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Dick Clark - Self, Sam Rockwell - Chuck Barris, Michelle Sweeney - J. Sweeney, Drew Barrymore - Penny, Chelsea Ceci - Tuvia, Age 8 Michael Cera - Chuck Age 8 and 11 (as Michael Céra) , Aimee Rose Ambroziak - Chuck's Date #1 Isabelle Blais - Chuck's Date #2 Melissa Carter - Chuck's Date #3 Jennifer Hall - Georgia, Ilona Elkin - Georgia's Girlfriend, Sean Tucker - Barfly, Jaye P. Morgan - Self, Maggie Gyllenhaal - Debbie, David Julian Hirsh - Freddie Cannon (as David Hirsh)