Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor David Valcin Reggie Dennison Guest Star Lennie Loftin John DeLancy Guest Star Jimmy Palumbo Mr. Gorman Guest Star Emmy Clarke Julie Teeger Guest Star Frank Novak Marv Chastwick Guest Star D.J. Harner Mother Guest Star Yvans Jourdain Criminalist Guest Star Eric Artell Tommy Guest Star Sean McDermott Kevin Guest Star Skyler Gisondo Kyle Guest Star Gentry Sanz-Agero Eating Detective Guest Star Philip Casnoff Director Hy Conrad Writer