If you’ve watched movies anytime in the past six decades, chances are you’ve seen Clint Eastwood glower at an enemy, deliver a line that instantly became iconic, or direct a story that leaves you questioning right and wrong. Few Hollywood careers have stretched as far or evolved as dramatically: from TV cowboy to spaghetti Western gunslinger, to one of the most respected directors working today. And at 94, he still hasn’t ridden off into the sunset officially. So, let’s count down the 10 greatest Clint Eastwood-directed films from “great” to necessary.”
10. Mystic River (2003)
Eastwood adapted Dennis Lehane’s book into a harrowing drama of childhood trauma, killing, and wounds that do not heal. Strongly supported by acting powerhouses, including Sean Penn, Tim Robbins, and Kevin Bacon, Mystic River is one of Eastwood’s darkest, most chilling films. Penn and Robbins each received Oscars, and Eastwood himself received a directing nomination.
9. The Bridges of Madison County (1995)
No one figured that Dirty Harry guy Clint Eastwood was going to helm one of the most heart-wrenching romances of the 1990s. But that’s precisely what he did, co-starring with Meryl Streep in this story of a brief love affair. What might have been a soap opera was instead a profoundly emotional tale even jaded critics couldn’t help but show some respect for.
8. Million Dollar Baby (2004)
Just when folks believed the boxing genre had said all it had to say, Eastwood came along and threw a knockout punch. As a crusty old trainer opposite Hilary Swank’s plucky underdog, Eastwood directed a picture that left viewers stunned. It mopped up at the Oscars—taking Best Picture, Best Director, Best Actress, and Best Supporting Actor, and is still one of the most gut-busting dramas of his career.
7. The Outlaw Josey Wales (1976)
This post-Civil War Western solidified Eastwood as an actor beyond the action hero. Playing Josey Wales, a farmer-turned-outlaw, Eastwood injected grit, gravitas, and unexpected tenderness. The film isn’t about revenge; it’s about unlikely family and redemption. A classic 1970s Western, and one of Clint’s best roles.
6. Letters from Iwo Jima (2006)
In a bold move, Eastwood narrated the Battle of Iwo Jima from the enemy’s point of view. The outcome was one of the strongest anti-war movies in contemporary film. Subdued, compassionate, and heartbreaking, Letters from Iwo Jima humanized “the other side” in a manner that few Hollywood war movies ever try to.
5. Honkytonk Man (1982)
One of the less noisy films in Eastwood’s roster, Honkytonk Man is a Depression-era road movie in which he shares the spotlight with his son, Kyle. Portraying a country singer on his way out who is seeking one last chance at stardom, Eastwood demonstrated a surprising gentleness both in acting and directing. A melancholy treasure that critics loved, although audiences neglected it.
4. Pale Rider (1985)
In the midst of a decade when Westerns had all but vanished, Eastwood provided a box office sensation that demonstrated the genre still lived. As a mysterious preacher who rides into town to stand up for a group of miners, Eastwood combined the spiritual with the stoic. It was the most successful Western of the 1980s and a reminder that he was still the master of the genre.
3. Juror #2 (2024)
Even at 90, Eastwood remains active, churning out films. Juror #2 features Nicholas Hoult as a man who sits on a murder trial and comes to realize, gradually, that he himself might be guilty of the crime in question. Critics loved the tension and moral ambiguity of the film, deeming it one of Eastwood’s best late-era efforts. If indeed this is his last film, then it’s one hell of a swan song.
2. High Plains Drifter (1973)
Eastwood’s second directorial feature is a ghostly, near-surreal Western. Playing a nameless drifter who comes into a crooked town to mete out justice, he deflects the distinction between man and legend. Stranger and darker than the Westerns in which he had previously starred, it demonstrated that Eastwood was not afraid to take risks and outraged John Wayne in the process.
1. Unforgiven (1992)
The defining work of Clint Eastwood’s directorial career. With Unforgiven, he deconstructed the legends of the American West, recounting the tale of an old outlaw lured into one final gig. Bleak, brutal, and suffused with humanity, it took home four Oscars, among them Best Picture and Best Director. Not a Western so much as a meditation on violence, on morality, and on time passing, it’s an irrefutable masterwork.
Clint Eastwood’s acting and directing career is as diverse as it is impressive, embracing Westerns, romances, war dramas, and everything in between. Either wielding a six-shooter or the camera, he’s left a legacy of film history that few have been able to surpass. If, indeed, this is the twilight of his career, one thing is for sure: Eastwood has already solidified his position as one of cinema’s great legends.