Clint Eastwood has been in the public eye since the 1950s when he first starred as Rowdy Yates in the Western television drama Rawhide. From there he became a household name as a Western star before leaving the genre behind and become a Hollywood superstar as both an actor and director. Even at the ripe old age of 91, Eastwood is still getting it done, with his next directorial feature (set to premiere this fall) a neo-Western called Cry Macho.
Eastwood’s legacy is extensive. His iconic roles such as the Man With No Name, Harry Callahan, Walt Kowalski, and Will Munny will long outlive the legend, and his time behind the director’s chair will forever go down as “inspired” throughout film history. While we unfortunately can’t list every Eastwood flick out there, know that these are some of his best well worth your time.
1. Unforgiven (1992)
Unforgiven is one of the all-time greatest westerns (you can check out our favorites here). Eastwood stars and directs in this final send-off to his work in the Western genre. Eastwood plays Will Munny, a former gunslinger and widower forced to raise his two children on his own while confronting his dark past.
This film features some of the most incredible performances from Gene Hackman (Enemy of the State), Morgan Freeman (The Shawshank Redemption), Richard Harris (Harry Potter and the Sorcerer’s Stone), and Eastwood himself, who insert their hearts and souls into each and every frame. It’s their work in the film that sets it apart from not only all of Eastwood’s other Westerns but also his entire filmography.
To this day, Unforgiven features not only Eastwood’s greatest performance but his best work behind the camera. A cinematic masterpiece.
2. Dirty Harry (1971)
Arguably Eastwood’s most popular role, Dirty Harry features San Francisco homicide inspector Harry Callahan as he tracks down the serial killer Scorpio (who is loosely based on the Zodiac Killer) using some messy and unorthodox methods. The film inspired a series of Dirty Harry pictures and is responsible for the immortal line, “Do I feel lucky? Well, do ya punk!”
Eastwood would later go on to direct the fourth film, Sudden Impact, in the five-picture series, but the original film is where the magic started. The bank robbery scene alone (which takes place in the first act) is worth the watch.
Harry’s “no care” attitude and “tough on crime” outlook will both entertain and scare you until the film cuts to black. Dirty Harry is one of the best cop thrillers out there, so if you like neo-noir action thrillers, this one is for you.
3. The Dollars Trilogy (1964, 1965, & 1966)
The film series where the Man With No Name comes from, Eastwood stars in all three of Sergio Leone’s infamous Spaghetti Westerns: A Fistful of Dollars, A Few Dollars More, and the aptly titled The Good, The Bad, and The Ugly, which make up what’s collectively known as The Dollars Trilogy.
While the first two are incredible, the third film, in particular, shines as one of the greatest Westerns of all time. It features one of the all-time gunfights ever committed to celluloid and is known for helping make the Mexican Standoff an action movie cliche.
Eastwood’s Man With No Name might even be the most iconic gunslinger of them all. The Dollars Trilogy might not feel like a John Wayne Western, but, like the Man With No Name himself, it gets the job done.
4. Gran Torino (2008)
Another of Eastwood’s finest performances, and, if Unforgiven weren’t so darn good, is among his best-directed films as well. Gran Torino is about a recently widowed Koren War veteran, Walt Kowalski, who befriends the two young Hmong Americans, Thao (Bee Vang) and Sue (Ahney Her) who live next door.
While the film has sparked controversy due to its racist dialogue (though, that’s kind of the point as Kowalski learns to overcome his own racial prejudices), it’s still praised today for its themes of friendship, overcoming racism, and for being the first major American film production to have a large Hmong cast. While this may seem like a film that your dad would want you to watch, Gran Torino is a modern masterpiece worth your time and attention.
5. Play Misty For Me (1971)
Eastwood’s directorial debut, Play Misty For Me is a psychological thriller that’s often forgotten when one reminisces on the filmmaker’s filmography. This movie features Eastwood opposite the late Jessica Walter (Arrested Development) as a radio disc jockey who is being stalked by an obsessive fan.
