Special Guest Stars Taye Diggs as Jackson Duper Sting as Himself Guest Stars Albert Hall as Judge Seymore Walsh Regina Hall as Corretta Lipp John Michael Higgins as Attorney Steven Milter Christopher Neiman as Attorney Barry Mathers Cheri Oteri as Melissa Paul Reubens as Louis Cindy Margolis as Herself Scott Klace as Dr. Hobey Jim Bailey as Harold Dale Co Starring Renée Elise Goldsberry as Singer Sy Smith as Singer Cynthia Calhoun as Singer Uncredited Karen-Eileen Gordon voices Alarm Clock Myron J. Hyman as Guitar Player