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