Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Bitty Schram Sharona Fleming Actor Jason Gray-Stanford Lt. Randall Disher Actor Max Morrow Benjy Fleming Guest Star John Bourgeois Commissioner Harry Ashcombe Guest Star Linda Kash Dolly Flint Guest Star Dean Monroe McKenzie PR Spokesperso Guest Star Bill Lake Hardware Owner Guest Star Andrew Gillies Daniel Guest Star J.C. Kenny Second Reporter Guest Star Julian Tassielli Uniformed Cop Guest Star Bryan Hatt Clerk Guest Star Jenny Levine Jennifer Zepetel Guest Star Kate Trotter Kate Ashcombe Guest Star Roger Petersen First Reporter Guest Star John Romano Writer Kevin Inch Director