5. Million Dollar Baby (2004)
Million Dollar Baby stars Hillary Swank as a woman desperate to become a professional boxer. She's a little past her physical prime and comes from a very poor background. Clint Eastwood plays a hardened trainer that "Doesn't train girls," and insists that she'll never be able to make it. If you haven't seen the movie I know what you're thinking now: it's an old, clichéd story. Well, you're wrong. It won four Academy Awards, and what a set of four that was: Best Picture, Best Director (Clint's second time winning that double), Best Actress in a leading role (for Swank) and best supporting actor (oh yeah, Morgan Freeman is in it too). It's the first movie in this list with Clint Eastwood both directing and starring (he was also nominated for an Academy Award for his acting). If you haven't seen it yet; scroll down and hit "next" right now. Bookmark this page and look at it after you've seen the movie (which you should do as soon as possible). If you have seen it, then of course it's safe to read on for why I think that it's fifth in such a great filmography. The acting is completely deserving of the awards it received and the major reason that it isn't that cheesy old thing that it appears to be is the twist towards the end and the complete tonal shift following that. I'm not sure that the image of Frank trying (and failing) to reach into the ring and pull the stool out of the way will ever leave my mind.