Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Brad Hunt Kris Kedder Guest Star Amara Zaragoza Kendra Frank Guest Star Benita Telles Annie Guest Star Craig Figueiredo Security Officer Guest Star Jon Kyle Hansen Jared Stottlemeyer Guest Star Terry Fradet Stork Guest Star Cameron Bunce Guy Freak Guest Star Hal Havins Maintenance Guy Guest Star James Logan Roadie Guest Star Jeffrey M. Bell Red Cross Volunteer Guest Star Randy Zisk Director Blair Singer Writer