Movie: The Thomas Crown Affair (1968)

No movie better captures the reasons why folks refer to him as "The King of Cool." McQueen plays Thomas Crown, a billionaire that's bored of life, so he decides to pull heists just for kicks. He pushes the navy blue Rolls-Royce to pick up the cash at drop off points in the beginning and at the end of the movie. Shadow Coupes were built to order and this one had a standard 6.2-liter V8 engine with plush leather interior and all-power everything.