Guest Stars Asia Kate Dillon as Taylor Mason Kelly AuCoin as "Dollar" Bill Stearn Jeffrey DeMunn as Chuck Rhoades, Sr. Dan Soder as Dudley Mafee Ben Shenkman as Ira Schirmer Glenn Fleshler as Orrin Bach Ilfenesh Hadera as Deb Kawi Christopher Denham as Oliver Dake Malachi Weir as Lonnie Watley Eric Bogosian as Lawrence Boyd Arthur Nascarella as Bruno Capparelo Erinn Ruth as Mo Shaunette Renée Wilson as Stephanie Reed Michael Stoyanov as Terry Burke Kevin Breznahan as Johnny Burke Tony Yazbeck as Marc Capparello Richard Thomas as Sanford Bensinger Ross Partridge as Tom McKinnon Richard Topol as Angel James Wolk as Craig Heidecker Ian Kahn as Attorney General's Man Melissa Navia as Elena Gabriel Co Starring Daniel K. Isaac as Ben Kim Zina Wilde as Helena Kira Visser as Donna Brian Berrebbi as Randy Kornbluth Mark Cuban as Himself Quinn Franzen as Random Paralegal John Danaher as Instructor Dwelvan David as Caddy Jennifer Gottlieb as Trainer