Guest Stars Brenda Braxton as Madeline Gilford Joshua Echebiri as Devin Wallace Shawn as Charles Lester Alok Tewari as Osman Bin Ansari Anthony Cochrane as James Winston Ben Shenkman as Ben-Baruch Danny Burstein as William Schultz Michael Thomas Holmes as Horace Carruthers Richard Kind as Judge Alan Davies Audrie Neenan as Judge Marion Handgrove Chelsea Lee Williams as Lynette Moti Margolin as Gal Avivi Justin Withers as Darius Kevin Bernard as Crazy Man Emana Rachelle as Associate Gabby Ryann Redmond as Willow Dormer Laura Shoop as Liza Gabriel Brown as Kahill Michael Hayden as Attorney