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The Envelope, Please: Eleven Famous Oscar Upsets

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This month, millions of people around the country will watch Hollywood royalty and newcomers gather and present each other with awards. I don’t know about you, but I can’t wait! The Oscars is like my Super Bowl; I love watching the pregame coverage (read: red-carpet fashion shows) and finding underdogs to root for. And just as football fans cry out in agony when their favorite teams are defeated, my heart breaks a little when the movie or actor I want to win goes home empty-handed. 


Given the backlash over some victories in Oscar history, I’m definitely not alone in my occasional outrage at members of the Academy of Motion Picture Arts and Sciences. When they get it right—as with Sean Penn’s and Kate Winslet’s wins in 2009, the victory seems especially sweet. But when the Oscar’s handed to someone audiences deem more undeserving than underdog, calling it an upset is putting it mildly. 


1. Crash wins Best Picture, 2006
Brokeback Mountain went into the ’06 Oscars as the critics’ darling, even earning a Best Director award for Ang Lee. But at the end of the night, the Best Picture title went to Crash, shocking Hollywood and sparking allegations of homophobia among voters. 


2. Grace Kelly wins Best Actress, 1954
Judy Garland returned to the screen after years of drug and financial problems with A Star Is Born. It was a critically acclaimed comeback that almost guaranteed her victory on Oscar night … except that Grace Kelly won instead for The Country Girl. Garland fans still haven’t accepted the defeat. 


3. Gwyneth Paltrow wins Best Actress, 1999
Paltrow had already won a Golden Globe for Best Actress, and Shakespeare in Love boasted a whopping thirteen Oscar nominations going into the race, but audiences were still surprised by her win. She was up against Cate Blanchett, whose portrayal of the virgin queen in Elizabeth drew widespread adulation. 


4. Adrien Brody wins Best Actor, 2002
There was already controversy surrounding The Pianist because its director, Roman Polanski, had fled the country to escape prosecution for statutory rape. So when the film’s leading man, a Hollywood novice, beat out heavyweights like Jack Nicholson (the favored win for About Schmidt) and Daniel Day-Lewis, people were surprised, to say the least. Brody’s big smooch with award presenter Halle Berry post-victory didn’t help matters, either. 


5. Shakespeare in Love wins Best Picture, 1999
Again, it claimed more nominations than any movie in history at the time and had star power—Joseph Fiennes, Judi Dench, etc.—but few would argue that it was a better movie than the groundbreaking and visually stunning Saving Private Ryan. Shakespeare in Love may have been a great love story, but it didn’t hold a candle to Spielberg’s masterpiece. 


6. Marissa Tomei wins Best Supporting Actress, 1992
The long-running rumor is that the presenter, Jack Palance, announced the wrong winner and that the Academy was too embarrassed to fix the error. But while the industry was in denial that the young actress Tomei could beat out veterans like Vanessa Redgrave and Miranda Richardson, that was indeed the case. 


7. Sean Penn wins Best Actor, 2009
Even though Penn was my top pick for his inspiring, heartfelt turn in Milk, many expected Mickey Rourke’s comeback performance in The Wrestler to be the standout favorite. But, as Garland did on her disappointing night in 1954, Rourke went home empty-handed. He did win a Golden Globe, though. 


8. Juliette Binoche wins Best Supporting Actress, 1996
After many close calls with Oscar victory but without a single trophy to her name, Lauren Bacall was going to finally have her year in 1996. Her role in The Mirror Has Two Faces earned almost immediate Oscar buzz. Even Binoche, who claimed the win for The English Patient, was sure her competition would win and said so in her acceptance speech. But Bacall finally got her man—she was awarded an honorary Oscar in 2009. 


9. How Green Was My Valley wins Best Picture, 1941
The American Film Institute may have ranked Citizen Kane the number one movie of all time in 2007, but the Academy didn’t feel the same way back in ’41, when it gave the Oscar to How Green Was My Valley, a John Ford–directed drama. It also beat out The Maltese Falcon and earned John Ford a Best Director award. 


10. Cher wins Best Actress, 1988
Cher’s known more for her plastic surgery and cheesy music these days, but back in the 1980s, she held her own against venerable actors like Nicholas Cage and Olympia Dukakis in Moonstruck. What’s more, she outshined them! Most people might not have expected her to beat out Glenn Close and Meryl Streep, but that she did. She also claims the title of wearing one of the most revealing, scandalous dresses in awards-show history to boot. 


11. Cuba Gooding Jr. wins Best Supporting Actor, 1996
Edward Norton nabbed a Golden Globe for his disturbing, intense portrayal of Aaron Stampler in Primal Fear. That wasn’t enough to seal the deal for him on Oscar night, though—Gooding won for his role in Jerry Maguire instead. Industry insiders thought for sure it was Norton’s time to shine, but Gooding grabbed the prize and offered up one of the best acceptance speeches, too. He even did a back flip onstage! 


Who knows what’ll happen come Oscar night this year? If past years are any indication, there’s sure to be some laughter, tears, astounding victories, and heartbreaking defeats. And like any hardcore fan, I’ll be watching—and enjoying—every minute of it.

Updated January 24, 2011

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