A failed New York playwright stages a suicide in an attempt to win back her ex, only to wind up in the custody of her gambling-addict mother.
| Actor | Role |
|---|---|
 Kristen WiigImogene | Imogene |
 Annette BeningZelda | Zelda |
 Matt DillonGeorge | George |
 Darren CrissLee | Lee |
 Christopher FitzgeraldRalph | Ralph |
 June Diane RaphaelDara | Dara |
 Natasha LyonneAllyson | Allyson |
 Bob BalabanMaxwell | Maxwell |
 Sydney LucasLittle Imogene | Little Imogene |
 Jimmy PalumboDoorman Joe | Doorman Joe |
 Michelle MorganGeorgina | Georgina |
 Mickey SumnerHannah | Hannah |
| EElizabeth InghramSloane | Sloane |
 Brian PetsosPeter Van Woodsen | Peter Van Woodsen |
 Murray BartlettJames Whitney | James Whitney |
 Melissa NaviaAssistant | Assistant |
 Michelle HurdLibby | Libby |
| JJennifer FoxHotel Clerk | Hotel Clerk |
 Cynthia NixonCynthia Nixon | Cynthia Nixon |
 Reed BirneyDr. Chalmers | Dr. Chalmers |
| MManny SiverioGino | Gino |
| NNnamdi NwosaBruce | Bruce |
| CClare GalterioAnnouncer | Announcer |
 Akira TakayamaCasino Gambler | Casino Gambler |
 Helmar Augustus CooperDelancey Security Guard | Delancey Security Guard |
 Tandy CronynHermione | Hermione |
| NNicole PatrickMonica | Monica |
| BBronsonHermit Crab | Hermit Crab |
 Nate CorddryLarry Feinstein | Larry Feinstein |
 Mike KellerNJ Cop / T-Rex Rinaldi | NJ Cop / T-Rex Rinaldi |