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Oscar's 13 Biggest Mistakes

Crash
Lionsgate

For every winner who leaps up to thank the Academy, at least four nominees stay behind -- and with them, countless audience members wondering why their favorites failed to snag the big award. But there are times when everyone -- maybe even the winner -- believes the wrong name was read and the Oscar should have gone to... someone else.

We've picked 13 unlucky times the Academy made a huge, irreversible mistake, whether out of misguided loyalty to an actor-turned-director, fear of bestowing the Oscar to a violent or controversial film, or for no discernible reason at all (in no particular order).

'Ordinary People' Over 'Raging Bull' (Best Picture, 1980)

Ordinary People
Paramount

Robert Redford's family drama beat Martin Scorsese's sweeping boxing epic in a decision that still leaves Oscar buffs shaking their heads in confusion. "Ordinary People" was a fine study of familial dysfunction, but its popularity arose largely from Redford in his directorial debut, and Mary Tyler Moore playing against type as an unfeeling mother. Not only did the film win, but Hollywood's golden boy also won the Best Director award (for his first film!), leaving the Manhattan maverick empty-handed for the first of five times. Scorsese wouldn’t win for another 26 years, with "The Departed" in 2006.

'Crash' Over 'Brokeback Mountain' (Best Picture, 2004)

Rarely does a film win Best Director and Best Screenplay but not Best Picture. We can only imagine Ang Lee's heartbreak after every film critic, Oscar pundit, and Las Vegas bookie predicted his tender cowboy love story would win the top prize... only to lose to an overrated directorial debut from screenwriter Paul Haggis. Some blamed "Brokeback"'s loss to homophobia, but more likely "Crash" benefited from its authenticity as an L.A. story and Haggis' popularity as the previous year’s screenwriting winner for "Million Dollar Baby."

Al Pacino Over Denzel Washington (Best Actor, 1992)

The prize went to Pacino, for "hoo-ya”ing his way through an(other) over-the-top performance as a lonely blind man in "Scent of a Woman." The Academy was clearly granting a much-overdue statuette to Pacino, who was already 0-for-7 by that year. Perhaps they also thought that Washington, who already had a Best Supporting Oscar for "Glory," would go on to more award-worthy roles, or that his uncanny titular portrayal in Spike Lee's “Malcolm X” was too incendiary. Washington, like Pacino, eventually won a Best Actor ("Training Day"), but not, like Pacino, for his career-defining role.

'How Green Was My Valley' Over 'Citizen Kane' (Best Picture, 1941)

Film buffs revere the second as one of the greatest movies ever made; the first won Best Picture in 1941. At the time, though, the Academy loved John Ford, the director of the dramatic literary adaptation "How Green Was My Valley" (he went on to win four out of five directing awards) and all but sneered at the fiercely independent Orson Welles. That disdain made Welles’s singular masterpiece (the AFI has ranked it as the Greatest Movie of All Time, twice) one of the biggest losers in Oscar history -- it won just a single Oscar (Best Original Screenplay) from its nine nominations.

Tommy Lee Jones Over Ralph Fiennes (Best Supporting Actor, 1993)

Another example, harshly criticized, of voting for the career over the performance. Sure, we remember Jones' role as the determined Deputy U.S. Marshal in "The Fugitive," but we remember nearly every line, every gesture, and every squint of the eye Fiennes delivered as the sadistic Nazi officer Amon Goeth in "Schindler's List." Fiennes deserved the award just for his chilling "Today is history" monologue alone.

'Shakespeare in Love' Over 'Saving Private Ryan' (Best Picture, 1998)

Shakespeare in Love
Miramax

Miramax's ultimate upset has been attributed more to executive producer Harvey Weinstein's über-aggressive award machinations (remember "Chocolat"?) than the overall worth of John Madden's romantic period piece. It obviously stung (and stunned) the momentarily confused "Saving Private Ryan" director-producer Steven Spielberg and star Tom Hanks, since everyone expected the WWII drama's triumph. Twelve years later, we're still wondering what the sweet costume drama did -- as Hanks' Captain so memorably told Private Ryan -- to "earn this" award.

