Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Brad Garrett 'Honest' Jake Phillips Guest Star Jack Carter Joseph Moody Guest Star Katherine Kendall Cassie Drake Guest Star Ivo Nandi Honest Ramone Guest Star Marty Ryan Mr. Sutton Guest Star Héctor Elizondo Dr. Neven Bell Guest Star Bob Gebert Hardware Store Clerk Guest Star Burl Moseley Police Officer Guest Star Cameron Meyer Mother Guest Star David Castellani Medical Examiner Guest Star McNally Sagal Pamela Moody Guest Star Randy Zisk Director Andy Breckman Writer Anthony Maranville Writer