Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Andy Richter Hal Tucker Guest Star David Eigenberg Tim Hayden Guest Star Emmy Clarke Julie Teeger Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Stephanie Erb Gail Segalis Guest Star Tom Yi Michael Kin Guest Star Al Rondon Heavyset Man Guest Star Dan Arnold Detective Kramer Guest Star Dan McNeill Face-Painted Man Guest Star Jon Crowley Surly Fan Guest Star Randy Zisk Producer Andy Breckman Writer Daniel Gaeta Writer