Let’s face facts: when most of us think about “Western,” the first thing to pop into our heads is Clint Eastwood squinting in the sunlight, poncho blowing, hand resting on his gun. For over sixty years, he’s been the genre’s face—sometimes as a brooding wanderer, sometimes as a tough criminal, and yes, even as a singing prospector (yes, it’s a thing). Few have personified the West as Eastwood has. Saddle up, then—here’s my completely subjective countdown of Clint’s ten best Westerns, from “solidly entertaining” to “all-time classic.”
10. Paint Your Wagon (1969)
Ever curious what it would be like to see Clint Eastwood swap guns for a songbook? Meet Paint Your Wagon. Playing Pardner opposite Lee Marvin and Jean Seberg, Clint has a surprisingly fine singing voice and even some comical talent. The film is campy, slightly odd, and not what one expects from an Eastwood film—but that’s precisely what makes it so much fun. Evidence that the man could do more than just glare and shoot.
9. Joe Kidd (1972)
Starring as ex-bounty hunter Joe Kidd, Eastwood is caught up in a land war between impoverished peasants and a cruel land baron, played by Robert Duvall. The film itself is fairly simple, but Eastwood infuses it with his characteristic intensity and understated presence. It’s not his most iconic performance, but it’s sufficient for a slab of early ’70s Westerngrime.
8. Cry Macho (2021)
Who tells cowboys that they, too, have an expiration date? Back at 91, Eastwood returns with Cry Macho, playing Mike Milo, a retired rodeo rider sent on a road trip across Mexico. Unlike his young, gun-toting protagonists, Mike is reflective, kind, and seeking redemption. Looking at Eastwood here is like looking at the genre itself, glancing back over its long, dusty trail. A low-key, late-period gem.
7. Two Mules for Sister Sara (1970)
This teams Eastwood up with Shirley MacLaine on an improbable buddy comedy. He is Hogan, a war contractor who assists what seems to be a nun, although she ain’t precisely what she claims to be. Their banter and chemistry keep it light, though Clint still brings the roughness we’re used to. It is witty, sporty, and just quirky enough to hold on its own in his Western tradition.
6. Hang ‘Em High (1968)
After the spaghetti Western success, Eastwood played Jed Cooper, a marshal who narrowly escapes being hanged and goes in search of vengeance. This is significant in that Clint is not invulnerable—tough, of course, but also stumbling, bleeding, and continuing. It’s a revenge story with genuine depth, and Eastwood gets away with it on searing conviction.
5. Pale Rider (1985)
In Pale Rider, Eastwood wears the collar of a cryptic preacher who rides into a mining town to protect it from brutal corporate interests. But is he a man—or some kind of supernatural being, e.g., ghost or vengeful spirit? The mystery makes this one of his best performances. Audiences evidently agreed: it was the biggest ’80s Western hit.
4. For a Few Dollars More (1965)
The second film in Sergio Leone’s legendary Dollars Trilogy reunites Eastwood’s “Man With No Name” with Lee Van Cleef for some unforgettable bounty-hunting. The bad guy is terrifying, the shootouts are thrilling, and Ennio Morricone’s theme music is simply legendary. Eastwood and Van Cleef’s tense chemistry turns this one into a genre classic.
3. The Outlaw Josey Wales (1976)
That’s where Eastwood began to redefine the Western. As Josey Wales, a Missouri farmhand turned outlaw after his family is massacred by Union troops, Clint gives a nuanced, commanding performance. The film is revisionist, hard-boiled, and deeply personal, solidifying Eastwood as more than just a cowboy icon, proving that he could both act and direct a story of substance.
2. Unforgiven (1992)
Eastwood’s magnum opus as an actor and director. In the role of William Munny, a retired gunslinger who is returned to duty for one last job, Eastwood shatters the fantasy of the cowboy. Raw, reflective, violent—a film about violence and morals—the movie is not surprisingly Eastwood’s Oscar-winning one.
1. The Good, the Bad and the Ugly (1966)
Was there ever any doubt? Leone’s masterpiece remains the spaghetti Western, Eastwood’s cigar-chomping drifter the ultimate antihero. Couple that with Civil War-era setting, Eli Wallach’s unforgettable Tuco, Van Cleef’s merciless Angel Eyes, and Morricone’s unforgettable score, and it’s cinematic magic. If you’re only going to watch one Clint Eastwood Western, make it this.
Clint Eastwood didn’t merely act in Westerns—he created them, remade them, and rode them into modern times. Whether he’s crooning, plotting, or glowering at you from beneath the brim of that hat, one thing’s for sure: nobody gets the dusty trail done quite like Clint.