Oscars: Top 10 Worst Best Picture Winners

7. Shakespeare in Love, John Madden, 1999

When I finally got around to seeing Shakespeare in Love a few years ago, I was stunned. Holy crap, this isn’t actually a terrible movie. But it’s also not a very good one. Shakespeare is a light-hearted look at Elizabethan England through the eyes of a womanizing Shakespeare, played by the now-struggling-to-find-a-job Joseph Fiennes.

The other issue with the film - aside from stealing Saving Private Ryan’s Best Picture award - is that it also stole its two acting wins. As much as we all love Judi Dench, we all must admit that she should have an Oscar resume for some of her greater, longer roles and not the cameo she has here. And Gwyneth Paltrow’s Best Actress win was just undeserved.

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