Special Guest Stars Jon Hamm as Richard Wayne Gary Wayne Guest Stars David Cross as Russ Snyder Josh Charles as Duke Snyder Fred Armisen as Robert Durst Harris Yulin as Orson Snyder Lisa Kudrow as Lori-Anne Schmidt Co Starring Asa Somers as Drew Mark Doherty as Flash Todd Susman as Ilan Carlos Navarro as Coaster Head Joe Pat Kiernan as Himself Lou Carbonneau as Winfred Ian Roberts as Captain Mooney Joy Kigin as Boy's Mom Rob Gorden as Jerk Parent Adam Hose as Boy's Dad Mike Benitez as Bus Driver Violet Krumbein as Lisa Olli Haaskivi as Shane Robert Buchanan as Fear Factor Host Avery Burns as Toddler