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10 worst Oscar winners ever, ranked

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Ahead of this year’s Academy Awards, we’re looking back at the ten worst Oscar winners that were named Best Picture of the year.
When a film is named the Best Picture of the year at the Oscars, it comes with the expectation that the flick in question is among the all-time greats. For the most part, this has been true. Few people could convincingly argue that movies like Casablanca, On the Waterfront, Lawrence of Arabia, The Godfather, The Godfather Part II, Schindler’s List, and No Country for Old Men failed to live up to that billing.
Regardless, there are a handful of movies that, in hindsight, simply didn’t deserve to go home with cinema’s top prize. And those are the films that we’re putting on blast in our list of the ten worst Oscar winners ever. It’s too soon to say whether the Academy will make the right choice on Sunday, March 10. But for these movies, the verdict is in.10. Shakespeare In Love (1998)
Shakespeare In Love is actually a pretty good romantic comedy that went a long way towards making Gwyneth Paltrow a star. Joseph Fiennes stars as William Shakespeare, and he does indeed fall in love with the fair Viola de Lesseps (Paltrow) in a way that mirrors many of his most famous plays. Judi Dench has a small supporting role as Queen Elizabeth I, which won her an Oscar for Best Supporting Actress.
Shakespeare In Love ended up on this list because it has a bad reputation attached to its Best Picture win. Disgraced film producer Harvey Weinstein pulled out all the stops while running the campaign to give this film the Oscar, which was unusual for the time. Would Shakespeare In Love have won without Weinstein’s politicking? We’ll never know for sure, but we suspect that Steven Spielberg’s Saving Private Ryan would have won under ordinary circumstances. And perhaps it should have.
Watch Shakespeare In Love on Max.9. How Green Was My Valley (1941)
How Green Was My Valley‘s claim to fame is that it triumphed over The Maltese Falcon and Citizen Kane, the latter of which is widely regarded as one of the best movies ever made. On its own terms, How Green Was My Valley is an okay film that gave Planet of the Apes‘ Roddy McDowall one of the primary roles as Huw Morgan, the youngest son of a mining family that faces severe hardships in the 19th century.
This movie was directed by John Ford, the only man ever to win Best Director four times at the Oscars. Ironically, Ford’s The Grapes of Wrath was nominated for the same award a year earlier than How Green Was My Valley, and the former is the film that has withstood the test of time. Compared to that movie, How Green Was My Valley is very forgettable.
Rent or buy How Green Was My Valley on Prime Video.8. Around the World in 80 Days (1956)
Around the World in 80 Days may be one of the most famous examples of the triumph of spectacle over substance. Director Michael Anderson adapted Jules Verne’s novel of the same name, which follows the adventures of Phileas Fogg (David Niven) as he undertakes a massive bet that he can travel the entire world and return within 80 days to his starting location.
The film itself was actually filmed in 75 days in 13 countries and features over 50 cameos by established stars from the era, including Frank Sinatra, Red Skelton, and Peter Lorre. And while there are certainly worse films than this one, Around the World in 80 Days wilts in comparison to three of the films it beat for Best Picture: The King and I, Giant, and The Ten Commandments.
Rent or buy Around the World in 80 Days on Prime Video.7. Out of Africa (1985)
Out of Africa is far from the only Best Picture that seems to drag on and on. But this movie is a slog that could test anyone’s patience.

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