Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Bitty Schram Sharona Fleming Actor Jason Gray-Stanford Lt. Randall Disher Actor Ken Marino Lester Highsmith Guest Star Melora Hardin Trudy Monk Guest Star Jeremy Roberts Dewey Albert Guest Star Nate Mooney Scat Guest Star Dwayne Barnes Officer Cooper Guest Star James Intveld Undercover Cop Guest Star Grant Garrison Officer Hensley Guest Star Nick Spano Officer Salvatore Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Lance Krall Salvatore - Car Salesman Guest Star Meredith Roberts Quill Burger Girl Guest Star Randy Zisk Director Tom Scharpling Writer Chuck Sklar Writer