5. The Departed
Martin Scorsese should've won an Oscar much earlier in his career - losing out to Dances with Wolves when he had Goodfellas was shocking. The Departed is proof that filmmakers can not only remake a foreign film exceptionally well, but additionally, if they are good enough they will eventually win an Oscar. An incredible cast, a hugely entertaining film - this is an example when Oscar gets it right and everyone who watches the film will agree with their decision
4. Annie Hall
Oscar is not a big fan of comedy. I am a huge fan of Woody Allen and Annie Hall is much more accessible than the vast majority of his work. Even with Manhattan, Woody Allen has the semi-pretentiousness of a black-and-white palette whilst one of the female love interests to Woody is a 14-year-old girl. You get none of this in Annie Hall, just some incredible jokes and some facsinating innovative techniques in use - subtitles to expain what the couple really mean, tthe ghost-like Diane-Keaton leaving the bed as Woody tries to seduce her whilst the opening and closing direct-to-camera monologues show how great a showman Woody Allen truly is.
2. West Side Story