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