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The 10 Biggest Oscar Upsets of the Last 10 Years

Upset that there were no Oscar upsets this year? Here are the 10 biggest shockers in recent memory.

The 10 Biggest Oscar Upsets of the Last 10 Years

As you might have noticed from our Oscar predictions, there really weren’t any upsets at the Academy Awards this year. Pity. Those rare moments when the obvious winner doesn’t take home the Oscar are some of the most dramatic moments in the show’s history. Of course, that’s partly what makes them so rare.

So as we bemoan the 83rd Annual Academy Awards for going by the book, we take this opportunity to remember the most recent, shocking upsets of the last ten years. Maybe next year Megan Fox will trounce Meryl Streep for Best Actress or something, but until then let’s look back and try to remember the last ten times when the Oscars went totally off-script. 

10. (TIE) – Sean Penn wins Best Actor over Bill Murray (2004); Sean Penn wins Best Actor over Mickey Rourke (2009)


Not so much an upset, per se, but twice now Sean Penn has won for Best Actor, and twice he’s won over a competitor who by all rights should have won for their story alone. Both Bill Murray in Lost in Translation and Mickey Rourke for The Wrestler were considered prime contenders for Best Actor in 2004 and 2009 respectively. The veteran funnyman had never been nominated before despite heavy Oscar buzz for Rushmore, and Mickey Rourke had made a celebrated return to form after years of wallowing in obscurity. Both performances made headlines and were incredible and award-worthy… but both were trounced come Oscar time by Penn, a former Oscar pariah himself, for his starring roles in Mystic River and Milk. Nobody’s denying that Penn deserved the awards (well, maybe not for Mystic River), but it still seemed like Bill Murray and Mickey Rourke’s years. Neither has been nominated before or since.

 

9. Departures wins Best Foreign Film over Everything Else That Was Nominated (2009)


The Best Foreign Language Film award has always been a bit of a crapshoot (see #3 on our list for the most shocking example in recent memory), but seriously, what the heck is Departures? The still unknown and underseen Japanese film about an unemployed cellist who takes a bizarre gig preparing the deceased for funerals shocked the industry (if not necessarily the viewers, who don’t pay much attention to the category) when it won out over better publicized films like the German terrorist drama The Baader-Meinhoff Complex, the feel-good underdog music teacher Oscar bait The Class, the acclaimed crime thriller Revanche and the topical quasi-animated Israeli war picture Waltz with Bashir to take home the prize. It may not have been the award everyone cared about, but it was one of the few times in history when the least likely nominee ever took home the Oscar in any category.

 

8. Tilda Swinton wins Best Supporting Actress over Amy Ryan (2008)


Ben Affleck’s directorial debut Gone Baby Gone doesn’t get enough credit for being one of the most challenging and morally complex American dramas of the last decade, but Amy Ryan’s performance as the mother of a kidnapped child was all anyone could talk about for about six months. So it was a surprise to see Tilda Swinton take home the Academy Award for Best Supporting Actress instead for Michael Clayton. Swinton’s daring portrayal of a decent person watching herself transform into a corrupt corporate villain certainly earned her the gold, but until the actual award was announced it was Ryan whose role seemed destined for Oscar immortality as a terrible mother who perhaps genuinely loved her son. Ryan hasn’t been nominated before or since, but her career is still going strong with regular roles on the TV series The Office and In Treatment.

 

7. The Lord of the Rings: The Return of the King wins Best Original Song over The Triplets of Belleville (2004)


After two years of being snubbed for Best Picture The Lord of the Rings returned with a vengeance, sweeping the 2004 Academy Awards in all eleven (!) categories in which The Return of the King was nominated. Most of us were surprised it didn’t only win ten, since it was up against one of the best original songs of the decade in The Triplets of Belleville. The sedate, dramatic tune “Into the West” took home the Oscar for Best Original Song, riding the wave of LOTR’s popularity while the obvious frontrunner “Belleville Rendez-Vous” went home empty-handed. The nouveau swing-dancing classic lives on in the iPods of hipsters and film lovers alike. “Into the West” hasn’t been heard (from, or at all) since the Oscar ceremony. 

 

6. Crash wins Best Picture over Brokeback Mountain, or possibly Ang Lee wins Best Director over Paul Haggis (2006)


2006 was a real horse race for Best Picture, with sentimental racist cliché-fest Crash competing against the homosexual cowboy romance Brokeback Mountain for the big prize. (Their ‘competition’ – Capote, Munich and Good Night and Good Luck – was anything but.) Depending on who you talk to, Ang Lee’s win for Best Director was a shocking upset over Paul Haggis, or Crash’s win for Best Picture was a shocking upset over Brokeback Mountain. There wasn’t much overlap in the fan base, so everyone went home disappointed that their favorite film didn’t take home both honors, rather than everyone going home happy that they were divided evenly amongst the two prime contenders. Two-time Academy Award-winner Paul Haggis hasn’t been nominated in the category since, although he did garner a Best Adapted Screenplay nomination for Letters from Iwo Jima in 2007. Neither of Ang Lee’s subsequent features, Taking Woodstock and Lust, Caution, have been nominated for a single Academy Award… let alone Best Picture.

