Crazy on the Outside

Tim Allen

— Tommy

Sigourney Weaver

— Viki

Ray Liotta

— Gray

J.K. Simmons

— Ed

Julie Bowen

— Christy

Kelsey Grammer

— Frank

Jeanne Tripplehorn

— Angela

Helen Slayton-Hughes

— Grandma

Kenton Duty

— Ethan Papadopolous

Daniel Booko

— Cooper Luboja

Karle Warren

— Alex Luboja

Robert Baker

— Lance

Casey Sander

— Prison Guard

Jon Gries

— Edgar

Malcolm Goodwin

— Rick

John Hayden

— Judge Pierce

Meeghan Holaway

— Tina

Jean St. James

— Mrs. Pierce

Rocky La Porte

— Rocky

Mariano Mendoza

— Prisoner #1

Scarlett Chorvat

— Cindy

Hector Atreyu Ruiz

— Prisoner #2

Annie McKnight

— Drive-Thru Pirate

Evelyn Iocolano

— Denise/Hygienist

Rosa Nellie Ruiz

— Maid

Paul Tranghese

— Holding Cell Cop

Maggie Palomo

— Counter Person

Tahmus Rounds

— Pee Cup Guy

Jeff Kueppers

— Steve/Walking Man

Darla Delgado

— Gray's Girlfriend