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13. A Clockwork Orange
A  dystopian crime film directed by Stanley Kubrick, its considered a masterpiece because of how far it pushed sex and violence on screen. Originally released as X-rated, Kubrick had to edit out one minute of especially explicit violence for it to be downgraded into an R-rating.

Seeing how the film explored how society dealt with people who were violent and rebellious, the fact that the film industry allowed it to be R-rated was important because it allowed future directors and writers to tackle these same uncomfortable but necessary scenes.