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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 |
After being ejected from his job for one too many vulgar and inappropriate comments, Leon unsuccessfully seeks employment from every radio station in Chicago. He receives a mysterious letter from his true love asking him to return to her -- he just has to figure out who it is!
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