Clint Eastwood has retired, as of 2026, but his final film came at the end of 2024: Juror No. 2. It was his 40th film as a director, and over a span of a little over half a century, he directed a bit of everything, and was even in the director’s chair for two Best Picture winners. Yet even if he’d never directed anything, he’d still be legendary for all the movies he starred in (admittedly, some of those starring roles were in films he also directed, but definitely not all his iconic performances were).
So, in recognition of his best efforts overall, here are five exceptionally high-quality Clint Eastwood movies, with two he starred in without directing, two he starred in and directed, and then one he directed without having any kind of acting role in. These are the Clint Eastwood movies most deserving of being called masterpieces, and if your time is limited, and you want to just focus on the absolute best of the best (and if you somehow haven’t seen any of these before), then they’re all very much worth tackling.
5
‘Dirty Harry’ (1971)
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The whole of the Dirty Harry series is pretty iconic, but it’s the movie that started it all which is comfortably the best. The first sequel, Magnum Force, is also worth an honorable mention. The same goes for Escape from Alcatraz, which isn’t Dirty Harry-related, but it’s also set in (or near?) San Francisco, and it was a collaboration between Eastwood and Don Siegel, with the latter directing Dirty Harry, of course. As for Eastwood’s (kind of) titular character here, it’s probably the most iconic he played in any of his non-Westerns. The Man with No Name is a Western antihero of sorts (and one of his movies will be here shortly), and then Harry Callahan is a bit of a cowboy kind of character out of time; well and truly out of the Old West and all.
Basically, in Dirty Harry (1971), he has to track down a murderer at large dubbed the Scorpio Killer, and he’s pretty much the Zodiac Killer, or at least meant to stand in for the Zodiac Killer. So, Eastwood versus Zodiac is worth the price of admission alone, but then the movie is also interesting beyond the action and thriller elements, since it’s a solid character study and it has something to say about the police and how much might be too much in the pursuit of justice. Or if you just want to enjoy it as a crime movie about fighting fire with fire, then you’re welcome to do that too, of course.
4
‘Million Dollar Baby’ (2004)
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In 2003, Mystic River came out, went dark, and did well, but the next year, Million Dollar Baby ended up being an arguably even better movie directed by Clint Eastwood. It feels like a deconstruction of a typical sports movie; the kind that’s not afraid to look at things realistically and explore the idea that sometimes, the best you can do might not be good enough, because maybe other people are better, or maybe you’re just unlucky and glory wasn’t meant to be. Breaking it down further might make it sound straightforward, and narratively, it is. But it’s all in the execution here, with the skilled direction, amazing performances, and compelling screenplay all working together to make Million Dollar Baby something special.
If you want something uplifting, you’re better off looking for other sports movies, because most are bittersweet at worst, with Million Dollar Baby potentially being about as harrowing as the also great (and utterly depressing) Raging Bull.
It wouldn’t feel like a stretch to call Million Dollar Baby one of the best sports movies of all time, and it’s more than worthy of all the praise that’s been heaped upon it over the years (two decades now and counting). But if you want something uplifting, you’re better off looking for other sports movies, because most are bittersweet at worst, with Million Dollar Baby potentially being about as harrowing as the also great (and utterly depressing) Raging Bull. It’s well-directed and contains one of Eastwood’s best performances, too; also phenomenal here are Hilary Swank and Morgan Freeman.
3
‘Letters from Iwo Jima’ (2006)
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The second part of a duology, with the first part being Flags of Our Fathers, Letters from Iwo Jima is the even stronger half. It’s an unapologetically powerful anti-war film, exploring the Battle of Iwo Jima once more, like Flags of Our Fathers, but it centers on the Japanese perspective instead of the American one, with a little more of a focus on the lead-up to the battle than its aftermath (that’s another way the movies contrast). So, there’s a ton of hopelessness and death throughout Letters from Iwo Jima, making it another upsetting movie to go alongside Mystic River and Million Dollar Baby as a rather upsetting film directed by Eastwood in the 2000s.
Everyone is humanized here, making the villain war itself, which is all quite in line with a good many anti-war movies that don’t bother with having heroes and villains the way more traditional war movies might. Also, Letters from Iwo Jima is admirable in how it works to make Flags of Our Fathers hit harder, too, when one assesses the whole picture and then gets more of an understanding about the truth of the Battle of Iwo Jima and how bad it was for all involved. Yet when you go ahead and judge it individually, Letters from Iwo Jima is the one that hits harder, so it gets the shout-out here rather than Flags of Our Fathers being the one in this spot. There’s no real sentimentalism or anything easy here, but the emotion’s definitely there, and it’s definitely the strongest film Clint Eastwood directed without also acting in.
2
‘Unforgiven’ (1992)
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Image via Warner Bros. PicturesIf you go back a bit further than the 2000s, to the early 1990s, that’s where you’ll find Clint Eastwood’s most impressive achievement as a filmmaker, because that truly exceptional movie is Unforgiven. It’s still something that Eastwood wouldn’t have been able to do quite as well in earlier decades, since you do feel a maturity here, like the director needs to be a bit older, and also, Eastwood had 20+ years of directing experience, so it feels like he drew on all that here. It’s a more brutally honest Western than anything Eastwood had been involved with before, and the characters are all older, too, with Eastwood’s character very much looking at the past and the small amount of time he has left in his future (perhaps enough time to go somewhere toward earning a small sort of redemption).
While Eastwood is great, Gene Hackman does steal the show here, at least if you’re looking at the people in front of the camera, but then it’s also worth shouting out Morgan Freeman and Richard Harris; both are great, and the latter manages to be great with a very small amount of screen time. Behind the camera, Clint Eastwood’s never done better work, and so that’s a big reason why it’s worth considering as one of his grandest masterpieces. Unforgiven is tense, exciting, emotional, surprising, tragic, uncompromising, and also quite entertaining (or at least engaging) all at once. The balancing of all that stuff is impressive, and it manages to do pretty much everything right. On top of being the best-directed Clint Eastwood movie, Unforgiven is also just flat-out one of the greatest Westerns ever made, too… but there is one more Clint Eastwood Western he starred in (albeit without directing) that’s arguably even better.
1
‘The Good, the Bad and the Ugly’ (1966)
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For any category that it could fit into, it can be hard to resist putting The Good, the Bad and the Ugly right near the top, or maybe even at the very top. It was irresistible in this instance. Unforgiven is a more mature film, and it’s impressive in the sense that Eastwood directed it while playing the central character, but there is so much The Good, the Bad and the Ugly does right, and it proves incredibly entertaining, not to mention easy to recommend even to people who might not love Westerns. It’s got a fantastically simple premise, too, since it’s about three entertaining yet morally corrupt (well, they’re different levels of morally shady, as the title implies) characters as they race each other to a fortune of gold buried out in the desert, and then all the while, the Civil War is being fought around them.
A good deal of The Good, the Bad and the Ugly is funny, while other parts are tense, and then even while it’s not dialogue-heavy, there are plenty of incredibly memorable lines. All further praise is just going to continue sounding like hyperbole, but this movie earns it anyway. Eli Wallach and Lee Van Cleef are also great, the Ennio Morricone score is perfect, and Sergio Leone directed the whole thing perfectly. It’s just perfect. It’s The Great, the Far-From Bad and the Masterful. It’s everything you could want out of a Western and more, making it the best film Eastwood was ever part of in one way or another.
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