George Clooney

Jim Byrd

Steven Soderbergh

Executive Producer

Drew Barrymore

Penny

Maggie Gyllenhaal

Debbie

Sam Rockwell

Chuck Barris

Harvey Weinstein

Executive Producer

Bob Weinstein

Executive Producer

Michael Cera

Chuck (8 & 11 years)

James Urbaniak

Rod Flexner

Dick Clark

Self

Emilio Rivera

Benitez

Julia Roberts

Patricia Watson

Michael Ensign

Simon Oliver

Rutger Hauer

Keeler

Daniel Zacapa

Renda

Carlos Carrasco

Brazioni

Jonathan Gordon

Executive Producer

Krista Allen

Pretty Woman

Kristen Wilson

Loretta

Rand Ravich

Executive Producer

Michelle Sweeney

Housekeeper

Robert John Burke

Instructor Jenks

Jennifer Hall

Georgia

J. Todd Anderson

Stud Bachelor

Aimee Rose Ambroziak

Chuck's Date #1

Isabelle Blais

Chuck's Date #2

Melissa Carter

Chuck's Date #3

Ilona Elkin

Georgia's Girlfriend

Sean Tucker

Barfly

Stephen Evans

Executive Producer