Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Bitty Schram Sharona Fleming Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Kane Ritchotte Benjy Fleming Guest Star Mako Master Zi Guest Star Josh Stamberg Agent Grooms Guest Star Stanley Kamel Dr. Charles Kroger Guest Star Melora Hardin Trudy Monk Guest Star Emmy Clarke Julie Teeger Guest Star Matt Champagne Steve Marriot Guest Star Cleo King 911 Operator Guest Star Andreea Radutoiu Larysa Zeryeva Guest Star Scott DeFoe Uniform Cop Guest Star Tim Bagley Harold Krenshaw Guest Star John Maynard Repairman Guest Star Lance Krall Salvatore - Car Salesman Guest Star Carl Ciarfalio First Goon Guest Star Meredith Roberts Quill Burger Girl Guest Star Andre Belgrader Director Andy Breckman Writer David Breckman Writer Allison Liddi-Brown Director Scott Foley Director Anthony R. Palmieri Director Randy Zisk Director Joe Toplyn Writer Tom Scharpling Writer Hy Conrad Writer Nell Scovell Writer Ross Abrash Writer Lee Goldberg Writer Peter Wolk Writer Jerry Levine Director Michael Zinberg Director William Rabkin Writer Chuck Sklar Writer Daniel Dratch Writer