8. Unforgiven
I'm obviously a huge fan of Clint Eastwood's directorial work, and this is the one that put him on the map. Not only is this film the best western ever made, it is one of my favorite films of all-time. The story is brilliant. The cast is brilliant, with great performances from Clint Eastwood, Morgan Freeman, Richard Harris, and one of my favorite villians of all time with Gene Hackman's performance. In particular, the ending is absolutely brilliant and one of my favorite endings to a film of all-time. This revenge flick I can watch over and over and learn new things about the film everytime. Bravo Eastwood!
7. Million Dollar Baby
Back to back with Eastwood here. Ultimately my favorite "sports" flick of all time. Some of the best behind the camera work that I have ever seen in cinema, Eastwood makes me feel a certain emotional attachment to the characters. Hilary Swank puts in the best performance by an actress OF ALL TIME for me, playing a character with nothing to lose but everything to gain. Morgan Freeman gives a fantastic supporting performance, and, other than possibly Gran Torino, this is my favorite acting performance from Eastwood. The film catches a lot of flack but it is great in so many ways to me that I don't really care about the flaws that it may have.
6. Casablanca
This film has shot up because, well, because it is a really great film. We don't see acting performances like this anymore. Hell, we rarely see brilliant stories like this anymore. If this is classified as a romance drama, it is my favorite. Michael Curtiz directs the film brilliantly, and of course all-time great performances put in by Ingrid Bergman, who can really really act, and an all time legend in Humphrey Bogart. The film is mid-40s but it hasn't aged a bit. A big part of that is the dialogue to the film, there are so many quotable pieces in this film. Brilliant from beginning to end.
5. Gone Baby Gone
Ben Affleck's directing debut is hands down the best debut I've ever seen. He took Dennis Lehane's novel and made a filming masterpiece. The casting choices were brilliant, with Casey Affleck, Michelle Monahan, Morgan Freeman, Ed Harris, and Amy Ryan, among the many other supporting characters. The beginning of the film strikes me the most, one of the most moving beginnings that I have seen to a film. The cast as a whole had great chemistry with each other, and the camera work of Boston is nothing short of splendid. A truly underrated film on this forum and just in general.