Sometimes the best film doesn’t win the Oscar, but the winner is still quite good (examples: From 1994, Pulp Fiction is one of my favorite films, but the winner, Forrest Gump, is still a really good movie. Alternatively, in 1977 Star Wars lost, but Annie Hall is Woodie Allen’s best ).
Other times, the winner isn’t a great film, but there were no other candidates that stand out as particularly deserving (example: in 1995, Braveheart isn’t very good, but the other nominees were Apollo 13, Babe, Il Postino, and Sense and Sensibilities.)
So after going back through time, here are my top 5 examples of clearly worse movies beating better ones.
Actually won: Shakespeare in Love
Should have won: Saving Private Ryan
Actually won: Crash
Should have won: Brokeback Mountain
Actually won: The English Patient
Should have won: Fargo
Actually won: How Green Was My Valley
Should have won: Citizen Kane
Actually won: Ordinary People
Should have won: Raging Bull