If you look over all the Oscar winners for Best Picture from 1927 to 2005, you might assume that it's a pretty good list of movies, and indeed, some of them are. But if you really start digging and considering the other nominees, or even worse, the movies that didn't get nominated, then the system starts to fall apart.
For example, does anyone these days truly believe that Shakespeare in Love was a better movie in 1998 than Saving Private Ryan, The Thin Red Line, The Truman Show, Out of Sight, The Big Lebowski or Rushmore?
Here are a few of the most obvious examples: The English Patient beats Fargo in 1996; Dances With Wolves beats GoodFellas in 1990; Ordinary People beats Raging Bull in 1980. But let's go back a little farther. Driving Miss Daisy won in 1989, while neither Spike Lee's Do the Right Thing nor Woody Allen's Crimes and Misdemeanors were nominated. Out of Africa won in 1985, while Terry Gilliam's Brazil wasn't nominated. Oliver! won in 1968, while Kubrick's 2001: A Space Odyssey wasn't nominated. In the Heat of the Night beat both Bonnie and Clyde and The Graduate in 1967. Gigi won in 1958, and Hitchcock's Vertigo wasn't nominated. Around the World in 80 Days won in 1956, while John Ford's The Searcherswasn't nominated. The Great Ziegfeld won in 1936 and Chaplin's Modern Times was not nominated. I could give an obvious example for practically every year, but you get the picture.