Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Bitty Schram Sharona Fleming Actor Jason Gray-Stanford Lt. Randall Disher Actor Glenne Headly Karen Stottlemeyer Guest Star Stellina Rusich Trudy Monk Guest Star Kurt Fuller Dennis Gammill Guest Star Jim Jansen Mayor Rudner Guest Star Patrick Cranshaw Miles Hollings Guest Star Bill Erwin Hiram Hollings Guest Star Sonya Eddy Opal Guest Star Ralph Peduto Gravedigger Guest Star Alfred Dennis Old Man Guest Star Don Perry Newly Arrived Old Man Guest Star Kevin Dunigan Guard Guest Star Hira Ambrosino Reporter Guest Star Audrey Wasilewski Caucasian Nurse Guest Star Daniel Dratch Writer Lawrence Trilling Director Hy Conrad Writer