Special Guest Stars Gary Cole as Kurt McVeigh Guest Stars Tamberla Perry as Judge Charlotte Hazlewood Chasten Harmon as Bianca Skye Hugh Dancy as Caleb Garlin Carson Elrod as Josiah Nile Fisher Stevens as Gabe Kovac Lisa O'Hare as STR Laurie Gatekeeper Nikki M. James as Monica Timmons Erik King as Julius Cain Character / Jonah LaChanze as Julius's Wife Raúl Esparza as Bryan Kneef Jon Michael Hill as Jumaane Jenkins / Alan North Kirsten Scott as Diane Lockhart Character / Dana Ben Graney as Avi Keilly McQuail as Zena Ronald Peet as Playwright Sharon Brown as Liz Reddick-Lawrence Character / Latisha Jeremy Holm as Duncan Herz Lance Roberts as Adrian Boseman Character / Adan Co Starring Kineta Kunutu as Young Woman Emma Geer as Barnard Student Uncredited John Larroquette as Gavin Firth