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Dirty Harry
Warner Bros
“You’ve got to ask yourself one question: 'Do I feel lucky?' Well, do you, punk?” You can just hear Clint saying that iconic line, can’t you? The rest of the movie is pretty damn awesome as well. We’ve seen a lot of tough guys with a vendetta on the big screen, but it doesn’t get much cooler than Clint’s Harry Callahan.
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Million Dollar Baby
Warner Bros
Just thinking about this film should just crush you. It’s a film that pulls the rug out from under you and just devastates you, and it rightly won Best Picture, Best Actress for Hilary Swank, and Best Supporting Actor for Morgan Freeman. Clint came oh so close to winning his first Best Actor Oscar (he lost to Jamie Foxx in “Ray”).
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Unforgiven
Warner Bros
Every western since has been compared to Clint’s 1992 take. After a career full of them, Clint said it would be his last western, and he certainly chose a good one to go out on. It won four Oscars, including Best Picture, and Best Director for Clint.
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The Good, Bad And The Ugly
United Artists
The 1966 epic spaghetti western is credited as catapulting Clint into stardom. It was the third instalment of the “Dollars” trilogy, with Clint playing one of three gunslingers racing to find some gold.
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Mystic River
Warner Bros
Clint stayed behind the camera for this one, but man, what a cast he had. Playing childhood friends brought back together by a murder investigation, Sean Penn and Tim Robbins both won Oscars, and are supported by Kevin Bacon, Marcia Gay Harden, and Laura Linney, who delivers a wallop of a final scene.
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The Bridges Of Madison County
Warner Bros
While Clint is mostly known for starring and directing “tough guy” films, he surprised us all with his delicate adaptation of the bestselling book. He gives one of his best performances alongside Meryl Streep (well, you gotta bring your A-game going up against Meryl) for one of the most memorable romance films ever.
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A Fistful Of Dollars
United Artists
You could literally make a “Best Of Clint Eastwood” list and just include westerns, and on it you would find this film. I mean, when Clint’s character is called “Man With No Name”, you know it’s awesome. He’s mysterious. He wears a cowboy hat. He shoots a gun. It’s a classic.
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A Perfect World
Warner Bros
If Clint is going to be in a movie, he’s usually playing the lead, but this time round, he took the supporting role as a Texas Ranger. Kevin Costner and Laura Dern star in a crime-drama about a convict on the run with a young boy. The film continued Clint’s 1990s winning streak.
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Letters From Iwo Jima/ Flags Of Our Fathers
Warner Bros.
At 76 years old, Clint took on the task of bringing these companion films to the big screen. “Flags Of Our Fathers” told the story of the 1945 Battle of Iwo Jima while “Letters From Iwo Jima” (released two months later) told the same story from the Japanese point of view. Just getting these films completed is an incredible accomplishment. The fact that they are fantastic films (“Letters” was nominated for Best Picture along with Clint as Best Director) is just mind-blowing.
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Pale Rider
Warner Bros
Westerns have been kind to Clint. The 1985 film was the highest grossing western of the decade. Clint produced, directed, and starred in this one as a mysterious preacher who protects a village from a greedy mining company. Don’t mess with Clint.
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In The Line Of Fire
Warner Bros
We just don’t see thrillers like this anymore. Co-starring John Malkovich and Rene Russo, Clint both acted and directed this tense 1993 thriller that features great acting, a gripping story, and taut direction. Hollywood needs to get back to these.
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Sully
Warner Bros
Clint doesn’t appear onscreen in this one. He stays behind the camera and gives all the heavy lifting (and flying) to Tom Hanks. “Sully” tells the true story of the pilot who landed a commercial plane on the Hudson River. Clint’s quiet intensity plays with the structure of the story as well.