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 Richard Topol as Alex Krakowski David Furr as Tom Landis Rob Yang as Bao Shuwei Michael Lerner as Judge Dwight Sobel 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