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| Caroline Aaron | Doris |
| Woody Allen | Harry Block |
| Kirstie Alley | Joan |
| Bob Balaban | Richard |
| Richard Benjamin | Ken |
| Eric Bogosian | Burt |
| Billy Crystal | Larry / The Devil (Harry's Character) |
| Judy Davis | Lucy |
| Hazelle Goodman | Cookie |
| Mariel Hemingway | Beth Kramer |
| Amy Irving | Jane |
| Julie Kavner | Grace / Harry's Character |
| Eric Lloyd | Hilly |
| Julia Louis-Dreyfus | Leslie |
| Tobey Maguire | Harvey Stern |
| Demi Moore | Helen / Harry's Character |
| Elisabeth Shue | Fay |
| Stanley Tucci | Paul Epstein / Harry's Character |
| Robin Williams | Mel / Harry's Character |
| Annette Arnold | Rosalee |
| Philip Bosco | Prof. Clark |
| Stephanie Roth | |
| Gene Saks | Harry's Father |
An immature middle-aged writer with lifelong women problems seeks someone to accompany him to an awards ceremony.
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