Clint Eastwood’s Most Iconic Movie Moments, Ranked

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Over his six-decade career, both acting and directing (and as Mayor), screen legend Clint Eastwood has made quite an impact. The steely-eyed, gravelly-voiced actor pretty much is the definition of the Spaghetti Western. He made the .44 magnum one badass weapon, and when it all looked lost for the Western, he brought it back in vogue.

Not only is Clint Eastwood an iconic actor, but he has been part of numerous iconic moments on the big screen. Here are his top 8.

Clint Eastwood’s Most Iconic Movie Moments

8. A Fistful of Dollars (1964)

Who can forget Clint Eastwood’s entrance as “The Man with No Name” in the first of the “Dollars Trilogy”, A Fistful of Dollars? Walking through a cloud of smoke, wearing that distinctive poncho, stoic and ready to cause trouble, it was a career-making entrance. Eastwood would team up with director Sergio Leone two more times in classic fashion as The Man with No Name.

7. Any Which Way You Can (1980)

After putting his stamp on the non-conforming cop with Harry Callahan, Clint Eastwood decided to try his hand at comedy. So, in 1978 he starred in Every Which Way But Loose as Philo Beddoe, a rough-and-tumble bare-knuckle fighter who hung out with Clyde, his pet orangutan.

The film was a modest hit for Eastwood, enough so that a sequel was warranted. This came in 1980 with Any Which Way You Can and saw Beddoe and Clyde take on their old foes, The Black Widows. It produced one of Eastwood’s most iconic movie moments – “Right turn, Clyde.”

6. High Plains Drifter (1973)

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In High Plains Drifter, Clint Eastwood is the Stranger, another man with no name, who comes to the small town of Lago to mete out his own sense of justice. The townsfolks, looking for protection against three outlaws who are on their way to take care of some unfinished business, hire the Stranger to help against the outlaws.

Justice is what The Stranger serves up as he single-handedly transforms the town of Lago into a place of revenge and justice, leaving a most haunting impression. High Plains Drifter is the first Western that Eastwood starred in and directed.

5. The Outlaw Josey Wales (1976)

You can’t say he didn’t try. As Josey Wales, Clint Eastwood plays an outlaw with a deadly gun being pursued by Union soldiers. One of the most iconic moments in the film is when a bounty hunter finds Josey inside an outpost, threatening to take him in. Josey steps forward from the shadows, telling the man, “Dying ain’t much of a living, boy,” to which the man retreats. Unfortunately for the man, he returns with a sense of pride. Bad move.

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4. Unforgiven (1992)

The entire film was a slow build to Clint Eastwood’s William Munny finally meeting up with Little Bill Daggett (Gene Hackman) in their violent saloon showdown. Munny is out for revenge after Little Bill and his crew killed Munny’s best friend Ned (Morgan Freeman) and left him out front of the saloon for all to see.

The saloon gunfight is classic Eastwood, but it’s his final confrontation with Little Bill that is so iconic as he delivers the line, “Deserve’s got nothin’ to do with it.”

3. Sudden Impact (1971)

One of Clint Eastwood’s most iconic and enduring characters has to be the .44 magnum-wielding cop, Dirty Harry Callahan. Eastwood starred five times as Callahan, each with a catchphrase that traveled across the country for all to use. In the opening scene of Sudden Impact, Eastwood’s fourth time as Dirty Harry, he delivered one of the best – “Go ahead, make my day.”

2. The Good, the Bad, and the Ugly (1966)

The Good, the Bad, and the Ugly was the third film in Sergio Leone’s Dollars Trilogy and is considered to be the best of the bunch. Clint Eastwood again starred as The Man With No Name, alongside Lee Van Cleef and Eli Wallach. The most iconic moment comes in the three-way showdown between No Name, Angel Eyes (Van Cleef), and Tuco (Wallach). The scene is filled with tension and intensity.

1. Dirty Harry (1971)

This was the film that created a legend. Clint Eastwood began his Harry Callahan career with 1971’s Dirty Harry and right from the start, he proved to be the right man for the job. After a shootout on the streets of San Francisco stopping a bank robbery, Eastwood makes his way over to the only surviving bank robber. The man, lying in a pool of his own blood, has his hand near his shotgun, carefully thinking about reaching for it.

It is then that Inspector Harry Callahan turns into Dirty Harry, delivering his famous speech. “I know what you’re thinking, ‘Did he fire six shots or only five?’ Well, to tell you the truth, in all this excitement, I’ve kinda lost track myself. But being this is a .44 magnum, the most powerful handgun in the world and can blow your head clean off,  you’ve gotta ask yourself one question: ‘Do I feel lucky?’ Well, do ya, punk?”

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