Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Bitty Schram Sharona Fleming Actor Jason Gray-Stanford Lt. Randall Disher Actor Enrico Colantoni Joe Christie Guest Star Patrick Thomas O'Brien Brent Donovan Guest Star Alanna Ubach Jennie Silverman Guest Star Kane Ritchotte Benjy Fleming Guest Star Maree Cheatham Edna Coruthers Guest Star Michael Weston Morris Guest Star Kyle Davis Ronnie Guest Star Esther Scott Delores Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Sharon Johnston Clara Guest Star Jill Wagner Crystal Guest Scott Foley Director Ross Abrash Writer