Woody Allen David Dobel Director, Actor, Writer Jason Biggs Jerry Falk Actor Christina Ricci Amanda Actor Danny DeVito Harvey Actor Stockard Channing Paula Actor Jimmy Fallon Bob Actor Erica Leerhsen Connie Actor William Hill Psychiatrist Actor David Conrad Dr. Reed Actor Adrian Grenier Ray Polito Actor Diana Krall Self Letty Aronson Producer Helen Robin Co-Producer Stephen Tenenbaum Executive Producer Jack Rollins Co-Executive Producer Charles H. Joffe Co-Executive Producer Darius Khondji Cinematographer Alisa Lepselter Film Editing Santo Loquasto Production Design Tom Warren Art Director Regina Graves Set Decoration Laura Jean Shannon Costume Design Juliet Taylor Casting Laura Rosenthal Casting