The Thomas Crown Affair (1968)

Bored millionaire Thomas Crown (Steve McQueen) concocts and executes a brilliant scheme to rob a bank without having to do any of the work himself. When Vicki Anderson (Faye Dunaway), an investigator for the bank's insurance company, takes an interest in Crown, the two begin a complicated cat-and-mouse game with a romantic undertone. In an attempt to decipher Anderson's agenda, Crown devises another robbery like his first, wondering if he can get away with the same crime twice.