3. The Broadway Melody (1929)
The truth: The first "talkie," and the first musical, to win Best Picture ought to be something more memorable. But, man, this is a stinker. There's actually very little singing and dancing, despite the title, and when there is music it's the same damn song. There are plenty of movies from this era that are lively and gay, but this ain't one of them: It's a chore.
What should have won: Our vote is for The Patriot, because it was directed by Ernst Lubitsch and starred the great Emil Jannings as Czar Paul I. It has, however, been lost (the only such Oscar nominee in history), only elevating it in our esteem.