Guest Stars Mo Collins as Joan Callamezzo Billy Eichner as Craig Middlebrooks Andy Forrest as Kyle Dan Castellaneta as Derry Murbles Nick Toth as Producer Aly Mawji as Ragiv John Hodgman as August Clementine Debra Mooney as Rosie Demarco Peter Bonerz as Doug Demarco Josh Breeding as Terk Rastersnyke