Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Misha Collins Michael Karpov Guest Star Mini Anden Natasia Zorelle Guest Star Dana Ivey Mrs. Eels Guest Star Jimmy Palumbo Mr. Gorman Guest Star Emmy Clarke Julie Teeger Guest Star Susan Ruttan Mrs. Ledsky Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Gregg Daniel Truck Driver Guest Star Bob Jesser Armored Car Driver Guest Star Chet Grissom First Detective Guest Star Robert Catrini Teddy Mulligan - Informant Guest Star Aaron Lustig Prosecutor Fox Guest Star Morgana Davis Female Paramedic Guest Star Keith Oney Local Mechanic Guest Star Rose Abdoo Mrs. Monk Guest Star Karl T. Wright Principal Thicket Guest Star Randy Zisk Director Andre Belgrader Director Philip Casnoff Director Jerry Levine Director Robert Singer Director Jefery Levy Director Eric Laneuville Director Anthony R. Palmieri Director Stephen Surjik Director David Breckman Writer Joe Toplyn Writer Tom Scharpling Writer Daniel Dratch Writer Hy Conrad Writer Jack Bernstein Writer Nell Scovell Writer Liz Sagal Writer Andy Breckman Writer Peter Wolk Writer Jonathan Collier Writer