Special Guest Stars Kyle MacLachlan as Dickie Pope Catherine Keener as Herself Guest Stars Alvina August as June Washington-Chen Nancy Robertson as Billie Haig Sutherland as Finny Arthur Keng as Teddy Washington-Chen Shannon DeVido as Emma Oscar Nuñez as Dean Rose Daniel Doheny as Russell Anne Gee Byrd as Laurel Devereaux Jackson Kelly as Bartow Williams-Stevens 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 Hayley Sales as Missy Bernie Yao as Dennis Veronica Jarvis as Mina Brian Calvert as Professor #4 Shelley Janze as Professor #2 Brent Clark as Professor #3 Vincent Cheng as Professor #1