Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Jeffrey Donovan Steve Wagner Guest Star Eric Allan Kramer Darrell Cain Guest Star Emmy Clarke Julie Teeger Guest Star Brianna Brown Joanne Raphelson Guest Star Michael Belcher Bobby Guest Star Ariel Winter Donna Cain Guest Star Natasha Pavlovich Nicole Wagner Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Al Malafronte Congressman Guest Star Billy Mayo Mechanic Guest Star Brandon Matthew Parker First Boy Guest Star Randy Zisk Director David Breckman Writer Joe Toplyn Writer