Guest Stars Jon Glaser as Councilman Jeremy Jamm Billy Eichner as Craig Middlebrooks Andy Forrest as Kyle Kevin Symons as Councilman Bill Dexhart Richard Lee Burch as Herman Lerpiss Cooper Thornton as Dr. Harris Henry Winkler as Dr. Saperstein Rylan Lee as Ivy Lewis Sadie Salazar as Zoey Lewis Keegan-Michael Key as Joe Mike Scully as Pearl Caroline Hall as Barbara Brabrababar