The Thomas Crown Affair (1968) was directed and produced by Norman Jewison. The stars are Steve McQueen and Faye Dunaway.
McQueen plays Thomas Crown, a very wealthy man who stages a bank heist near his mansion in Boston for the thrill of it. Faye Dunaway plays Vicki, an insurance investigator, who suspects Crown but also finds herself falling in love with him.
The chess scene (above) happens at a crucial moment, after Crown invites Vicki to his mansion for the first time. As she explores his study (for clues?, because she is fascinated by this enigmatic man?), he watches from behind his chess set. He asks her, "Do you play?" and she responds "Try me."
The music for The Thomas Crown Affair, including this unforgettable sequence, was composed by Michel Legrand. Legend has it that Legrand, Jewison and editor Hal Ashby cut the picture and sound working together.
Near the end of his life, I met Hal Ashby. He was, and remains one of my favorite filmmakers. We never talked about this scene. I regret that.
For giggles: Here is the spoof of this scene from Austin Powers: The Spy Who Shagged me: