10. The King's Speech, 2010
Only time will tell whether this was a controversial choice. David Fincher's The Social Network, about the founding of Facebook, was surprising, innovative and possessed of a unique directorial vision. The King's Speech, a solid effort, was none of those things. Its win was the Academy's safest choice in many years, and that's saying something.
9. Around the World in 80 Days, 1956
Just try sitting through all 167 minutes of this turgid Jules Verne adaptation today, one of the worst movies ever to win Best Picture (and whatever you do, stay away from the 2004 remake). Strong motion pictures were few and far between in 1956, although looking back, the sprawling Texas saga Giant seems like it should've been the obvious choice for the top prize.
8. Chicago, 2002
Movie musicals enjoyed a bit of a boom around the turn of the millennium, which peaked with this Oscar win. It was a year late. Chicago, while featuring a handful of show-stopping moments, was a flat film. Baz Luhrmann's Moulin Rouge, however, truly did shake up the genre. It was nominated for eight Oscars, but won only two in technical categories.
7. Forrest Gump, 1994
This Tom Hanks movie was very popular, but the guffaws erupted as soon as it won Best Picture. Why? Well, it's kind of dopey. And consider what got passed up — The Shawshank Redemption, a sentimental prison flick that everyone still seems to love, and the groundbreaking Pulp Fiction, the high-water mark (so far) for auteur Quentin Tarantino.
6. Crash, 2005
This was not a proud night for the Academy. The intermittently compelling Crash was a deeply flawed film, but it didn't feature two homosexual men at its core. The cowboy romance Brokeback Mountain broke new ground in mainstreaming gay relationships (in addition to being the better film, which is all that really matters), but a majority of Academy voters had another agenda.
5. How Green Was My Valley, 1941
John Ford's Oscar winner about a family in a Welsh mining town has looked and felt like sentimental schmaltz since the day it was released. Another nominated picture that year, Citizen Kane, has been widely regarded for several decades now as one of the best American films ever made. A no-brainer.
4. Midnight Cowboy, 1969
The Academy deserves a lot of credit for choosing this raw, X-rated picture for the Oscar, but the movie is seldom seen today. Nominee Butch Cassidy and the Sundance Kid has enjoyed a much longer life. The obvious choice for Best Picture this year, however, should've been Stanley Kubrick's seminal 2001: A Space Odyssey, but it wasn't even nominated. Kubrick, however, did take home the only Oscar of his career, for Best Visual Effects.
3. Dances With Wolves, 1990
Martin Scorsese's mobster classic Goodfellas was overlooked for a western with hipster sensibilities that feels tonally awkward today. Scorsese would finally win it all in 2007 with The Departed, a very decent but minor film.
2. Ordinary People, 1980
Robert Redford's family drama, co-starring Donald Sutherland and Mary Tyler Moore, has been blasted for years for stealing the Oscar from Scorsese's Raging Bull. The criticism is just; the latter, starring Robert De Niro as a boxer, is a far superior film. But Ordinary People wears its Academy Award well, and has only improved with age.
1. Shakespeare in Love, 1998
It was perhaps the biggest Oscar upset in modern times. Saving Private Ryan, Steven Spielberg's World War II epic, was the clear favorite. But the filmmaker had already won it all in 1994 for another WWII film, Schindler's List. And Harvey Weinstein, Shakespeare in Love's producer, mounted an Oscar campaign for the ages. Voters ate it up.