Gambit (1966)

Harry Dean (Michael Caine) is a career burglar set on stealing a piece of priceless art from the world's wealthiest man, Mr. Shahbandar (Herbert Lom). With the help of exotic showgirl Nicole Chang (Shirley MacLaine), he concocts the perfect scheme for how the robbery should go and lays it out point by point. However, when the team tries to execute the plan, perfection and reality don't quite match up, and Harry's vision begins to unravel in this twisty tale of a heist gone wrong.