Tony Shalhoub Adrian Monk Actor Ted Levine Capt. Leland Stottlemeyer Actor Traylor Howard Natalie Teeger Actor Jason Gray-Stanford Lt. Randall Disher Actor Sarah Silverman Marci Maven Guest Star Sharon Lawrence Linda Fusco Guest Star John Mese John Ringel Guest Star Anne De Salvo Auctioneer Guest Star Jennifer Ann Massey Cameron Meyer Guest Star Joey Baldwin Young Clerk Guest Star Kelli Jackson Second Bidder Lady Guest Star Lisa Pedace First Lady Bidder Guest Star Anthony Santa Croce Heckler Guest Star Martin Taylor Brian Guest Star Michael Coleman Detective Guest Star Randy Zisk Director Andy Breckman Writer