Special Guest Stars Gil Bellows as Billy Thomas Taye Diggs as Jackson Duper James Naughton as George McBeal Jill Clayburgh as Jeannie McBeal Guest Stars Albert Hall as Judge Seymore Walsh Regina Hall as Corretta Lipp Alexandra Holden as Jane Wilco Leslie Jordan as Dr. Benjamin Harris Josh Groban as Malcolm Wyatt Shirley Prestia as Saleswoman Co Starring Renée Elise Goldsberry as Singer Vatrena King as Singer Sy Smith as Singer Talia-Lynn Prairie as Young Ally Ryan Hansen as Student MC Verda Bridges as Drill Sergeant Jessica Townsend as Wendy Harry Wayne Casey as Himself Paityn James as Andrea Mason Uncredited Brandy Schaefer as Dancer Tara Nicole Hughes as Mannequin Bride