The Top 10 Biggest Oscar Upsets

With only days until this year’s telecast, all fans – from moviegoers ourselves to industry insiders – have begun the ritual of predicting the winners of the greatest award show of the year. And while it’s very satisfying to see one’s selections called up on the stage as winners, what makes the event most memorable is when expectations are completely overthrown by reality. History has seen its share of incredible Oscar upsets. Here are the top ten.

No. 10 – Three 6 Mafia Beats Dolly Parton (2006)

If this year’s telecast will teach us anything, it’s that the Oscars is a very, very white affair. (“Selma” who?) But throughout history, there have been a person of color or two to take home gold statues of their own. In 2006, there were at least three, when Three 6 Mafia pulled off one phat surprise when their rap “It’s Hard Out There for a Pimp” b-slapped Dolly Parton’s trans-friendly “Travelin’ Thru” as Best Original Song. The musical trio, who in true hip hop style all opted out of black tie, were a welcome sight on the Dolby Theatre stage, as was Parton in her seat. Her reaction to their win showed as much excitement as if the envelope had contained her own name. (Photo credit: Michael Caulfield/WireImage)

No. 9 – Marisa Tomei Wins Best Supporting Actress (1993)

Very rarely do pure comedies lead their performers to Oscar gold. And Oscar audiences have rarely been as surprised as they were to see newcomer Marissa Tomei beat four Hollywood heavyweights for a Best Supporting Actress win. As far as the Academy was concerned, Vanessa Redgrave, Miranda Richardson, Judy Davis, and Joan Plowright were no match for Tomei’s scene-stealing turn in “My Cousin Vinny.” (Photo credit: Barry King/Liaison)

No. 8 – “Rocky” Wins Best Picture (1977)

Rocky Balboa was a driven underdog who conquered a well-established champion. At that year’s Oscars, a parallel could be drawn to the film itself. “All The President’s Men,” “Network,” and “Taxi Driver,” all contenders for filmmaking’s greatest examples ever, fell to the scrappy feel-good boxing hit. “Rocky” snatched the Best Picture award from them all with the shock of a consciousness-erasing left hook. (Photo credit: Ron Galella/WireImage)

No. 7 – Adrien Brody Wins Best Actor (2003)

Going into the Oscar ring against titans Jack Nicholson, Michael Caine, Nicholas Cage and Daniel Day-Lewis would seem like an insurmountable task. But 29-year-old Adrien Brody surmounted and snatched the Best Actor prize from all four for his heartbreaking performance in “The Pianist.” Maybe no one was more surprised by this than Brody himself – who became the youngest man to win that award – except for presenter Halle Berry, whom the actor literally swept off her feet to plant a big, celebratory kiss upon her in what became one of Oscars greatest moments ever. (Photo credit: Frank Micelotta/Getty Images)

No. 6 – “How Green Was My Valley” Beats “Citizen Kane” for Best Picture (1942)

Though by no means as horrifying as the atrocities then playing out around the globe, in 1942 the Biltmore Hotel hosted what many film historians might conclude an act of war. John Ford’s formidable family saga “How Green Was My Valley” defeated what is now considered by most as the greatest film ever made, “Citizen Kane,” in their quests for Best Picture. Amazingly at the time, “Kane” was poorly received and disregarded, particularly by William Randolph Hearst, the media baron upon whom director/star Orson Welles based the titular character and whose newspapers suspiciously denied any printed mention of the film that would one day be known as a masterpiece. (Photo credit – Hulton Archive/Getty Images)

No. 5 – Gwyneth Paltrow Beats Cate Blanchett for Best Actress (1999)

Maybe she began drawing the ire of her haters here. Everyone expected Cate Blanchett’s royal performance in “Elizabeth” to earn her Best Actress gold. But with the Weinstein’s aggressive For Your Consideration campaign, “Shakespeare in Love” dominated the night and made a 26-year-old Paltrow the winner. Vanquishing a beloved queen – now that’s Shakespearean. (Photo credit: TIMOTHY A. CLARY/AFP/Getty Images)

No. 4 – “Dances With Wolves” Beats “Goodfellas” for Best Picture (1991)

“Taxi Driver’s” loss to “Rocky” was the beginning of a long tradition of unimaginable Academy Award defeats for Martin Scorcese. “Raging Bull,” “Gangs of New York” and “The Aviator” all earned the legendary filmmaker nominations for Best Director and he lost them all. But since 1976, perhaps no snub was as great as his loss to Kevin Costner’s “Dances With Wolves.” “Goodfellas” has attained the status of a true cinematic achievement, one of the ’90s greatest for sure, if not all time. But audiences were dazzled by “Dances” epic story and newbie director Costner’s sweeping style. And Oscar rewarded the beloved actor with one trip to the Shrine Auditorium’s stage after the next, while Scorsese remained stuck to his seat. (Photo credit: Ron Galella/WireImage)

No. 3 – Roberto Benigni Beats Tom Hanks for Best Actor (1999)

Tom Hanks was well on his way to joining a very select group of Oscar winners who’ve won three of the award’s top acting statues for his role as the company commander in “Saving Private Ryan.” But he got stopped in his tracks by one boisterous Italian. Roberto Benigni had a WWII pic of his own, “Life is Beautiful,” which chose gloom and glee over “Ryan’s” gloom and doom. His multiple wins that night delighted the audience as he literally bounced about and climbed on Dorothy Chandler Pavilion chairs in celebration. Maybe security (or Hanks) were truly displeased. As far as we know, Roberto Benigni has not been seen since. (Photo credit: TIMOTHY A. CLARY/AFP/Getty Images)

No. 2 – “Crash” Beats “Brokeback Mountain” for Best Picture (2006)

Racist Los Angelenos and gay cowboys duked it out for Best Picture at the 78th Annual Academy Awards, and while the cowboys were heavily favored, it was the racists who came out on top. “Brokeback Mountain” was anointed by critics as a true achievement in filmmaking with Heath Ledger and Jake Gyllenhaal’s performances as the star-crossed lovers breaking the sexual barriers a mainstream Hollywood had quietly but forcefully instituted since movie cameras first started to roll. But “Crash” was a glossy message movie with a star-studded cast and once awards season started, began to rack them up like a young driver’s moving violation citations. The Oscars were no different, and “Crash” took home the top statue, leaving shocked audiences with unexpected cases of whiplash. (Photo credit: AFP PHOTO/Timothy A. CLARY/Getty Images)

No. 1 – “Shakespeare in Love” Beats “Saving Private Ryan” for Best Picture

“Saving Private Ryan” was expected to storm the Oscars like a beach in Normandy. And it’s piece de resistance was to have been the Best Picture statue. But Judi Dench’s win for “Shakespeare in Love” ignited that film’s major category sweep and ultimately shot down Steven Speilberg’s WWII epic to nab the top prize. Academy voters had a clear choice between love and war for its most prestigious award, and surprisingly, but in true Hollywood fashion perhaps, chose the former. (Photo credit: HECTOR MATA/AFP/Getty Images)

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