Woody Allen Harry Block Director, Actor Caroline Aaron Doris Actor Kirstie Alley Joan Actor Bob Balaban Richard Actor Richard Benjamin Ken Actor Eric Bogosian Burt Actor Billy Crystal Larry , The Devil (Harry's Character) Actor Judy Davis Lucy Actor Hazelle Goodman Cookie Actor Mariel Hemingway Beth Kramer Actor Amy Irving Jane Actor Julie Kavner Grace , Harry's Character Actor Eric Lloyd Hilly Actor Julia Louis-Dreyfus Leslie Actor Tobey Maguire Harvey Stern Actor Demi Moore Helen , Harry's Character Actor Elisabeth Shue Fay Actor Stanley Tucci Paul Epstein , Harry's Character Actor Robin Williams Mel , Harry's Character Actor Annette Arnold Rosalee Actor Philip Bosco Prof. Clark Actor Stephanie Roth Haberle Janet Actor Gene Saks Harry's Father Actor Dan Morando Devil Actor Ray Garvey Policeman on Campus Actor Linda Perri Policewoman on Campus Actor Tony Sirico Policeman at Jail Actor Ray Aranha Professor Aranha Actor Paul Giamatti Professor Abbott Actor Marvin Chatinover Professor Cole Actor Daniel Wolf Professor Wolf Actor Gene Troobnick Professor Wiggins Actor Viola Harris Elsie Actor Letty Aronson Co-Executive Producer J.E. Beaucaire Executive Producer Richard Brick Co-Producer Jean Doumanian Producer Charles H. Joffe Co-Executive Producer Jack Rollins Co-Executive Producer Carlo Di Palma Cinematographer Susan E. Morse Film Editing Juliet Taylor Casting Santo Loquasto Production Design Tom Warren Art Director Susan Kaufman Set Decoration Elaine O'Donnell Set Decoration Suzy Benzinger Costume Design