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| Hank Azaria | David |
| Kenneth Branagh | Lee Simon |
| Judy Davis | Robin Simon |
| Leonardo DiCaprio | Brandon Darrow |
| Melanie Griffith | Nicole Oliver |
| Famke Janssen | Bonnie |
| Michael Lerner | Dr. Lupus |
| Joe Mantegna | Tony Gardella |
| Bebe Neuwirth | Nina - the Hooker |
| Winona Ryder | Nola |
| Charlize Theron | Supermodel |
| Greg Mottola | Director |
| Dylan Baker | Priest at Catholic Retreat |
| Isaac Mizrahi | Bruce Bishop |
| Kate Burton | Robin's Friend Cheryl |
| Andre Gregory | John Papadakis |
| Patti D'Arbanville | Iris |
| Gretchen Mol | Vicky |
| Mary Jo Buttafuoco | Herself |
| Joey Buttafuoco | Himself |
| Allison Janney | Evelyn Isaacs |
| Donald Trump | Himself |
| Aida Turturro | Olga - Psychic |
| Jeffrey Wright | Greg - Off-Off Broadway Director |
In the wake of their split, a neurotic writer and his insecure wife seek new relationships and direction.
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