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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 |
The career and personal life of writer Lee are at a standstill, so he divorces his bashful wife, Robin, and dives into a new job as an entertainment journalist. His assignments take him to the swankiest corners of Manhattan, but as he jumps from one lavish party to another and engages in numerous empty romances, he starts to doubt the worth of his work. Meanwhile, top TV producer Tony falls for Robin and introduces her to the world of celebrity.
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