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How Green Was My Valley wins Best Picture (1942) To this very day, cineastes belabor and bemoan the fact that John Ford’s genteel portrait of life in a Welsh coal-mining town was named Best Picture over Orson Welles’ stirring fictional biography of a ruthless publishing magnate (who every one pretty much knew was William Randolph Hearst). What they usually forget to point out is that same year Valley also beat out such film classics as The Maltese Falcon, Sergeant York and Alfred Hitchcock’s Suspicion. Any one would have made more sense than the film that took home the trophy.

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Marisa Tomei wins Best Supporting Actress (1993) Before My Cousin Vinny, Marisa Tomei was best known for her stint on the daytime soap As The World Turns and walk-on support roles in low-budget films like The Toxic Avenger. On this particular Oscar night, however, her portrayal of a brassy Bronx babe earned her filmdom’s highest honour, even up against such heady competition as Vanessa Redgrave in Howard’s End and Miranda Richardson in Damage. The public disbelief in Tomei’s win eventually morphed into a rumour that Oscar-presenter Jack Palance had actually read the wrong name, but they gave the award to Tomei anyway. Not true.

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Gwyneth Paltrow wins Best Actress (1999) Really? Gwyneth Paltrow? Sure, Shakespeare in Love had a boatload of nominations going into the Oscars, but nobody really believed Paltrow had a chance opposite Meryl Streep (One True Thing) and Cate Blanchett (Elizabeth). By appearances even Paltrow didn’t believe she had a chance, as evidenced in her rambling, tear-soaked acceptance speech. Next stop: Chris Martin!

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Shakespeare in Love beats Saving Private Ryan for Best Picture (1999) But the bigger surprise came later that same night. A breakout film for Steven Spielberg’s fledgling DreamWorks studio, Saving Private Ryan was a gutsy wartime drama with big Hollywood stars (Tom Hanks, Matt Damon, et al) and more than a half-billion earned at the box-office. By comparison, Shakespeare in Love was a frilly period piece, but producer and Miramax head Harvey Weinstein had shrewdly mounted a relentless publicity campaign leading up to the Oscars (including free screenings and dinners at the retirement homes of some Academy voters) that turned the tide in its favour. Spielberg skipped the Oscars after-party that year.

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Denzel Washington wins Best Actor (2002) It’s not often that you see the grin wiped off Will Smith’s face, but it vanished the moment Denzel Washington’s name was announced as Best Actor. Smith had bulked up and prepared for a year to play Muhammad Ali in the biopic Ali and was picked by Vegas touts as the man to beat; all Washington had to do fin Training Day was put on a leather jacket and play it cool. Adding to the upset quotient was the fact Washington beat Russell Crowe as the clinically-depressed math genius in A Beautiful Mind and Sean Penn for playing a mentally-challenged adult in I Am Sam, both typical chew-up-the-scenery type portrayals. Not on Denzel’s watch, baby.

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Three Six Mafia Wins Best Original Song (2005) Most people in Hollywood were surprised when the song It’s Hard Out Here for a Pimp (from the film Hustle & Flow) by the rap trio Three 6 Mafia was nominated for Best Original Song; when the song actually won the award, you could actually see the shocked look on many people’s faces. Except possibly for Dolly Parton, whose song Travelin’ Thru (from the film TransAmerica) was also up for the same award. Dolly’s face hasn’t moved in years.

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Kathryn Bigelow wins Best Director (2010) Some upsets are simply too sweet for words. Besides being the first woman to ever win the Best Director award, Bigelow and her low-budget ($7-million US) anti-war treatise The Hurt Locker also beat out her ex-husband James Cameron, whose mega-budget epic Avatar was considered the odds-on favourite. Having the statuette presented to her by Barbra Streisand–one of very few woman bold enough to direct back in the seventies and eighties–made the victory that much sweeter for Bigelow, back in contention this year for Zero Dark Thirty.

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