Guest Stars Brett Cullen as James Rose Abdoo as Mrs. Monk Susan Ruttan as Mrs. Ledsky Emma Degerstedt as Beth Donna Bullock as Sherry Judd Katelyn Pippy as Young Sherry James C. Burns as Scary Biker Kevin G. Schmidt as Leo Grant Rosenmeyer as Young Adrian Monk Jeannie Epper as Gladys Karl T. Wright as Principal Thicket Beau Dremann as Uniform Cop at Bar 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