Sam Rockwell

Chuck Barris

Drew Barrymore

Penny

George Clooney

Jim Byrd

Julia Roberts

Patricia Watson

Rutger Hauer

Keeler

Maggie Gyllenhaal

Debbie

Robert John Burke

Instructor Jenks

Jennifer Hall

Georgia

Kristen Wilson

Loretta

Carlos Carrasco

Brazioni

Emilio Rivera

Benitez

Daniel Zacapa

Renda

Krista Allen

Pretty Woman

Michael Ensign

Simon Oliver

James Urbaniak

Rod Flexner

Dick Clark

Self

Michelle Sweeney

Housekeeper

Michael Cera

Chuck (8 & 11 years)

Isabelle Blais

Chuck's Date #2

Melissa Carter

Chuck's Date #3

Ilona Elkin

Georgia's Girlfriend

Sean Tucker

Barfly

Jaye P. Morgan

Self

David Julian Hirsh

Freddie Cannon

Jerry Weintraub

Larry Goldberg

Frank Fontaine

ABC Executive

Rachelle Lefevre

Tuvia (25 years)

Barbara Bacci

Woman in Veil

Janet Lane

Blonde Bachelorette

Shaun Balbar

Beanpole Bachelor

Michael Filipowich

Handsome Bachelor

Samantha Kaine

Black Bachelorette

Christian Paul

Black Bachelor

Steve Adams

Dating Game Director

Maria Bertrand

Stud Bachelorette

Brad Pitt

Bachelor Brad

Matt Damon

Bachelor Matt

Murray Langston

Actual Unknown Comic

Claudia Besso

Chuck's Mother

Isabelle Juneau

Amana Girl

Richard Kind

Casting Executive Man

Shu Lan Tuan

Asian Folksinger #2

Bridget Powers

Little Person

Dino Tosques

L.A. Bartender

Joe Cobden

Unknown Comic

Tommy Hinkley

Hambone Man

Chuck Barris

Actual Barris