It's been a while since I've watched a Best Picture Winner for my quest, but I finally did not long ago... Cavalcade.
I'll just keep this short and sweet. I didn't find it all that entertaining, and it was more like a movie that patched together historically significant events and replayed them through the eyes of two different families (one that was well-off, and another that was struggling).
However, the movie did not attempt to show how different these views were really. Like, it wasn't as if there were any large differences between the two. The film is titled appropriately... overall, the movie just wanted to show some U.S. history from 1900 to 1933.
I probably didn't appreciate it the way that I should have, but seriously, it just wasn't all that entertaining. If you want to enjoy a historical cavalcade put into a 'entertaining' movie, I suggest you just watch Forrest Gump instead.