I just learned from this list: Oscar winners: best to worst, that The Maltese Falcon and Citizen Kane came out in the same year, and they both lost to some shit called How Green is My Valley. I haven’t seen the latter but it sounds like a PSA about gonorrhea.
I also thought that Shakespeare in Love beating Saving Private Ryan should have been the #1 unfair win, but Crash was a pretty mediocre movie.
