Month of Movies: Oscar-Winning Comedies to Make You Laugh

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Oh, it's a tale as old as the trolley tracks buried under Wilshire Boulevard. Oscar and comedy. Comedy and Oscar. You two just can't seem to make this thing work, can you? Once upon a time you were grand old pals, lovers, even -- the musicals, the comedies, the slapstick. The delicate craft of making people laugh; all held up high alongside the work of their dramatic counterparts, and awarded handsomely with Oscar gold.

Fast forward to present day. We're just dusting ourselves off from the Great Recession. 2010 was a year that I expected to see a bit more levity in theaters -- or at least a little more nail-biting dramedy a la Focus Features' The Kids Are All Right -- but instead we're looking at a roster of riveting, brilliant, prophetic, but holy crap are they a bunch of twisted, disturbing, dark, and depressing flicks.

I mean, sure -- maybe not Toy Story 3, but you're totally lying if you say that movie didn't make you cry.

It's been hotly debated for years whether or not comedies should be split off into a separate category, and I'll turn it over to SF Chronicle Critic Mick LaSalle, because his answer to that very question hits the crux of the issue, and, maybe it's inappropriate, but I'd be remiss if I didn't acknowledge that his use of the word "ghettoizes" made me chuckle. It's true though.

I have mixed feelings. I think comedies and comic acting deserve acknowledgment but that establishing separate categories ghettoizes them. Separation implies inequality.

It's worth noting though, that the Golden Globes do separate films into two categories -- Dramatic and Musical or Comedy.

So, in honor of the fact that the greatest thing a movie can do to entertain me is make me really, wholeheartedly, forget-it-all laugh, I'm going to harken back to the days when Oscar was an equal opportunity booty-kisser. Here are a few of the greatest comedies to take home the gold.

  • Frank Capra's 1938 Best Picture winner YOU CAN'T TAKE IT WITH YOU stars Drew's Great Great Great (or something) Grandpa Lionel Barrymore, and was based on the Pulitzer prize winning play of the same name.
  • Because I apparently loathe horses and love to beat them well after their dead, I'm mentioning yet again my favorite movie ever ALL ABOUT EVE -- a rather dark comedy for it's day -- which took home the Best Picture Statuette in 1950.
  • 1973's Best Picture Winner THE STING is a comedic crime caper starring a young and tasty Paul Newman and Robert Redford.
  • Jack Nicholson solidified his place as one of the greatest actors of his generation for his role in ONE FLEW OVER THE CUCKOO'S NEST, the1975 Picture of the Year.
  • ANNIE HALL. An American Classic. This Woody Allen/Dianne Keaton love story was 1977 Best Picture victor.
  • Okay, so it's kind of a dramedy, but the brilliant pairing of Morgan Freeman and Jessica Tandy clinched up DRIVING MISS DAISY as the Best Picture shoo-in of 1989.
  • FORREST GUMP is just...*sigh* What's not to get lost in about that movie? Sure the shrimpin' talk, and bad "box o' chocolate" impressions got annoying as all get out, but that didn't make the film any less worthy of it's 1994 Best Picture Win.
  • Possibly the lightest fare to take home the trophy in recent memory, SHAKESPEARE IN LOVE shocked pretty much everyone when it beat out SAVING PRIVATE RYAN for Best Picture in 1998.
  • Shakespeare in Love
    Image courtesy Miramax

  • AMERICAN BEAUTY. The pitch-black comedy from the mind meld of Sam Mendes and Alan Ball on the other hand, didn't surprise many when it snagged the award for Best Picture in 1999.

Okay, I could go on, but then I'd be giving you a full list of all of The Comedies that were deemed worthy of the Best Picture nod throughout Oscar history (hint: they include GIGI, TOM JONES -- and yet another of my favorites -- THE APARTMENT, and I think we're just about there.)

So what comedies do you think the Academy missed the boat on this year? And do you think comedy and drama should be split into separate categories? And also -- go tell us which film will take home the Oscar now!

Morgan (The818) is a blogger and screenwriter living in Los Angeles. She overshares her personal life - complete with curse words - at The818.com, talks art and design over at Cargoh.com, and tweets: @the818.

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