Guest Stars Daniel K. Isaac as Ben Kim Kelly AuCoin as "Dollar" Bill Stearn Dan Soder as Dudley Mafee Keith Eric Chappelle as Everett Wright Christopher Denham as Oliver Dake Susan Misner as Terri McCue Jack Gilpin as Sean Ayles David Strathairn as Jack Foley Mike Birbiglia as Oscar Langstraat Tom Lipinski as Tim Dones Brian Wiles as John Sean Patrick Reilly as Senator Joe Scolari Michael Kostroff as Mick Nussfaur Siobhan Fallon as Trustee Jordan Lage as Minor Welles Co Starring Zina Wilde as Helena Kira Visser as Donna Chris Carfizzi as Rudy Ian Blackman as Earl Willis Steve Gagliastro as Ronnie Jack Davidson as Class of '68 President Austin Ku as Salesperson Monte Berger as Classmate