Unexpected Comedy: The Five Funniest Best Picture Winners
It’s Oscar time again, which means that Hollywood, and we their obedient servants, will pretend that the five movies we collectively disliked the least are the "best." It also means that the most somber, humorless movie will be crowned a masterpiece.
In the minds of Oscar voters, pleasure while viewing a movie–especially pleasure that manifests itself as laughter–automatically means that the movie is not serious enough to be any good. Even with these deeply cynical and annoying-at-Oscar-party beliefs, I was still dumbfounded at how few actual comedies won best picture, even ones masquerading as serious dramas.
Annie Hall (1977)
Hi! I’m a funny, short guy, and I’m a big fan of Annie Hall. Mom always told me I was a complete original, and I think this pretty much proves it. I have about two books worth of material to write about this particular movie, easily in my top five of all time, but I’ll just say that I’m shocked at how fresh and funny it's stayed in the 32 years since its release. This is impressive because it’s always been Woody’s most culturally relevant movie, as if he, for once, was actually paying attention to what was happening in the world around him instead of gently parodying his own fantasy Manhattan.
Before he locked himself in his Upper West Side tower and started creating a fabulist world where 12-year-olds are quoting Camus and 50 year old Manhattanites are more worried about Mahler than real estate, he listened to the street and what people were saying. Sometimes, it was hilarious, like sneezing in the cocaine. Sometimes, it was sour, like mocking Shelley Duvall’s reporter character as representative of everyone who likes rock music.
Comedies tend to lose their punch as the world they’re responding to fades into history, but Annie Hall always seems to be reacting to right now.





