Guest Stars Brenda Braxton as Madeline Gilford Zach Grenier as David Lee Samaria Nixon-Fleming as Paralegal Louisa Phillip James Brannon as Kevin Walker Jordan Boatman as Associate Lucy Rashad Edwards as Jim / Mail Room Clerk Alok Tewari as Osman Bin Ansari Daniel Breaker as Randy Elkin Anthony Cochrane as James Winston Phylicia Rashad as Renetta Clark John Benjamin Hickey as Neil Gross Keith Randolph Smith as John Wilson Shahar Isaac as Zev Beker Gregory Connors as Bearded Man Shuler Hensley as Buck Burns Joanna Gleason as Judge Carmella Romano Thomas Middleditch as Kyle Vespertine-Kalepark Nick Kohn as Court Official Travis Przybylski as Oliver the Guard Dennis Staroselsky as Officer Wallace Cade Burk as White Supremacist