The Italian Job (1969)

Car: 1968 Austin Mini Cooper

The original Italian Job featured another style icon, actor Michael Caine, alongside a fleet of one of history's most influential cars, the Mini Cooper. With its innovative, space-saving front-wheel-drive layout, the Mini Cooper influenced an entire generation of car manufacturers. The car was so important to the plot of the movie that its producers turned down a fleet of free Fiat vehicles, opting to pay for the majority of its Mini vehicles instead. The film's poster uses both the British and Italian flags in its design. It also features Mr. Caine's handsome mug super-imposed over an image of the iconic cars.