Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Tim Bagley Harold Krenshaw Guest Star Emmy Clarke Julie Teeger Guest Star Cyd Strittmatter Clarissa Guest Star David Koechner Joey Krenshaw Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Colleen Crabtree 2nd Duty Nurse Guest Star Connor Gibbs Little Boy Guest Star Cynthia Hartzell Kindergarten Teacher Guest Star Devon Kelly Excited Fan Guest Star Henry Dittman Second Fan Guest Star Kesun Loder Jimmy Krenshaw Guest Star Jonathan Collier Director Alan Zweibel Writer