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.

Shakespeare in Love (1998)

Like Romeo and Juliet, the play the movie parallels, Shakespeare in Love’s strength is not the love story. Of course, seeing it in the theater was a great chance to experience the singular Shakespearean experience of listening to jackasses laughing at jokes in a way that says "I'm a smart person, and cultured too! Did you hear that pun on the word coal? It references a 16th century torture device that is similar to the stocks! That shit be funny, yo!"

But Shakespeare in Love is actually very funny in a way that combines early Woody Allen absurdism with (Shakespeare on the couch) an inherent knowledge of Shakespearean word play and history that almost certainly is the product of co-screenwriter Tom Stoppard.  It's closer to the heart of Shakespeare's true sense of humor that anything that schmuck Kenneth Branagh could ever hope to do.

Forrest Gump (1994)

Forrest Gump is a funny movie despite its instinct to be a mawkish, manipulative piece of crap. What stands out most watching it now is how gifted a comic actor Tom Hanks can be, something it's easy to forget when he's constantly being shot by Nazis in Philadelphia.

Even though he's playing a mentally-challenged person of conveniently vague diagnosis, Hanks does not rely on simple mimicry and mannerisms to carry him to Oscar glory. He makes the character of Forrest Gump work because he knows that the key to the comedy here is making the deadpan seem profound. Of course, Woody Allen did a lot of this in Zelig, but that's besides the point.

There might come a day when I can say I actually enjoy watching Forrest Gump, but I'm not afraid to admit that it makes me laugh more and more each time I watch it, which is all the time because it's always on cable and I don't leave the house all that much.

The Apartment (1960)

Consider it the Mad Men of it's time, but actually commenting on the culture of its time.  It's a lot more frank about adultery, ambition and the caddishness of men in the business world (or any world) than fuzzy history would acknowledge. Like a lot of comedies pre-1970, it feels like a comedy in tone and manner, especially in the first half, but didn't really make me laugh all that much.  In fact, Jack Lemmon's annoying mannerisms and the faux-frothiness of the repartee turned me off until Shirley MacLaine took over the story. She gives a poignant, believable performance as a woman not only suffering heartbreak but lost identity. She's funny and kind of puts Lemmon's work as Twitchy McGee to shame. It's not the funniest movie, at least not anymore, but it's much better than the overrated and trying too hard Some Like it Hot.

You Can't Take it With You (1938)

I'd just like to put in a word for You Can't Take It With You as the stand-in for all of the frizzy, screwball comedies of the 30's and 40's that didn't luck out and win the Best Picture Oscar. The Miracle of Morgan's Creek, His Girl Friday, The Thin Man among others still hold up very well, and though they weren't the ponderous, heavy-handed melodramas that were so popular in their time (and still are, in hipper guises) they are lot more fun to watch than a lot of the other so-called classics.

I'm not sure that any other film classified definitively as a comedy won the Best Picture until Annie Hall–though The Apartment may have been technically called a comedy. Really, Academy? What are you afraid of? Fart jokes in The English Patient? Dancing dildos in Driving Miss Daisy? Actually, that would be awesome.