While we might be used to Walter as an emotional manipulator on television, her role in Play Misty For Me brings it to an entirely new level. Her performance stands out and earned her a Golden Globe nomination that year. Play Misty For Me is one of Eastwood’s hidden gems that deserves a bigger audience.
6. American Sniper (2014)
The first film on this list not to star Clint Eastwood in any capacity (though he does appear in a cameo as a “Churchgoer”), American Sniper stars Bradley Cooper (A Star Is Born) as real-life U.S. sniper Chris Kyle, who became the United States most deadly marksman with over 255 kills in the Iraq War.
American Sniper is some of Eastwood’s finest work as a film director as he shows the heaviness, ugliness, and brutality of modern warfare. If you think war is like Call of Duty, you’re dead wrong, and this film will prove that. While this might be a lot for some to watch, it’s an important film that deals with issues of mental health and veteran’s affairs. American Sniper is one of the only films this writer walked out of in complete silence, with not one audience member uttering a word.
7. The Outlaw Josey Wales (1976)
Set both during and after the American Civil War, The Outlaw Josey Wales stars Eastwood as, you guessed it, Josey Wales, a Missouri farmer who seeks revenge on those who killed his family, only to be pursued by Union soldiers. It’s about what you’d expect from an Eastwood Western.
Back in 2011, Eastwood went on record stating that Josey Wales is an “anti-war film,” saying that “everybody gets tired of it, but it never ends.” This is seen clearly throughout the film as even when the Civil War ends, Josey’s war never does.
Even once his quest is “complete” he’s still on the run. His war is never truly over. To this day, The Outlaw Josey Wales is one of the most beloved Eastwood films by fans and critics alike.
8. Million Dollar Baby (2004)
Eastwood’s critically acclaimed sports drama is not for the faint of heart. Eastwood stars as Frankie Dunn, a gruff boxer-trainer, alongside Hilary Swank (The Next Karate Kid) as Maggie, an aspiring boxer, and Morgan Freeman as Dunn’s assistant (and the film’s narrator). This movie is ultimately about family, and we love that.
Frankie and Maggie’s relationship is the cornerstone of this film. Maggie’s poor relationship with her family juxtaposes with Frankie’s, allowing them to form a familial bond of their own. Million Dollar Baby is a heart-crushing tale about following your dreams and working like hell to catch them.
9. High Plains Drifter (1973)
Influenced by the work of his longtime collaborators and mentors (who he actually dedicated Unforgiven to) Sergio Leone (The Dollars Trilogy) and Don Siegel (Dirty Harry), High Plains Drifter is a Western directed by (and starring) Clint Eastwood about a mysterious Stranger who executes justice in a corrupt frontier mining town.
Simple plot aside, others, such as Western icon John Wayne (The Searchers) didn’t take to Eastwood’s iconoclastic approach, even going so far as to write him a letter stating that “this wasn’t what the West was about.” Wayne’s critique aside, the film manages to keep folks entertained and happy to this day. High Plains Drifter is the gunslinging ghost story that you didn’t even know you craved, and that’s what we love about it.
10. Escape From Alcatraz (1979)
The final collaboration between Eastwood and director Don Siegel, Escape From Alcatraz is a prison action film that’s exactly what the title suggests as it dramatizes the historical 1962 prisoner escape from the maximum-security island.
Eastwood plays Frank Morris, a real-life convict from the riots with an exceptional I.Q. who works hard to break free from his bonds. While the final scene implies that part of the escape may have been successful, it has since been debated if anyone actually succeeded or not. Escape From Alcatraz may not be the usual Clint Eastwood film, but that’s part of its charm.
11. Flags of Our Fathers/Letters from Iwo Jima (2006)
This double feature is an exceptional look into Eastwood’s work as a director. Flags of Our Fathers chronicles the five Marines and one Navy corpsman who were involved in raising the American flag on Iwo Jima and how that drastically affected their lives. It’s a truly patriotic film that, like American Sniper, can show the ugliness of war.
