To me Clint Eastwood is first and foremost an actor, but it's becoming harder and harder to ignore the immense body of directorial work he's done. So far Eastwood directed 35 feature films spanning 45 years. That's more than most directors would hope to ever accomplish in their entire career. Even though he's well in his eighties now, he's not showing signs of slowing down anytime soon.
To say I dislike Eastwood's film would be an understatement. I'm not particularly fond of westerns and his sentimental dramas don't really do it for me either. Eastwood is one of those directors who ended up on my list mostly by accident, by watching a few of his well-respected films combined with some random encounters. Not counting one pleasant surprise, his oeuvre has left me pretty disappointed.
The oldest Eastwood I've seen is High Plains Drifter, one of the first films where he appeared as director. It's a pretty typical western on the surface, though I'm sure western fans will appreciate the deeper layer underneath. If you're like me and you don't like the typical western elements (not in the least Eastwood's character), the film has very few redeeming qualities. The same could be said about Unforgiven, the second Eastwood I've seen. In between he made 11 more films, though none of which I've seen.
In 2003 Eastwood released Mystic River, the film that kickstarted the most recent cycle in his career. It's a very heavy-handed, sentimental and drab Hollywood drama that would go on to become the template for most of his later films. Millon Dollar Baby and Changling suffer from the same shortcomings, while Letters from Iwo Jima and American Sniper carry over the defect to a war-like setting. Jersey Boys (adapted from the musical) doesn't fare much better.
The only Eastwood film I liked so far is Gran Torino. Not that I have extremely fond memories of it, but the main character is just perfect for Eastwood's onscreen persona. It is easy to see how the film could be pretty offensive to some (Eastwood's character has been wrongly branded a racist and the film's ending is pretty boastful), but as long as you see the humor of his performance then it's an okay film.
Long story short, Eastwood isn't my kind of director (nor actor for that matter). I find his films old-fashioned, dire, heavy-handed and lifeless. I still have a few Eastwoods lined up, but only because of their status. If you're into westerns than a film like Unforgiven is a good starting point, if you're more into Hollywood drama then Mystic River is the obvious choice.
Best film: Gran Torino (3.5*)
Worst film: High Plains Drifter (0.5*)
Average rating: 1.25 (out of 5)