Special Guest Stars Jeannie Berlin as Ruth Heidelbaum Guest Stars Jonno Davies as Tobias Henry Hunter Hall as Cheeks Johnson Ebony Obsidian as Carol Lockhart Annie Hägg as Young Ruth Zack Schor as Young Meyer James Le Gros as Chief Harry Grimsby Caleb Emery as Arthur "Bootyhole" McGuigan Kenneth Tigar as Heinz Richter Jason Kravits as Rabbi Grossman Victor Williams as Detective Kennedy Groton Tramell Tillman as Detective Sommers Izabella Miko as Helen Hirsch Leigh Ann Larkin as Lottie Simpson Gordon Winarick as Dennis Duncan Veronika Nowag-Jones as Gretel Fischer Co Starring Cassidy Layton as Chava Apfelbaum James Rutledge as Edward / Butler Danny Doherty as Meyer's Driver Judy Rosenblatt as Mrs. Schlosstein Brandon Engman as Teen Clerk David Sitler as King Lear Man Manny Galan as Hell Devils Leader Joshua Alscher as Chess Board Prisoner #11 Allison Wick as Chess Board Prisoner #8 Audrey Bennett as Trinity Simpson Jaxon Bartok as Sawyer Simpson Zack Segel as Surly Waiter Lesley Noyes as Chess Board Prisoner #3 Sophia Gonzalez as Little Girl in Toy Shop Kyle Leibovitch as Chess Board Prisoner #14 Sara Tepper as Chess Board Prisoner #13 Alison Maddren as Chess Board Prisoner #12 Riley Galt as Chess Board Prisoner #9 Richard Ruskin as Chess Board Prisoner #6 Paul Grossman as Chess Board Prisoner #4 Ryan Welsh as Chess Board Prisoner #15 Ari Tomais as Chess Board Bishop Markus McClain as Chess Board Prisoner #2 Inna Yesilevskaya as Wailing Woman Mick Diflo as Skeezy Man Anna Podolak as Angry Woman John Basedow as News Anchor #1 Brandon Elia as Rookie Cop Holly Grum as Chess Board Knight Stephen Pilkington as Carl Hirsch T. Ryder Smith as Ulysses F. O'Harrison Logan Crawford as News Anchor #2 Tracie Higgins as Judy Brown Karen Chmielnicki as Chess Board Prisoner #5 Bill Timoney as Congresman Marshall Vince Eisenson as Chess Board Prisoner #1 Musto Pelinkovicci as Rebbe Apfelbaum Max MacKenzie as Markus Roth Frank Bal as Terry Chloe Ava Bryan as Girl in Laundromat Jack Sochet as Chess Board Prisoner #7 Julianna Pitt as Chess Board Prisoner #10 Andrew Rogers as Joe Brown Marc Schottner as Nazi Administrator Jeremy Lanuti as Biff Jr. Ava Eisenson as Lost Woman Stephen D'Ambrose as Nasa Suit #1 Calvin Knie as Young Heinz Richter