Annie Hall (1977)

Annie Hall (1977) shattered romantic comedy conventions, earning four Academy Awards including Best Picture — a feat 50% more impressive than any other comedy on this list in terms of major awards won. Woody Allen's direct-to-camera dialogue and nonlinear narrative cost $4 million and grossed $38 million worldwide. It launched Diane Keaton's Annie Hall look as a global fashion trend, outselling #3's wardrobe influence by a factor of 10 in 1977 retail figures.