Guest Stars Brett Cullen as James Rose Abdoo as Mrs. Monk James C. Burns as Scary Biker Donna Bullock as Sherry Judd Susan Ruttan as Mrs. Ledsky Katelyn Pippy as Young Sherry Emma Degerstedt as Beth Grant Rosenmeyer as Young Adrian Monk Kevin G. Schmidt as Leo Jeannie Epper as Gladys Beau Dremann as Uniform Cop at Bar Karl T. Wright as Principal Thicket David Hunt as Michael Norfleet Shane Haboucha as Jimmy Daniel Riordan as Bartender Christopher Gerse as Stork Corbin Bronson as Information Clerk Michael Dunn as George James E. Thompson as School Janitor Zoe Keller as Lily Brent King as Travis