Guest Stars Brenda Braxton as Madeline Gilford Zach Grenier as David Lee Samaria Nixon-Fleming as Paralegal Louisa Phillip James Brannon as Kevin Walker Rashad Edwards as Jim / Mail Room Clerk Jordan Boatman as Associate Lucy Daniel Breaker as Randy Elkin Alok Tewari as Osman Bin Ansari 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 Thomas Middleditch as Kyle Vespertine-Kalepark Joanna Gleason as Judge Carmella Romano Nick Kohn as Court Official Dennis Staroselsky as Officer Wallace Travis Przybylski as Oliver the Guard Cade Burk as White Supremacist