Guest Stars Phil Morris as Jackie Chiles Brenda Strong as Sue Ellen Judy Kerr as Woman Debra Jo Rupp as Katie Bob Odenkirk as Ben Kyle Gass as Smoker David Letterman as Himself Fern Fitzgerald as Ms. Wilkie Alex Trebek as Himself Derek Jeter as Himself Meagen Fay as Mrs. Burns Lawrence Mandley as Larry the Cook Bernie Williams as Himself Tamara Bick as Louise Noelle Balfour as Waitress Uncredited Ruth Cohen as Ruthie Cohen Randy Carter as Rick