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| Tim Meadows | Leon Phelps |
| Karyn Parsons | Julie |
| Billy Dee Williams | Lester |
| Will Ferrell | Lance |
| Lee Evans | Barney |
| Tiffani Thiessen | Honey DeLune |
| John Witherspoon | Scrap Iron |
| Jill Talley | Candy |
| Sofia Milos | Cheryl |
| Eugene Levy | Bucky Kent |
| Tamala Jones | Theresa |
| Julianne Moore | Audrey |
| Sean Thibodeau | Hugh Hefner |
A late-night radio host and self-described Casanova searches for a lost love when he receives an unsigned letter boasting of her wealth.
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