2. Gran Torino
Personally, I’d love to put Gran Torino at number one (it’s my favorite of Eastwood’s films), but I know that wouldn’t be right. So here it sits at number two, beating out the likes of Unforgiven and Mystic River. And if you want to know why I put it this high up on this list, here is my answer: evolution. Yes, for me Gran Torino, more than any other film on this list, shows Eastwood’s evolution as a director. Gran Torino has a very similar tone to many of Eastwood’s other films, most specifically his Westerns, but what I love about the movie is how it takes the tough guy, growling grittiness of Eastwood’s earlier work and uses it show us something more optimistic – the possibility of finding the bonds of family with those who may not actually be a part of your own. To me, Gran Torino is Eastwood nostalgically acknowledging the past while impressively looking towards the future.
Photo by Theo Wargo/Getty Images for Tony Awards Productions