Andy Breckman Creator, Writer Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Virginia Madsen T.K. Jensen Guest Star Melora Hardin Trudy Monk Guest Star Casper Van Dien Lt. Steven Albright Guest Star Craig T. Nelson Ana Teresa Sosa Guest Star Emmy Clarke Julie Teeger Guest Star Erich Anderson John Buxton Guest Star Chandra West Carolyn Walsh Guest Star Michael Stoyanov Stephen Dorn Guest Star Michael Patrick McGill Sgt. Steiner Guest Star Tim Bagley Harold Krenshaw Guest Star DB Woodside Dr. Matthew Shuler Guest Star Héctor Elizondo Dr. Neven Bell Guest Star Jessica McCabe Teenage Cashier Guest Star Mary Beth Evans Mrs. Rickover Guest Star Michael Coleman Uniform Cop 1 Guest Star Shelly Cole Mrs. Rickover Guest Star Randy Zisk Director Kevin Hooks Director Dean Parisot Director Tawnia McKiernan Director Mary Lou Belli Director Jerry Levine Director Joe Pennella Director Josh Siegal Writer Joe Toplyn Writer Tom Scharpling Writer Hy Conrad Writer Jack Bernstein Writer Michael Angeli Writer Salvatore Savo Writer Joe Ventura Writer Peter Wolk Writer Beth Armogida Writer Dylan Morgan Writer