Sam Rockwell as Chuck Barris

Drew Barrymore as Penny

George Clooney as Jim Byrd

Julia Roberts as Patricia Watson

Rutger Hauer as Keeler

Maggie Gyllenhaal as Debbie

Robert John Burke as Instructor Jenks

Jennifer Hall as Georgia

Kristen Wilson as Loretta

J. Todd Anderson as Stud Bachelor

Carlos Carrasco as Brazioni

Emilio Rivera as Benitez

Daniel Zacapa as Renda

Krista Allen as Pretty Woman

Michael Ensign as Simon Oliver

James Urbaniak as Rod Flexner

Dick Clark as Self

Michelle Sweeney as Housekeeper

Michael Cera as Chuck (8 & 11 years)

Aimee Rose Ambroziak as Chuck's Date #1

Isabelle Blais as Chuck's Date #2

Melissa Carter as Chuck's Date #3

Ilona Elkin as Georgia's Girlfriend

Sean Tucker as Barfly

Jaye P. Morgan as Self

David Julian Hirsh as Freddie Cannon

Jerry Weintraub as Larry Goldberg

Frank Fontaine as ABC Executive

Rachelle Lefevre as Tuvia (25 years)

Gene Patton as Gene Gene Patton

Barbara Bacci as Woman in Veil

Janet Lane as Blonde Bachelorette

Shaun Balbar as Beanpole Bachelor

Jeff Lefebvre as Frizzy Hair Bachelor

Michael Filipowich as Handsome Bachelor

Samantha Kaine as Black Bachelorette

Christian Paul as Black Bachelor

Jim Lange as Self

Steve Adams as Dating Game Director

Maria Bertrand as Stud Bachelorette

Brad Pitt as Bachelor Brad

Matt Damon as Bachelor Matt

Murray Langston as Actual Unknown Comic

Marlida Ferreira as Woman in Pub

Jérôme Tiberghien as Englishman

Martin Kevan as Chuck's Father

Claudia Besso as Chuck's Mother

Isabelle Juneau as Amana Girl

Nathalie Morin as Bachelorette Winner

Tony Zanca as Bachelor Winner

Sergei Priselkov as Shaving Man

Norman Roy as Colbert

Marlene Fisher as Casting Executive Woman

Richard Kind as Casting Executive Man

Suyun Kim as Asian Folksinger #1

Shu Lan Tuan as Asian Folksinger #2

Andre Minicozzi as Gong Show Band

Richard Beaudet as Gong Show Band

Ron Di Lauro as Gong Show Band

Peter N. Wilson as Gong Show Band

Bruce Pepper as Gong Show Band

Francois St-Pierre as Gong Show Band

Bridget Powers as Little Person

George Randolph as Gene Gene

Pascale Devigne as Critic

Carlo Berardinucci as Waiter

Tanya Anthony as Prostitute

Andy Quesnel as Gong Show Model

Keshav Patel as Elvis Singer

Leslie Cottle as L.A. Bar Woman

Dino Tosques as L.A. Bartender

Joe Cobden as Unknown Comic

Ethan Thomas C. Dempster as Chuck (3 years)

Tommy Hinkley as Hambone Man

Bill Corday as Justice of the Peace

Chuck Barris as Actual Barris

Chelsea Ceci as Tuvia, Age 8