Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Casper Van Dien Lt. Steven Albright Guest Star William Atherton Commander Nathan Whitaker Guest Star La Monde Byrd Petty Officer Wedoes Guest Star Rob Evors Petty Officer Kramer Guest Star Héctor Elizondo Dr. Neven Bell Guest Star Dan McNeill Passing Sailor 1 Guest Star Pepper Sweeney Navy Cook Guest Star Tom Nagel Passing Sailor 2 Guest Star Scott MacDonald Chief of Boat Guest Star Paris Barclay Director Jack Bernstein Writer