Sam Rockwell character Chuck Barris
Drew Barrymore character Penny
George Clooney character CIA Agent Jim Byrd
Julia Roberts character Patricia Watson
Rutger Hauer character Keeler
Jerry Weintraub character Larry Goldberg
Maggie Gyllenhaal character Debbie
Michael Ensign character Simon Oliver
Michael Cera character Chuck
Jennifer Hall character Georgia
Matt Damon character Matt, 2nd Bachelor
Brad Pitt character Brad, 1st Bachelor
David Julian Hirsh character Freddie Cannon
Rachelle Lefevre character Tuvia, Age 25
Sean Tucker character Barfly
Ilona Elkin character Georgia's Girlfriend
Andy Quesnel character Gong Show Model
Krista Allen character Pretty Woman
Jaye P. Morgan character Herself
Dick Clark character Himself
Michelle Sweeney character J. Sweeney
Anna Silk character Headset Woman
Richard Kind character Casting Executive Man
Steve Adams character Dating Game Director
Dino Tosques character L.A. Bartender
Linda Tomassone character Monica (uncredited)
Robert John Burke character Instructor Jenks
