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 Allan Havey as Karl Allerd Christopher Denham as Oliver Dake Eric Bogosian as Lawrence Boyd Mike Birbiglia as Oscar Langstraat Seth Barrish as Dr. Ari Gilbert Tom Lipinski as Tim Dones Clifton Davis as Judge Wailand Brian Wiles as John Gia Crovatin as McKayla Matthew Humphreys as Walter Michael Cyril Creighton as Martin Yancy Co Starring Zina Wilde as Helena Kira Visser as Donna Chris Carfizzi as Rudy Tijuana Ricks as Tonelle "T" Burton Daniel Boulud as Himself Christiana Blain as Elizabeth Curzon Dobell as Judge Go Arnold Younguk Kim as Judge #2 Diana Craig as Judge #3 Raymond J. Lee as Leonard Shatzkin Simon Pearl as Darren