Guest Stars Tamberla Perry as Judge Charlotte Hazlewood Rachel Nicks as Rosalyn Brock Mike Pniewski as Frank Landau Chasten Harmon as Bianca Skye Carson Elrod as Josiah Nile Anastacia McCleskey as Associate Opal Rob Reiner as Judge Josh Brickner Lee Tergesen as Mr. Pezner Lorraine Toussaint as Nia Rogers Rachel Dratch as Linda Shuck Christiani Pitts as Melanie Evers Johanna Day as Dr. Lola Pell Dana Aliya Levinson as Sadie Lipton Co Starring Marianna McClellan as DNC Associate Catharine Daddario as Piper Vega