Top 10 Worst Best Picture Oscar-Winning Movies

#10 – “Driving Miss Daisy” (1989)

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Won Against: “Born on the Fourth of July,” “Dead Poets Society,” “Do the Right Thing” (not nominated). In 1989, movies like “Do the Right Thing,” “Glory” and “Miss Daisy” examined race issues, albeit in drastically different ways. But only the story of an elderly Jewish woman and her kindly black driver nabbed Oscar gold. We’re not suggesting “Driving Miss Daisy” is a bad film; but the Academy made the safe choice.

#9 – “Gandhi” (1982)

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Won Against: “Tootsie,” “E.T. the Extra-Terrestrial.” Sometimes movies stand the test of time. Sometimes they don’t. Unfortunately, this Best Picture winner falls into the latter category. While Sir Ben Kingsley’s performance and the film itself were lauded in their time, today it’s considered an overlong, corny snooze-fest. Y’know what movies do stand up? The one about a boy and an alien, and the one about a guy in drag. Go figure.

#8 – “Around the World in Eighty Days” (1956)

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Won Against: “Giant,” “The King and I,” “The Ten Commandments.” People scratched their noggins when this beat a category full of epic classics. Today, it’s even crazier to think that a hot-air balloon topped Moses, the King of Siam and James Dean. “Around the World” was basically a cash grab, with the big-name cameos, gimmicky storytelling and overall spectacle of the film making it one of the big prize’s weakest winners.

#7 – “Oliver!” (1968)

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Won Against: “Funny Girl,” “Romeo and Juliet,” “2001: A Space Odyssey” (not nominated). The Academy isn’t afraid to honor a good musical. Or even a bad one. “Oliver!” is somewhere in the middle, with Charles Dickens’ timeless tale being told through big-budget song-and-dance numbers. ’68 was a killer year for cinema, so to think that “Oliver!” brought home the gold while movies like this weren’t even nominated is a mindbender.

#6 – “How Green Was My Valley” (1941)

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Won Against: “The Maltese Falcon,” “Citizen Kane.” This film tackles the story of a poor mining town – not exactly life in the fast-lane. But this isn’t a case of the winning movie necessarily being bad; it just competed against cinematic landmarks. Did you even know “Citizen Kane” didn’t win the Oscar? To be honest, the only reason “Valley” is at all memorable is because it beat Orson Welles’ game-changing masterpiece.

#5 – “Dances with Wolves” (1990)

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Won Against: “Awakenings,” “Ghost, “GoodFellas.” The members of the Academy are suckers for historically-meaningful Civil War epics. And this one even has Native Americans! And subtitles! And a dashingly handsome actor-director who tries to save everyone! Y’can’t beat that. But Martin Scorsese’s “GoodFellas” should’ve. They must not like the f-word. Or, apparently, Scorsese, who was also snubbed for his 1980 tour-de-force “Raging Bull.” FYI, he finally won for “The Departed.”

#4 – “Chicago” (2002)

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Won Against: “The Lord of the Rings: The Two Towers,” “The Pianist.” We’ve already mentioned how Oscar voters feel about musicals. Pretty much everyone in this movie was nominated, with Catherine Zeta-Jones actually winning Best Supporting Actress. But some critics complained that when it was adapted to celluloid, “Chicago” lost what made it a great musical to begin with. But there was another movie that year with plenty of soul.

#3 – “The English Patient” (1996)

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Won Against: “Jerry Maguire,” “Fargo.” To put it bluntly: this movie was widely considered dull. But sometimes, you have to move past your boredom to truly appreciate an artistic and beautiful film. No, we’re kidding: no one wants to sit through an almost three-hours-long romance story set in the desert where the guy’s face is burnt off. You know what they do wanna see? Precisely. Or how ‘bout a nice wood-chipper?

#2 – “Shakespeare in Love” (1998)

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Won Against: “Saving Private Ryan.” In 1998, it was a triumph of the puff-piece: the Oscars are notoriously dead-set against comedies. But “Shakespeare” is also a period piece, which they love, and it had some fine acting and a breakthrough Gwyneth Paltrow performance. Maybe it was just time for a change? Regardless, after crafting one of the grittiest, most realistic and well-regarded WWII films ever, Steven Spielberg musta been pissed.

#1 – “Crash” (2005)

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Won Against: “Brokeback Mountain,” “Capote,” “Good Night, and Good Luck,” “Munich.” It’s a star-studded, carefully interwoven tale about race – but a preachy one at that. When Paul Haggis’ “Crash” was announced as winner, you could almost hear the collective gasp around Hollywood. There were simply so many deserving movies that year, and one in particular that examined another pressing social issue in a much more memorable and less patronizing way. Do you agree with our list? Which Best Picture winners were you most surprised about? For more top 10s about your favorite, and least favorite, flicks, be sure to subscribe to WatchMojo.com.