as Chew Chee
A
Alex Terzieff
as Work Crew Boss
T
Todd Lagestee
as Work Crew Guard
Louisa Krause
as Irish Annie
R
Ron Otis
as Hotel Detective
John Paulsen
as Junkie Husband
Kathy Hsieh
as Junkie Wife
J
Jim Hamerlinck
as Goldtooth
J
James Lapan
as Station Agent
S
Stella Diaz
as Station Agent's Wife
M
Mark Fullerton
as Canadian Constable
S
Scott
as Murphey
Anatol Yusef
as Dirty Dick
Anthony A. Kung
as Opium Den Pickpocket
A
Alexis Scarff
as Ghost Mother
W
Wesley Scarff
as Baby Jack
K
Kori Ennis
as Salon Patron
D
David Beck
as Salon Patron

This product uses the TMDB API but is not endorsed or certified by TMDB.

More like this

True Grit

The Stalking Moon

The Stalking Moon

Hud

Ramrod

Hombre

Barbarosa

Bandolero!

Rancho Notorious

Rancho Notorious

3:10 to Yuma

The Way West

Monte Walsh

Barquero

The Bravados

Day of the Outlaw

Day of the Outlaw

Man Without a Star

Man Without a Star

The Last Hard Men

The Last Hard Men

Broke

The Sisters Brothers

The Sisters Brothers

Guns for San Sebastian

Guns for San Sebastian

The Warrior's Way

The Warrior's Way