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10 Biggest Oscar Upsets in History

It’s a little strange, fundamentally, to argue and debate over the relative merits of artistic expression that are manifested at the Oscars. Really, how are we to say whether Rylance was better than Stallone, or whether DiCaprio was better than Cranston or Damon, or whether Spotlight was really the best movie of the year?

It’s one of the most subjective things we do on an annual basis. It’s not like it’s an MVP award in sports, where you can have some facts and figures to back things up; you can’t count up the number of touchdowns Alicia Vikander threw or the amount of home runs Brie Larson hit. You just have to go by your gut and your heart.

And that makes the Oscars fun to debate – and even more head-shakingly weird when they make a decision that goes against everyone’s gut and heart. So here’s our list of the ten most blatant Oscar screwups in history:

10. Geena Davis over Joan Cusack for Best Supporting Actor (1988)

Joan Cusack and Geena Davis

The Accidental Tourist is an inert Lawrence Kasdan drama from 1988 that seems to have been lost to the decade. Geena Davis somehow took home an award for her role in the snoozer as a dog-trainer who helps a grieving husband (William Hurt) recover. Contrast that to the wonderfully charismatic, hugely-haired Joan Cusack in Working Girl, who nearly steals the movie away from Melanie Griffith.

9. Jack Lemmon over the rest of the field for Best Actor (1973)

Jack Lemmon over Al Pacino, Robert Redford, Marlon Brando, and Jack Nicholson

Check out the field for Best Actor in 1973. Brando in Last Tango in Paris. Pacino in Serpico. Redford in The Sting. Nicholson in The Last Detail. And yet…the winner? Jack Lemmon for the strange, super-dated 70s tale Save the Tiger. Ever heard of it? Yeah, didn’t think so.

8. The English Patient over Fargo for Best Picture (1996)


The English Patient was a drawn-out snoozer of a historical epic now remembered chiefly for being the object of Elaine Benes’ scorn. How it beat the Coens’ beautifully unforgettable Fargo is mystifying.

7. The King’s Speech over The Social Network for Best Picture (2010)


The King’s Speech is a totally fine movie. Really, it is. It’s the best made-for-HBO movie ever made, with a (deservedly) Oscar-winning performance by Colin Firth at the heart of it. It checks off all of the Oscar-bait boxes: compelling British figure, fine production design, standout cast, better-than-competent direction. So it took home a boatload of gold on Oscar night.

That’s all well and good, but the best movie of that year was David Fincher and Aaron Sorkin’s marvelously realized The Social Network, which still feels bold and “of the moment” years after it came out. You can joke all you want about “that facebook movie” winning an Oscar, but it damn well should have.

6. Tim Robbins over Djimon Hounsou, Best Supporting Actor (2003)

Tim Robbins over Djimon Hounsou

Clint Eastwood’s movies collect Oscars like kids collect candy on Halloween night. That’s not to say they’ve always been deserving, though. Tim Robbins’ twitchy performance in Mystic River was one of the weakest links in the film, while Hounsou’s soulful and ferocious turn in In America was a heartfelt triumph.

5. Titanic over L.A. Confidential for Best Picture (1997)


Titanic works perfectly well as a spectacle feature, and it made a lot of money. Wonderful. James Cameron’s dialogue still clunks and clangs worse than the iceberg tearing into the damn ship. On the other hand, Curtis Hanson’s L.A. Confidential is a technicolor-brilliant film noir given a razor-sharp 1990s edge. It’s one of the great American movies, and it was the best picture of the year.  

4. Sandra Bullock over Gabourey Sidibe, Best Actress (2009)

Sandra Bullock over Gabourey Sidibe

The Blind Side was a competently crowd-pleasing biopic that hung a curveball right into Sandra Bullock’s wheelhouse – and she hit the hell out of it. But it’s a savoir stereotype role you’ve seen a thousand times before, and it just can’t compare to Sidibe’s raw and tortured performance in Precious. The fact that it was her first movie is still astonishing.

3. Crash over Brokeback Mountain for Best Picture (2005)


Crash is about as subtle as an asteroid strike. Brokeback Mountain is one of the most powerful, beautifully shot and intricately scripted love stories in movie history. Of course, that love story happened to feature two male cowboys…so, of course, Crash had to take home best picture. For shame.

2. Art Carney over Al Pacino for Best Actor (1974)

Art Carney over Al Pacion

It took an absurdly long time (until his showy, Hoo-ah laden performance in Scent of a Woman) for Al Pacino to win an Oscar, despite a stunning run of work in the 1970s. You could make an argument for several robberies in that decade, but none was more egregious than his loss in 1974 for The Godfather, Part II. Pacino’s Michael Corleone is one of the most vividly recognized characters in movie history – go on, try to get that quiet gut-punch of a final scene out of your head – and, compared to the sentimental hokum of Harry and Tonto, there shouldn’t have even been a contest. The great American crime saga against the tale of an old man trekking across America with a cat. Lord, the Oscars are strange.

1. Dances With Wolves over Goodfellas for Best Picture (1990)


The gold standard of all the best picture screw-ups over the years. Dances With Wolves isn’t a terrible movie – although it hasn’t aged well, as pointed out in this piece. A Best Picture nominee? Sure. But Goodfellas, as pretty much everyone agrees, is an absolutely perfect motion picture. Look back on the Oscar winners over the years, and this one sticks out like a big red thumb. Of course, along with that should have come a Best Director Oscar for Martin Scorsese, who provided the flair, style, and technical proficiency that made the picture so memorable – far more than Kevin Costner’s competently epic work ever did.

Are we missing some terrible upsets that you remember from the Oscars? Give them their fair shake in the comments below!

3 thoughts on “10 Biggest Oscar Upsets in History Leave a comment

  1. The worst Oscar upset: 1999 Best Picture = Shakespeare In Love. How that won over any of the other nominated pictures is beyond me. At the time, I recall really liking the movie, but that should not have translated into an Oscar over Saving Private Ryan, The Thin Red Line, Life is Beautiful, or Elizabeth. Any of these movies would have been a better choice. That Shakespeare in Love has not held up over the years does not help it any. The only reason it won, I think, is because of the juggernaut of Harvey Weinstein (Miramax at the time) and his incredible Oscar campaigns.

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