The Thomas Crown Affair (1999)

Plot: Competitive New York mergers and acquisitions king Thomas Crown steals a Monet for the challenge only to be fingered as the thief within two days by insurance investigator Catherine Banning who's smart, driven, and alone. Ostensibly she works with the police but in truth she runs her own show playing cat and mouse with Crown. Soon it's a romance: a black and white ball, a glider flight, two days in Martinique. Back in Manhattan, she thinks she has reason to be jealous, so when he suggests they go off together, she hesitates. He may have more tricks up his sleeve and, as his psychiatrist has asked him, what would it take for him to trust a woman and, in turn, be trusted?

Alternative Plot: Bored billionaire Thomas Crown (Pierce Brosnan) decides to entertain himself by stealing a Monet from a reputed museum. When Catherine Banning (Rene Russo), an investigator for the museum's insurance company, takes an interest in Crown, a complicated back-and-forth game with romantic undertones begins between them. In an attempt to find out where Banning's loyalties lie, Crown returns the painting and essentially turns himself in, hoping that Banning's feelings for him will lead to an escape.

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