Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor DJ Qualls Rufus - Computer Geek Guest Star Tyler Mane Dirk - Motorcycle Rider Guest Star Davenia McFadden Gladys Menchen Guest Star Ryan Alosio Warren Landis Guest Star Jamie Anne Allman Jennie Mandeville Guest Star Faran Tahir Museum Official Guest Star Daniel Browning Smith Danny Chasen Guest Star Derrick O'Connor Inspector St. Clare Guest Star Stanley Kamel Dr. Charles Kroger Guest Star James Wing Woo Kwan Guest Star Carissa Koutantzis Cashier Guest Star Randy Zisk Director Tom Scharpling Writer Daniel Dratch Writer