On the flip side, Letters from Iwo Jima, which was filmed back-to-back with Flags of Our Fathers as a companion piece, is almost entirely in Japanese as it follows the same World War II battle from a Japanese point of view. Flags of Our Fathers and Letters from Iwo Jima may be Eastwood’s most important films to date, showing two perspectives on the same events, reminding us that everyone has something they believe is worth fighting for.
12. Pale Rider (1981)
A soft remake of the Western classic Shane, Pale Rider is one of Eastwood’s most interesting Westerns as it takes the classic Western formula and adds a revisionist spin to it. Eastwood also stars as “the Preacher” (as he wears a clerical collar), who is modeled after the “pale rider” in the Book of Revelation, the Horseman of Death.
Unlike Shane, Eastwood’s Pale Rider doesn’t shy away from the Preacher’s desires, nor does he shy away from violence as he works to protect the snowy mountain town and the family that he has come to love. So much so that he has both mother and daughter vying for his attention (which is a little strange and uncomfortable). Pale Rider does the work of a revisionist Western by de-mystifying the American West.
13. The Gauntlet (1977)
Another Eastwood-directed picture that stars the Hollywood icon as a down-and-out cop who falls in love with a prostitute (Sondra Locke, The Outlaw Josey Wales) he is assigned to escort from Las Vegas to Phoenix so she can testify against the mob.
While the poster might seem to promise a “post-apocalyptic thriller,” The Gauntlet is a more down-to-earth action film that features your usual high-speed pursuits. Though, there is a helicopter crash sequence that’s pretty cool. If you like the gangster stuff and want to see some folks fight the mob first-hand, The Gauntlet is the Clint Eastwood flick for you.
14. Mystic River (2003)
Although Clint Eastwood doesn’t appear on-camera in this one, Mystic River is one of his most interesting films behind the camera. Besides the fact that it’s the first film he received credit for composing, it’s also the first time a film won Best Actor and Best Supporting Actor at the Oscars since Ben-Hur in the 1950s.
Mystic River is the story of three men who were childhood friends as their lives are shattered after one of them experiences a family tragedy. If that sounds vague and suspicious, it should, because if we say anything else it’ll spoil the whole thing. If you’re unsure about Mystic River, let the cast of Sean Penn (The Game), Tim Robbins (The Shawshank Redemption), and Kevin Bacon (The Following) convince you.
15. In the Line of Fire (1993)
Clint Eastwood might not be the first name you think of when you hear “political action thriller,” but maybe it should after seeing In the Line of Fire. Eastwood stars as Secret Service Agent Frank Horrigan as he attempts to take down a man going by the name “Booth” (John Malkovich, Of Mice and Men) before he assassinates the President.
The combination of politics, suspense, and action sequences will keep you engaged and entertained for the entirety of the film. Eastwood delivers, with help from Rene Russo (Lethal Weapon 3) who plays his Secret Service partner, as he fights to keep the President out of the line of fire. In the Line of Fire isn’t the most popular Clint Eastwood movie, but it does remain one of his most overlooked roles.
16. The Mule (2018)
A more recent addition to Eastwood’s filmography, both as an actor and a director, The Mule is based on a real-life story in which Leo Sharp (renamed Earl Stone in the film), a former WWII vet, became a drug mule for the Sinaloa Drug Cartel. Eastwood, in his 90s, gives one of the most interesting performances of his career, and we love it.
With a killer cast including Bradley Cooper, Laurence Fishburn (Mystic River), Michael Pena (Million Dollar Baby), Diane Wiest (Life In Pieces), and Andy Garcia (Ocean’s Eleven), The Mule is a well-intentioned look at the life of a family man with nowhere to go but down, and it’s certainly worth the ride. The Mule has been called a “poignant and charming” film, and that should be enough to peak your interest.