Guest Stars Daniel K. Isaac as Ben Kim Kelly AuCoin as "Dollar" Bill Stearn Dan Soder as Dudley Mafee Stephen Kunken as Ari Spyros Glenn Fleshler as Orrin Bach Terry Kinney as Hall Sarah Stiles as Bonnie Barella Keith Eric Chappelle as Everett Wright Clancy Brown as Waylon 'Jock' Jeffcoat Christopher Denham as Oliver Dake Jerry O'Connell as Steven Birch Gary Wilmes as FBI Agent Dancshazy John Malkovich as Grigor Andolov Mike Birbiglia as Oscar Langstraat Scott Aiello as Tommy Barkow Michael Aronov as Michael Corbin Bernsen as Bill McGann Brian Stokes Mitchell as Alvin Epstein Asa Somers as Ashley Cutler Co Starring Zina Wilde as Helena Kira Visser as Donna Chris Carfizzi as Rudy Kyle Anderson as FBI Partner #1 Sara Blakely as Herself David Kubicka as Dave the Bartender Keith Hernandez as Himself