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 Rob Morrow as Adam DeGiulio Christopher Denham as Oliver Dake David Strathairn as Jack Foley Mike Birbiglia as Oscar Langstraat Tom Lipinski as Tim Dones Brian Wiles as John Obi Abili as Roland Aduba Co Starring Zina Wilde as Helena Chris Carfizzi as Rudy Jerry D. O'Donnell as Security Guard (Jerry) Melanie Hinkle as Bronwen Adit Dileep as Roger Bisserat Tseggai as Waitress Vincent Beard as Assistant US Attorney Wylie Dufresne as Himself