Guest Stars Louis Cancelmi as Victor Mateo Glenn Fleshler as Orrin Bach Terry Kinney as Hall Susan Misner as Terri McCue Jack Gilpin as Sean Ayles Jerry O'Connell as Steven Birch David Cromer as Donnie Caan Dennis Boutsikaris as Kenneth Malverne Annapurna Sriram as Tara Mohr Kate Arrington as Maria Saldana John Ellison Conlee as Garth Sykes Penn Jillette as Himself Neal Huff as Bert Kroll Co Starring Daniel K. Isaac as Ben Kim Kelly AuCoin as "Dollar" Bill Stearn Dan Soder as Dudley Mafee Ilfenesh Hadera as Deb Kawi Zachary Unger as Kevin Rhoades Alexa Jacqueline Swinton as Eva Rhoades Brian Berrebbi as Randy Kornbluth Frank Harts as Dale Christo Sam Gilroy as Michael Dimonda Ivan Martin as Butch "The Pouch" Probert Jacob H. Knoll as Channing Feldt / Trader Ali Ahn as Carly Catherine A. Callahan as Lilly Smith Franco Gonzalez as Tito Cadden Jones as Birch's Lawyer Alex Cranmer as Chadwick Eads Angela Oh as Marissa Compliance Ezra Knight as Steve Compliance Zefralyn Osborn as Masseuse Parker Pogue as Ellis Eads Michaela Sprague as Fiona Charles Glaser as Eads, Sr.