Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Reed Diamond FBI Agent Stone Guest Star Kelly Carlson Lola Guest Star Vincent Curatola Jimmy Barlowe Guest Star Tim Bagley Harold Krenshaw Guest Star Eric Balfour Lenny Barlowe Guest Star Louis Lombardi Tommy G. Guest Star Michael Fairman Stanley Greenblatt Guest Star Lance Barber Bill the Deliveryman Guest Star Hope Banks Young Agent Guest Star Joshua Grenrock Alvin Greenblatt Guest Star Kenyon Glover Doorman Guest Star Randy Zisk Director Salvatore Savo Writer