A ranking by Brooks Rich Now we come to the other end of the Best Picture spectrum. There are different ways to judge these films. Some are just downright awful in my opinion. Others are fine but did not deserve over other films. Best Pictures should be big, have a feeling of grandeur and importance. So here are the worst films to win Best Picture. 20. Gone With the Wind (1939) Controversy right out of the gate. It might be not be the worst film of all time but Gone With the Wind is an endless maudlin film that won Best Picture over a truly deserving timeless classic, The Wizard of Oz. The films lower on the list may not be technically awful but they won over something more deserving. I personally can't stand Gone With the Wind, it never ends it seems, but I understand that some people like it and it might have it's place. But over Wizard of Oz? Come on. Gone With the Wind goes down as one of those big crowd pleasers of the time that hasn't aged well. 19. Argo ...