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 Kira Visser as Donna Zina Wilde as Helena Chris Carfizzi as Rudy Tijuana Ricks as Tonelle "T" Burton Daniel Boulud as Himself Raymond J. Lee as Leonard Shatzkin Arnold Younguk Kim as Judge #2 Christiana Blain as Elizabeth Curzon Dobell as Judge Go Diana Craig as Judge #3 Simon Pearl as Darren