Special Guest Stars Gary Cole as Kurt McVeigh Michael Sheen as Roland Blum Guest Stars Brenda Braxton as Madeline Gilford Tamberla Perry as Judge Charlotte Hazlewood Kate Shindle as Rachelle Max Rashad Edwards as Jim / Mail Room Clerk Christina Jackson as Leah Davis Keith Randolph Smith as John Wilson Rachel Wenitsky as Lili Brenner Daniel Davis as Professor Harrison Chris Sullivan as Judge Dash Toosi John Earl Jelks as Perry Cardwell Elizabeth Ward Land as Maggie Co Starring Jordan Boatman as Associate Lucy Nathan Stark as Process Server Josh Bonzie as Associate Micah Anastacia McCleskey as Associate Opal Susannah Hoffman as ASMR Video Woman David Aron Damane as Baliff Will Vought as Warm-Up Comic Michael Sean McGuinness as Terrence Parnell Bill Evans as Weatherman Bill