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 Shaunette Renée Wilson as Stephanie Reed Erinn Ruth as Mo Kevin Breznahan as Johnny Burke Michael Stoyanov as Terry Burke Tony Yazbeck as Marc Capparello Richard Thomas as Sanford Bensinger Richard Topol as Angel Ross Partridge as Tom McKinnon 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