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Sam Rockwell

Chuck Barris

Drew Barrymore

Penny

George Clooney

CIA Agent Jim Byrd

Julia Roberts

Patricia Watson

Rutger Hauer

Keeler

Brad Pitt

Brad, 1st Bachelor

Matt Damon

Matt, 2nd Bachelor

Jerry Weintraub

Larry Goldberg

Maggie Gyllenhaal

Debbie

Michael Cera

Chuck

Michael Ensign

Simon Oliver

Jennifer Hall

Georgia

David Julian Hirsh

Freddie Cannon

Rachelle Lefevre

Tuvia, Age 25

Sean Tucker

Barfly

Ilona Elkin

Georgia's Girlfriend

Andy Quesnel

Gong Show Model

Krista Allen

Pretty Woman

Jaye P. Morgan

Herself

Dick Clark

Himself

Michelle Sweeney

J. Sweeney

Anna Silk

Headset Woman

Richard Kind

Casting Executive Man

Steve Adams

Dating Game Director

Dino Tosques

L.A. Bartender

Linda Tomassone

Monica (uncredited)

Charlie Kaufman

Writing

Bob Weinstein

Production

Harvey Weinstein

Production

George Clooney

Directing

Steven Soderbergh

Production

Renée April

Costume & Make-Up

James D. Bissell

Art

Newton Thomas Sigel

Camera

Rand Ravich

Production

Alex Wurman

Sound

Donald Dowd

Editing

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