Paul Dinello Mr. Geoffrey Jellineck Director, Actor, Writer Amy Sedaris Jerri Blank Actor, Writer Deborah Rush Sara Blank Actor Carlo Alban Megawatti Sukharnabhoutri Actor Maria Thayer Tammi Littlenut Actor Stephen Colbert Mr. Charles "Chuck" Noblet Actor, Writer Chris Pratt Brason Actor Elisabeth Harnois Monica Actor Joseph Cross Derrick Blank Actor Greg Hollimon Principal Blackman Actor Dan Hedaya Guy Blank Actor Matthew Broderick Dr. Roger Beekman Actor David Pasquesi Stew Actor Alexis Dziena Melissa Actor Ian Holm Dr. Putney Actor Sarah Jessica Parker Peggy Callas Actor Allison Janney Alice Actor Philip Seymour Hoffman Henry Actor Kristen Johnston Coach Muffy Divers Actor Justin Theroux Mr. Carlo Honklin Actor Lorena David Producer Mark Roberts Producer David Letterman Executive Producer Oliver Bokelberg Cinematographer Teresa Mastropiero Production Design Mylene Santos Art Director Siobain Flaherty Set Decoration Michael R. Miller Film Editing Marcelo Zar Original Music Victoria Farrell Costume Design