 

5. Alan Arkin wins Best Supporting Actor over Eddie Murphy (2007)

 

Despite a surprising up swell of support for his performance in The Nutty Professor, Eddie Murphy was never considered much of an Oscar contender until his performance as James ‘Thunder’ Early in Bill Condon’s Dreamgirls. Everyone believed that the Academy would give the comedy legend his due… until Norbit came out during the voting cycle. The painfully unfunny fat cross-dressing comedy dragged Murphy’s newly good name in the mud at exactly the wrong time, and many believed it cost him the Oscar which had been all but set aside for him by the Academy. Another former also-ran, Alan Arkin, surprised audiences – and, famously, Murphy himself – when he won Best Supporting Actor instead for his role as the hilariously heroin addicted grandfather in Little Miss Sunshine. Arkin had been nominated twice before, back in the 1960’s (!), but had never won before. Murphy hasn’t been nominated since, and despite a brief boost in notoriety from Dreamgirls has yet to star in a viable Oscar candidate again, focusing instead on family comedies like Imagine That, Meet Dave, and his recurring role as the Donkey in Shrek.

 

4. Adrien Brody wins Best Actor over Daniel Day-Lewis (2003)


Daniel Day-Lewis blasted onto the screen in Martin Scorsese’s Gangs of New York, embodying 19th Century gangster Bill The Butcher with a brash bravado that stirred audiences even while the rest of the film left them cold. But although his instantly iconic performance made him the odds-on favorite for Best Actor in 2003 he went home empty-handed. Adrien Brody instead took home the Oscar for his subdued but powerful performance in The Pianist, making him the youngest actor to earn the Academy Award for Best Actor at the tender age of 29 (!). He famously planted an enormous smooch on Halle Berry as he took the stage, but hasn’t been nominated since. Daniel Day-Lewis’s loss would be short-lived: he took home an even more richly deserved Academy Award for There Will Be Blood in 2008.

 

3. The Lives of Others wins Best Foreign Language Film over Pan’s Labyrinth (2007)


Guillermo Del Toro’s critically acclaimed masterpiece Pan’s Labyrinth was snubbed in the Best Picture category, but that seemed perfectly all right. It was a shoe-in for Best Foreign Language Film, right? Apparently not. Despite the film’s notoriety and three other Oscar wins for Best Cinematography, Art Direction and Makeup, Pan’s Labyrinth lost the big award to Florian Henckel von Donnersmarck’s quietly thrilling Nazi fest The Lives of Others. A great film, but a shocking upset against a movie many considered one of the best of the year… if not the decade. Florian Henckel von Donnersmarck’s follow-up to The Lives of Others was the critically panned flop The Tourist – which we actually really liked, at the risk of being unpopular – which eked out a couple of Golden Globe nominations but was snubbed by the Academy. Del Toro hasn’t been nominated for an Oscar since, instead directing Hellboy II: The Golden Army and attaching himself to countless projects including The Hobbit (a project he eventually left after production was pushed back), a remake of Frankenstein and his upcoming adaptation of H.P. Lovecraft’s At the Mountains of Madness.

 

2. Roman Polanski wins Best Director over Martin Scorsese and Rob Marshall (2003)


The 2003 Best Picture race was considered a dead heat between Rob Marshall’s Chicago and Martin Scorsese’s Gangs of New York. The toe-tapping musical won the big award, but many believed that Scorsese’s history of Oscar snubs left him open to winning Best Director if Rob Marshall didn’t pull it off. Neither of the frontrunners took home the Best Director prize, however… Instead, Roman Polanski took home the Academy Award for The Pianist in one of the most genuinely Oscar shocking upsets of the last decade. Polanski’s legal woes made him an unlikely nominee, let alone winner, but the overwhelming quality of The Pianist led the Academy to award him anyway, even if he was unable to accept the Oscar for risk of arrest on six criminal charges, including unlawful sexual intercourse with a minor.

 

1. Jim Broadbent wins Best Supporting Actor over Sir Ben Kingsley and Sir Ian McKellan (2002)


But as shocking as Roman Polanski’s win was, he was still acclaimed director Roman Polanski and The Pianist was still a well-known, critically lauded drama. In contrast, Jim Broadbent’s Academy Award for Best Supporting Actor in 2002 came out of nowhere. The award was heavily favored to go to either Sir Ian McKellan for The Lord of the Rings: The Fellowship of the Ring or Sir Ben Kingsley’s explosive turn in Sexy Beast. Heck, Ethan Hawke had a better chance of winning for Training Day. Instead they all went home empty handed and Broadbent won the Oscar for his inspiring performance in the tiny British Alzheimer’s drama Iris, leading viewers around the world to exclaim in unison: “What the f*** is Iris?” It’s actually a very good movie and a very deserving performance, but it was easily the most surprising Oscar upset of the last ten years. Maybe Broadbent’s performance in Moulin Rouge that same year bolstered his chances. Or maybe he was just that good. He certainly has the Oscar to prove it.