Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Stanley Kamel Dr. Charles Kroger Guest Star Scott Glenn Sheriff Rollins Guest Star Tim DeZarn Max Barton Guest Star Snoop Dogg Murderuss , Russell Kroy Guest Star Emmy Clarke Julie Teeger Guest Star Melora Hardin Trudy Monk Guest Star Sharon Lawrence Linda Fusco Guest Star Courtney Gains Frank Nunn Guest Star Kurupt Himself Guest Star Dan McNeill Bartender Guest Star Diego DiGiovanni Italian State Trooper Guest Star Isabella Acres Other Child Guest Star Martin Taylor Brian Guest Star Horacio Galaviz Carwash Worker Guest Star Bradley James Prison Guard Guest Star Jay Powell Vagrant Guest Star Randy Zisk Director Anton Cropper Director Michael W. Watkins Director Wendey Stanzler Director Sam Weisman Director Jonathan Collier Director, Writer Andre Belgrader Director Joe Toplyn Writer Tom Scharpling Writer Hy Conrad Writer Daniel Dratch Writer Josh Siegal Writer Alan Zweibel Writer Salvatore Savo Writer Peter Wolk Writer Tom Gammill Writer Andy Breckman Writer Daniel Schofield Writer Dylan Morgan Writer