Guest Stars Daniel K. Isaac as Ben Kim Kelly AuCoin as "Dollar" Bill Stearn Dan Soder as Dudley Mafee Stephen Kunken as Ari Spyros Ben Shenkman as Ira Schirmer Glenn Fleshler as Orrin Bach Keith Eric Chappelle as Everett Wright Jack Gore as Gordie Axelrod Danny Strong as Todd Krakow Zachary Unger as Kevin Rhoades Clancy Brown as Waylon 'Jock' Jeffcoat Christopher Denham as Oliver Dake Jerry O'Connell as Steven Birch David Strathairn as Jack Foley Clara Wong as Mistress Gia Crovatin as McKayla Dennis Boutsikaris as Kenneth Malverne Co Starring Zina Wilde as Helena Kira Visser as Donna Chris Carfizzi as Rudy Alexa Jacqueline Swinton as Eva Rhoades Brian Beckerle as Dean Axelrod Brian Berrebbi as Randy Kornbluth Tijuana Ricks as Tonelle "T" Burton Sean Ringgold as Security Guard Quinn Franzen as Random Paralegal Marisa Brau-Reyes as Carrie (Babysitter) Randall Miles as Martin Carlisle Marc Lasry as Himself Dierdre Reimold as Stunner Marlene Ginader as Waitress Miller Tai as AUSA Omeed Malik as Omar Malkov Charles Koppelman as Cameron Stoldt Perry Weitz as Gary Lanzo Michael Adam Karsch as Himself Damian Muziani as Russian Asshole Michael Platt as Himself