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Top 15 Worst Oscar Performances
 319  6.6  7 Won: actress in a leading role - Cher
The horrid outfit Cher wore to the Oscars is more memorable than her performance. Or this movie, for that matter. ranna's rating:
 
2481 8.1 8.5 Won: actor in a leading role - Roberto Begnini
Should have won: Edward Norton from American History X A bad comedian tries to make "an artistic" film about the horrors of the holocaust. And it ends up looking like a mockery of the tragic events. The Academy was smokin' some serious crack in '97. ranna's rating:
 
80 7.6 7.5 Won: actress in a leading role - Judy Holliday
Should have won: Bette Davis from All About Eve A basic one-note-romantic-comedy-performance over one of Bette Davis' best roles? ranna's rating:
 
2248 6.6 7.2 Won: actress in a leading role - Gwyneth Paltrow
Should have won: Cate Blanchett from Elizabeth ranna's rating:
5457 7.7 8.5 Won: actor in a leading role - Russell Crowe
Should have won: Ed Harris from Pollock Talk about subtle delivery. "Are you not entertained? ARE YOU NOT ENTERTAINED?!?!" ranna's rating:
 
2210 6.7 7.2 Won: actress in a leading role - Julia Roberts
Should have won: Ellen Burstyn from Requiem for a Dream America's sweetheart proves that she can actually smile and frown. And all in one movie! So naturally she is awarded instead of Ellen Burstyn's tour-de-force perfonmance. ranna's rating:
1284 7.5 7.8 Won: actor in a leading role - Al Pacino
Should have won: Denzel Washington from Malcom X Look mom, it's a condolence Oscar! Ironically Denzel got his years later from the one note screaming-from-the-top-of-his-lungs performance in Training Day. ranna's rating:
523 7.4 7.7 Won: actor in a supporting role - Joel Grey
Should have won: Al Pacino or James Caan from The Godfather In case you haven't seen Cabaret - Joel Grey has about two lines in the movie. He plays the "Master of Ceremonies". That's right, no-one over bothered to name his sorry ass character. ranna's rating:
 
1066 7.5 7.8 Won: actor in a leading role - Rex Harrison
Should have won: Peter Sellers from Dr. Strangelove While Peter Sellers played three characters in one of the best films ever made, Rex Harrison starred in a musical. AND DIDN'T EVEN BOTHER TO SING. ranna's rating:
2314 7.1 7.7 Won: actress in a leading role - Helen Hunt
So, she basically portrays the same character as in Mad About You. Which also sucks. ranna's rating:
656 6.2 6.5 Won: actress in a supporting role - Jennifer Hudson
Should have won: Rinko Kikuchi from Babel 
1650 7.1 7.8 Won: actor in a supporting role - Tommy Lee Jones
Should have won: Ralph Fiennes from Schindler's List 
1596 6.7 7.2 Won: actress in a supporting role - Renée Zellweger
Something about Zellweger just pisses me off. ranna's rating:
1005 7.5 8.1 Won: actor in a leading role - Charlton Heston
I love you Charlton, but you have the emotional range of a brick wall. ranna's rating:
1704 7.5 7.6 Won: actor in a leading role - Sean Penn
Should have won: Mickey Rourke from The Wrestler Sean Penn is not a bad actor, but he has a tendency to overact. He's like a tasty, but an overly sweet dessert - best when served in small portions. But a leading role in a boring Hollywood drama? I'll pass. ranna's rating:
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Tilda Swinton's performance in Michael Clayton is just fine but it has nothing Oscar-worthy about it. Still, she picked up the award from best supporting role right under Cate Blanchett's nose, who was entitled to it due to her performance in I'm Not There.
This would mess up your neat top-15 though but give it a thought. :)
Not that he was bad, but Oscar.. Come on!
Oi! Apparently I must be on crack as well, how did I not see bob loblaw's comment before I wrote this...
I actually haven't seen The Blind Side, since it premiered in Finland just about a week ago. (And spending my well-earned cash on Sandra Bullock hasn't tempted me yet.) But I think that her win was very similar to Julia Roberts'. You know, America's sweetheart goes all serious.
You're right about Michael Clayton, it was a very mediocre performance. If this was a top 20, it would have surely made the cut! (As well as Cuba Gooding Jr. in Jerry Maguire.)
It would be great to hear your choices, though!