The Thomas Crown Affair (1968)

Four men pull off a daring daytime robbery at a bank, dump the money in a trash can and go their separate ways. Thomas Crown, a successful, wealthy businessman pulls up in his Rolls and collects it. Vickie Anderson, an independent insurance investigator is called in to recover the huge haul. She begins to examine the people who knew enough about the bank to have pulled the robbery and discovers Crown. She begins a tight watch on his every move and begins seeing him socially. How does the planner of the perfect crime react to pressure?