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 Glenne Headly Karen Stottlemeyer Guest Star Kane Ritchotte Benjy Fleming Guest Star Kane Richotte Benjy Fleming Guest Star Chane't Johnson First Teacher Guest Star Jimmy Shubert Frank Pulaski Guest Star David Doty O'Dell Guest Star Gary Kraus Entry Guard Guest Star David Stanford Uniform Cop Guest Star Damara Reilly Female Guard Guest Star Clint Culp Barfly Guest Star Lance Krall Floppy the Clown Guest Star Hira Ambrosino Reporter Guest Star Josh Stamberg Agent Grooms Guest Star Susan Chuang Kathleen Guest Star Candice Michelle Sapphire Model Guest Star David Breckman Writer Daniel Dratch Writer Michael Angeli Writer Lee Goldberg Writer Randy Zisk Director, Producer Jerry Levine Director Tom Scharpling Writer Lawrence Trilling Director Craig Zisk Director William Rabkin Writer Michael Alan Spiller Director Ron Underwood Director Wendy Mass Writer Rick Kronberg Writer Hy Conrad Writer Stu Levine Writer Andy Breckman Writer, Executive Producer Hugo Cortina Cinematographer