Thomas Crown (Steve McQueen) is a self-made Boston millionaire who 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. Erwin Weaver (Jack Weston) leads the cast of crooks who never actually meet Crown but manage to pull off the robbery without a hitch.
Crown deposits 3 million in a Swiss bank account, pays off the crooks, and waits for the insurance company to repay the bank for the loss. Eddy Malone (Paul Burke) is the savvy detective who helps insurance investigator Vicky Anderson (Faye Dunaway) find the mastermind behind the heist.
Thomas Crown Affair became one of the first films to employ many split-screen images throughout its running time, as devised by editor Hal Ashby. Michel Legrand's score was nominated for an Academy Award, and the song The Windmills Of Your Mind, written by Legrand with Alan and Marilyn Bergman took home the coveted Oscar.