Judy Holliday Over Bette Davis AND Gloria Swanson (Best Actress, 1950)

To be fair, Judy Holliday's comedic performance as showgirl arm-candy in "Born Yesterday," had snob appeal (she had originated the role on Broadway), but fans are still mystified how she beat Bette Davis’s iconic performance in "All About Eve" or even Gloria Swanson's "I'm ready for my close-up" role in "Sunset Blvd." One possible explanation: evil, or should we say Eve-ish Anne Baxter, who demanded to compete as a Best Actress contender for "All About Eve," splitting the vote that should've cemented the award for Davis.

Gwyneth Paltrow Over Cate Blanchett (Best Actress, 1998)

Like the Best Picture award, Harvey Weinstein's marketing prowess probably gave Paltrow her win for playing William Shakespeare's beautiful muse. The studio chief even called Paltrow the "Muse of Miramax" during his acceptance speech, making it clear poor Cate Blanchett never really had a chance, even though she blew critics and audiences away as the young Queen "Elizabeth." Since then, Blanchett has shown the Academy its error, with four more nominations (including two the same year!) and one win, compared to Paltrow's none.

'Dances With Wolves' Over 'Goodfellas' (Best Picture, 1990)

Oscar voters love a good epic, but apparently not ones about New York gangsters. Instead, the Academy once again celebrated the successful transition of an actor-turned-director by completely shutting out Marty Scorsese (first in favor of Robert Redford then Kevin Costner 10 years later). Costner's tale of a Civil War officer who joins a Sioux clan has plenty of moving moments, but it’s since been criticized as being condescending to Native Americans. Nobody, on the other hand, disputes the brilliance of "Goodfellas," which Roger Ebert has praised by saying, "No finer film has ever been made about organized crime - not even 'The Godfather.'"

'Forrest Gump' Over 'Pulp Fiction' (Best Picture, 1994)

Forrest Gump
Paramount

As Forrest's mama said, "stupid is as stupid does," and looking back, the Academy's decision to pass over "Pulp Fiction" for Best Picture was predictable, perhaps even understandable, but still stupid. The voters -- especially older voters -- weren't keen on the ultra-violent, nonlinear musings on life, death, and anal rape in the criminal underworld of greater Los Angeles, but they had to know Quentin Tarantino's masterpiece was something they'd never seen before, so they threw him the consolation prize of Best Original Screenplay.

Mira Sorvino Over Kate Winslet (Best Supporting Actress, 1995)

It's not all that surprising, given the unpredictable nature of the Supporting Actress award, but it's in retrospect, as it was at the time, hard to understand why Sorvino's bubbly prostitute in Woody Allen's "Mighty Aphrodite" beat out Winslet's first award-worthy performance in Ang Lee's "Sense and Sensibility." Even if you don't count what each actress went on to accomplish (Winslet became the youngest actress ever to garner five Oscar nods before finally winning for her sixth; Sorvino ... didn't), it's a puzzling selection.

Robert Donat Over Clark Gable (Best Actor, 1939)

Frankly my dear, we can't believe Gable's unforgettable role as the dashing Rhett Buttler in "Gone With the Wind" went unrecognized. Seventy years later, we’re still quoting Gable, while we’re googling who Robert Donat was, how his performance could have outshone Gable’s, and what "Goodbye Mr. Chips" was about (FYI, the titular octogenarian recalls his long career as a boarding-school professor). We'll grant that in 1939, Donat had more screen time than Gable, but seven decades later, Rhett Butler is an icon, and Mr. Chips is Oscar trivia.

Sean Penn Over Mickey Rourke (Best Actor, 2008)

You know how actors are supposed to remain stoic in the face of defeat? Mickey Rourke didn’t get the memo. He looked crushed after his multiple-award-winning comeback as the aged and lonely "The Wrestler" failed to earn him Hollywood's top prize. Penn, who had won five years earlier for "Mystic River," edged him out in the end for playing the beloved late Mayor of the Castro, Harvey "Milk." Rourke, a revelation in Darren Aronofsky's intimate drama, was probably unfairly docked points for his many years of self-destructive tabloid fodder.

Originally published Feb. 24, 2011.

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