The plot: Enigmatic Boston real estate tycoon Thomas Crown (Steve McQueen in the 1968 version) has a lucrative secret pastime: He's robbing a bank. Not himself, of course; instead, he choreographs a team of five total strangers through the theft he has intricately timed and researched. Crown hardly needs the money; it's the rush he's after. On the hook for the stolen $2.6 million, the bank's insurance company sends investigator Vicki Anderson (Faye Dunaway) to solve the case. She immediately suspects Crown and just as quickly falls for his charms. Or does she merely pretend to in hopes of landing her own fat payday? Ah, whom to trust?
Why it's worthy: "In 'The Thomas Crown Affair,' nobody cares about the central story really; it's all about Steve McQueen and Faye Dunaway," says Pelecanos. Indeed, the cat-and-mouse game between the 38-year-old McQueen and the 27-year-old Dunaway makes for movie magic, as in this early scene:
Crown: "What a funny, dirty little mind."
Anderson: "It's a funny, dirty little job."
Crown: "Think you'll get me?"
Anderson: "I hope so."
Set notes: Most romantic chess game scene ever. The 1999 Pierce Brosnan-Rene Russo remake lacks the playful romantic chemistry.