Special Guest Stars Kyle MacLachlan as Dickie Pope Catherine Keener as Herself Guest Stars Nancy Robertson as Billie Alvina August as June Washington-Chen Shannon DeVido as Emma Haig Sutherland as Finny Arthur Keng as Teddy Washington-Chen Oscar Nuñez as Dean Rose Daniel Doheny as Russell Jackson Kelly as Bartow Williams-Stevens Anne Gee Byrd as Laurel Devereaux Jennifer Spence as Ashley Tom Bower as Henry Devereaux Sr. Chris Gethard as Jeffrey Q. Epstein Co Starring Ellen MacNevin as Rachel Dolores Drake as Jill Bernie Yao as Dennis Hayley Sales as Missy Veronica Jarvis as Mina Brian Calvert as Professor #4 Shelley Janze as Professor #2 Brent Clark as Professor #3 Vincent Cheng as Professor #1