Guest Stars Albert Hall as Judge Seymore Walsh Lisa Edelstein as Cindy McCauliff Jami Gertz as Kimmy Bishop William Russ as Michael Bassett Michael Vartan as Jonathan Bassett Louie Anderson as Therapist Don McManus as Greg Harrod Co Starring Renée Elise Goldsberry as Singer Vatrena King as Singer Sy Smith as Singer Terry Walters as Andrea Bassett Joe Ochman as Patron #1 Lisa Brounstein as Beatrice Karen Furno as Clerk Gail Bearden as Patron #2 Jeffrey Osborne as Himself