Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Bitty Schram Sharona Fleming Actor Jason Gray-Stanford Lt. Randall Disher Actor Andrew McCarthy Derek Philby Guest Star Kane Ritchotte Benjy Fleming Guest Star Rosalind Chao Arleen Cassady Guest Star Chane't Johnson First Teacher Guest Star Michael Reisz Second Teacher Guest Star Roz Witt Lunch Lady Guest Star James Martin Kelly Fire Marshal Guest Star Richard Alan Brown First Kid Guest Star Kristin Bryant Second Kid Guest Star Jennifer Record Girl Student Guest Star Erica Yoder Beth Landow Guest Star Jamie McShane Iverson, Grounds Keeper Guest Star David Rasche Coach Patterson Guest Star Bobby Brewer Kyle Guest Star David Breckman Writer Randy Zisk Director Rick Kronberg Writer Hy Conrad Writer