Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Stanley Tucci David Ruskin Guest Star Paul Blackthorne Dr. Polanski Guest Star Reginald VelJohnson Todd Guest Star Stephen Bogardus Derek Bronson Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Emmy Clarke Julie Teeger Guest Star Drew Powell Eddie Murdoch Guest Star Anne Gee Byrd Mrs. Kennedy Guest Star Dan Arnold Detective Kramer Guest Star Gary Sievers First Fireman Guest Star Alex Cohen Delivery Man Guest Star Dan McNeill Face-Painted Man Guest Star Craig Patton Rent-A-Cop Guest Star John Berg Guest Alfred Guest Star Drew Matthews Third Orphan Guest Star Ken Barnett Deputy Hatcher Guest Star Randy Zisk Director, Producer Andre Belgrader Director Andy Breckman Writer Chris Long Director Wendey Stanzler Director Stephen Surjik Director Jerry Levine Director Tom Scharpling Writer Hy Conrad Writer Daniel Dratch Writer Jack Bernstein Writer Josh Siegal Writer Lee Goldberg Writer Blair Singer Writer Jonathan Collier Writer Daniel Gaeta Writer Joe Toplyn Writer Dylan Morgan Writer William Rabkin Writer