Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor J.P. Manoux Jacob Posner Guest Star Lucinda Jenney Zena Davis, Waitress Guest Star Terri Hoyos Maria Cordova Guest Star Tim Kang Mr. Brenneman Guest Star Andy Mackenzie Drug Dealer Guest Star Mary Chris Wall Home Shopping Salesperson Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Dan McNeill Bartender Guest Star Ed Fusco Other Taxi Driver Guest Star Jane Galloway Heitz Essie Guest Star Kent Karson Frat Kid Guest Star Randy Zisk Director David Breckman Writer