Guest Stars Asia Kate Dillon as Taylor Mason Kelly AuCoin as "Dollar" Bill Stearn Dan Soder as Dudley Mafee Terry Kinney as Hall Danny Strong as Todd Krakow Christopher Denham as Oliver Dake Malachi Weir as Lonnie Watley Eric Bogosian as Lawrence Boyd Harry Lennix as Franklin Sacker Erinn Ruth as Mo Shaunette Renée Wilson as Stephanie Reed Marc Kudisch as Dr. Lenny Gustaferson Gia Crovatin as McKayla Ross Partridge as Tom McKinnon Shannon Koob as Marriage Counselor Sara Sampaio as Prianca Co Starring Daniel K. Isaac as Ben Kim Zina Wilde as Helena Kira Visser as Donna Chris Carfizzi as Rudy Zachary Unger as Kevin Rhoades Angela Marie Roy as Shayleen McKinnon David Neal Levin as Clarence Fiedler Jim Chanos as Himself Dared Wright as Innocuous Man Merritt Janson as Bartender Nicholas Baroudi as Hedge Guy Phil Hellmuth Jr. as Himself Steve Tisch as Himself Ted Neustadt as Harry Bingham'