The Thomas Crown Affair (1968)

A self-made Boston millionaire Thomas Crown (Steve McQueen) masterminds a bank heist in hopes of leaving it all behind. Tired of being part of the Establishment, he has hopes of pulling off the caper and flying to Rio. The cast of crooks lead by Erwin Weaver (Jack Weston) manage to pull off the robbery without a hitch and without ever actually meeting Crown. After depositing 3 million into a Swiss bank account and paying off the crooks, Crown waits for the insurance company to repay the bank for the loss. With the help of savvy detective Eddy Malone (Paul Burke), insurance investigator Vicky Anderson (Faye Dunaway) attempts to find the mastermind behind the heist.