Guest Stars Laura Benanti as Quinn Tyler Phoebe Dynevor as Clare O'Brien Michael Urie as Redmond Ben Rappaport as Max Horowitz Kathy Najimy as Denise Heller Steven Good as Rob Davis Janeane Garofalo as Cass Dekennessy De'Adre Aziza as Azealia King Lesli Margherita as Lizalot Miller Elizabeth Stanley as Elizabeth Holmes Jennifer Cody as Rachel Dolezal Stephen DeRosa as Bernie Madoff Preston Truman Boyd as Billy McFarland Co Starring Delphina Belle as Nicole Brooks Glenn Fleary as Greg Joseph Frederick Allen as Austin Pinkner