Top 10 Clint Eastwood Movies

As both a director and actor, Clint Eastwood has been a part of several amazing movies over the course of his more than 60-year career. Amazingly, he’s still working at his advanced age, and is showing no signs of slowing down. He has a new movie out soon, so let’s take a look back at his career.

Here are the top 10 films from the career of Clint Eastwood.

Dirty Harry

There are five Dirty Harry movies. While this might not be the role for which Eastwood is remembered, it’s the one he played the most often – assuming you don’t lump together all of his Western roles, which, in fairness, are often a similar character. Dirty Harry is the first outing for Eastwood as “Dirty” Harry Callahan, a police officer in San Francisco. The case? A copycat of the real-life Zodiac Killer.

It’s also the source of several famous lines, like “Go ahead, make my day” and the monologue that concludes with “Do I feel lucky? Well, do you, punk?.”

Escape from Alcatraz

In 1962, an escape attempt was made by several of the inmates at Alcatraz Federal Penitentiary. None of them – or their bodies – was found. In 1979, a movie was made about it. Escape from Alcatraz is a dramatization of the events that transpired before and during the escape. It’s a very exciting movie – possibly the best prison escape movie ever – and it was actually primarily filmed at Alcatraz, which closed as a prison shortly after the real-life escape attempt.

A Fistful of Dollars

A Fistful of Dollars marked the first leading role for Eastwood, is the initial film in the “Dollars” trilogy, and helped solidify the popularity of the Spaghetti Western subgenre of films. Eastwood plays a character who has no name – who arrives at a small town and basically uses rivalries within it to make a bunch of money. That dynamic is fascinating, and Eastwood’s gruff-and-tough persona really started here.

It’s worth noting that, if you like A Fistful of Dollars, it’s also worth checking out Akira Kurosawa’s Yojimbo, of which it was an unofficial, unlicensed remake. Toho, Yojimbo‘s production company launched a successful lawsuit about it.

For a Few Dollars More

For a Few Dollars More is the second film in the “Dollars” trilogy. All three movies were directed by Sergio Leone and star Eastwood. It’s the most overlooked of the unofficial trilogy, in large part because it’s the middle film – and, while very good, doesn’t quite live up to the freshness of the original or greatness of its successor. It’s tense, occasionally brutal, and a wild ride.

The Good, the Bad, and the Ugly

The Good, the Bad, and the Ugly is a film of epic length and scope – the best of its unofficial trilogy and has at least one scene that’s been parodied to the point that, even if you haven’t seen it, you know it – the Mexican standoff. The film follows three men who are looking for buried Confederate gold, participating in duels and fights over the course of the nearly three-hour running time.

I really enjoy The Good, the Bad, and the Ugly, don’t get me wrong, but if it were tighter and managed to chop off 30 minutes, I can’t say I’d complain.

Gran Torino

Clint Eastwood was supposed to retire from acting with Gran Torino. That didn’t wind up being the case, but it would have been a great end to his acting career. He stars as a Korean War veteran who winds up forming a relationship with a young Korean neighbor after stopping his neighbor from stealing his car – after being pressured by a gang. He winds up acting something like a father figure – but also he’s a Korean War veteran and he’s still pretty racist and jaded. It’s an emotionally and intellectually compelling drama.

High Plains Drifter

High Plains Drifter is kind of a spiritual successor to the work Eastwood did on the “Dollars” trilogy. It was his second directorial outing, and once again starred him as a man without a name – credited as “The Stranger” – who enters a corrupt mining town and starts dealing justice to the evil and corrupt around him – in particular, a trio of outlaws awaiting release from prison. It’s a lot of fun, and it’s interesting to see the elements that Eastwood took from his earlier acting efforts into his version of the Western.

Letters from Iwo Jima

In 2006, Eastwood directed two movies: Flags of Our Fathers and Letters from Iwo Jima. They depict the Battle of Iwo Jima from the two opposing viewpoints. the surprising thing is that the better movie is Letters from Iwo Jima, which tells the story from the Japanese side.

Why is it better? Largely, the characters are stronger. We get a better sense of who they are prior to all the fighting. We know and care about the people involved prior to them having a chance of dying, and that makes it a more emotionally involving film. Flags of Our Fathers is a more guns blazing, “rah rah America!” type of movie. Both are good, and as a two-film project are great, but the better film is Letters from Iwo Jima.

Million Dollar Baby

In terms of boxing movies, Million Dollar Baby ranks near the top. It’s about a woman who, at 32 years old, wants to become a professional fighter. She had no training. She convinces the best trainer around to coach her, even after he says he won’t train girls. And if that sounds like a traditional underdog story, well, it is – for a while. Then it transcends that and becomes a memorable drama. One that I’m not going to spoil, so you’ll have to watch it for yourself.


Unforgiven might wind up as the “best” movie Clint Eastwood ever makes – at least in terms of both starring in and directing. It’s a movie that makes you question the morals of its characters, works a meditation on aging and courage, and effectively makes you question all of the previous Western roles in which you’ve seen its hero. It’s so well made, so engaging, and really does feel like the perfect conclusion to the Western career of Clint Eastwood.