Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Bitty Schram Sharona Fleming Actor Jason Gray-Stanford Lt. Randall Disher Actor Stanley Kamel Dr. Charles Kroger Guest Star Kane Ritchotte Benjy Fleming Guest Star Megan McKinnon Girl with a Cold Guest Star Gail O'Grady Miranda St. Claire Guest Star Stellina Rusich Trudy Monk Guest Star Michael Hogan Warren St. Claire Guest Star Ben Bass Gavin Lloyd Guest Star Rob LaBelle Sheldon Burger Guest Star Vincent Gale Jesse Goodman Guest Star Mary Black Mrs. Street Guest Star Shawn Reis Ian Sykes Guest Star Fred Ewanuick Jake Guest Star Christopher Shyer Carl Guest Star Dion Johnstone Lieutenant Gitomer Guest Star Janet Wright Bonnie Guest Star Andy Breckman Writer Dean Parisot Director