Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Cynthia Stevenson Dianne Brooks Guest Star Franc Ross Clinic Doctor Guest Star Reginald VelJohnson Todd Guest Star Brian McNamara Kyle Brooks Guest Star Charles Rahi Chun Simon Guest Star Lindy Newton Younger Trudy Guest Star Luiggi Debiasse Younger Monk Guest Star Oliver Macready Drew Cooney Guest Star Alex Cohen Delivery Man Guest Star Charles Laulette Alumni Husband Guest Star Cutter Mitchell Uniform Cop Guest Star David Grossman Director Daniel Dratch Writer