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 Debra Mooney as Rosie Demarco Peter Bonerz as Doug Demarco John Hodgman as August Clementine Josh Breeding as Terk Rastersnyke