Guest Stars Anika Noni Rose as Wendy Scott-Carr Carrie Preston as Elsbeth Tascioni Monica Raymund as Dana Lodge Rachel Hilson as Nisa Dalmar Jason Biggs as Dylan Stack Bob Balaban as Gordon Higgs Jennifer Ferrin as Elaine Middleton Rob Yang as Bao Shuwei Michael Lerner as Judge Dwight Sobel David Furr as Tom Landis Richard Topol as Alex Krakowski Brendan Titley as Crypto Barker #1 Jeremy Beiler as Crypto Barker #2 Gibson Frazier as Mitchell Tambor John Patrick Doherty as Crypto Barker #3 Jim Cramer as Himself