Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Bitty Schram Sharona Fleming Actor Jason Gray-Stanford Lt. Randall Disher Actor Adam Arkin Dale 'The Whale' Biederbeck Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Juan Chioran Dr. Charles Kroger Guest Star Max Morrow Benjy Fleming Guest Star Lucia Fillipone Louisa Guest Star Jennifer Pisana Sue Ellen Guest Star James Downing Police Dispatcher Guest Star Quancetia Hamilton 2nd dispatcher Guest Star Amber Marshall Second girl Guest Star David Sparrow Sgt. Cargill Guest Star Faye Rauw Woman on monitor Guest Star Liise Keeling Judge Lavinio Guest Star Paul-Emile Frappier Man in Reception Guest Star Hrant Alianak Judge Hackman Guest Star Robert C. Thompson Director Andy Breckman Writer