Guest Stars Kevin Christy as Lester Linden Betty Gilpin as Nancy Leveau Jeremy Strong as Art Dreesen Jack Laufer as Herb Spleeb David Walton as Bram Keller John Gleeson Connolly as Hugh Hefner Judy Greer as Alice Logan Ashley Zukerman as Gary Bucksey Amanda Quaid as Fran Bucksey Andre Royo as Sammy Davis Jr. Bryce Johnson as Lee Dirks Gabriel Tigerman as Scotty Co Starring Andrea Gwynnel Morgan as Waitress Nicole Cummins as Doe Eyes Rachelle Dimaria as Dawn Jackson Nathan Mohebbi as Todd Holstein Jaret Sacrey as Fred Cox