Special Guest Stars Beau Bridges as Roy Wheeler Guest Stars Paul Williams as James "JT" Reginald III Griffin Dunne as Gene Bennett Illeana Douglas as Rita Marisa Echeverria as Violet Webster Matthew Weiner as Matthew DeLanna Studi as Delores Co Starring Peter Asle Holden as Warren Hebb Chrystee Pharris as Gloria Greg Bryan as Hugo Marshall Cook as Gerry Kernan Hope Banks as Waitress Anna Carini as Dr. Mindy Levine Paul Toweh as Vinnie Brandon Young as Van Driver Ravinderpaul S. Tut as Employee