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 Shaunette Renée Wilson as Stephanie Reed Erinn Ruth as Mo 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 Kira Visser as Donna Zina Wilde as Helena Chris Carfizzi as Rudy Zachary Unger as Kevin Rhoades Jim Chanos as Himself David Neal Levin as Clarence Fiedler Angela Marie Roy as Shayleen McKinnon Merritt Janson as Bartender Phil Hellmuth Jr. as Himself Steve Tisch as Himself Ted Neustadt as Harry Bingham' Nicholas Baroudi as Hedge Guy Dared Wright as Innocuous Man