Special Guest Stars Alex Trebek as Himself Guest Stars Joe E. Tata as Nat Bussichio Kathleen Robertson as Clare Arnold Ann Gillespie as Jackie Taylor Jamie Walters as Ray Pruit Matthew Laurance as Mel Silver Nicholas Pryor as Chancellor Milton Arnold Bess Meisler as Rose Zuckerman Johnny Gilbert voices Himself Co Starring Paige Kettner as Erin Silver Ryanne Kettner as Erin Silver Daniel Henning as Jeopardy Contestant Stephanie Bader as 8 Year Old Andrea Janine Shiota as Jeopardy Representative Uncredited Chaton Anderson as Jeopardy Contestant