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 Max Morrow Benjy Fleming Guest Star Kane Ritchotte Benjy Fleming Guest Star Michael Gossack Reporter Guest Star Gail O'Grady Miranda St. Claire Guest Star Stellina Rusich Trudy Monk Guest Star J.C. Kenny Second Reporter Guest Star Ben Bass Gavin Lloyd Guest Star Rob LaBelle Sheldon Burger Guest Star David Sparrow Sgt. Cargill Guest Star Mary Black Mrs. Street Guest Star Shawn Reis Ian Sykes Guest Star Fred Ewanuick Jake Guest Star Roger Petersen First Reporter Guest Star Christopher Shyer Carl Guest Star Janet Wright Bonnie Guest Star Andy Breckman Writer Robert C. Thompson Director David M. Stern Writer Timothy J. Lea Writer Mitch Markowitz Writer Nick Marck Director John Romano Writer Siobhan Byrne O'Connor Writer Hy Conrad Writer Dean Parisot Director Kevin Inch Director David Breckman Writer Stephen Cragg Director Randy Zisk Director Adam Arkin Director Adam Davidson Director Tom Scharpling Writer Milan Cheylov Director Adam Shankman Director