Tod Harrison Williams Director, Screenwriter Seann William Scott Jeff Actor Gretchen Mol Lynn Actor Jeff Garlin Lenny Actor Denis O'Hare Mike Actor Kevin Conway Bert Actor Charlie Tahan Little Jeff Actor Paul Scheer Junior Actor Stephen Adly Guirgis Captain Al Actor Jayce Bartok Brian From Boarding School Actor Erica Fae Receptionist Actor Ian Buchanan Terry Actor Elie Samaha Producer Daniel Sadek Producer Anne Carey Producer Rob Delp Producer Al Hayes Executive Producer Michael Simmonds Cinematographer Affonso Gonçalves Film Editing Marcelo Zarvos Original Music David Doernberg Production Design Sara Parks Set Decoration Eric Daman Costume Design Nicole Abellera Casting Jeanne McCarthy Casting