Clint Eastwood's Top 10 Most Essential Movies, Ranked

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Clint Eastwood is more than just the "Man with No Name." The award-winning star has performed in and directed some of the best movies ever made. Originally a Western star, Eastwood specializes in all things action and drama — anything that makes audiences sit on the edge of their seats.

In anticipation of his upcoming Western film Cry Macho, fans have been turning to Eastwood’s long-running film career to tide them over. From The Bridges of Madison County and Dirty Harry to Million Dollar Baby and Mystic River, Eastwood has plenty of classics under his belt — but which films are his best? According to IMDb’s rankings, these 10 films are required viewing for any Eastwood fan.

10. Dirty Harry (1971)

The 1971 action film Dirty Harry was so popular that it resulted in four consecutive films: Magnum Force (1973), The Enforcer (1976), Sudden Impact (1983) and The Dead Pool (1988). Eastwood starred in all five films, playing the San Francisco Police Department Homicide Division's Inspector "Dirty" Harry Callahan.

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In the films, Dirty Harry is known for his (often) violent, nontraditional methods of seeking out criminals. In addition to hunting serial killers, Eastwood’s character speaks quite bluntly, delivering iconic lines like, "You’ve got to ask yourself a question: ‘Do I feel lucky?’ Well, do ya, punk?"

9. The Outlaw Josey Wales (1976)

Many of Eastwood’s best films are ones that also saw him in the director’s chair. The 1976 Western war film The Outlaw Josey Wales is one of those many films that sees the actor helming the film in more ways than one.

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Eastwood stars as the title character, a Confederate soldier set on seeking revenge against the Union after his wife and child are brutally murdered by Captain Terrill (Bill McKinney). Critics praised Eastwood’s performance as a man who believably refuses to surrender — no matter the cost.

8. Mystic River (2003)

One of Eastwood’s best directing projects is the 2003 mystery-thriller Mystic River. The movie focuses on ex-conman Jimmy Marcus (Sean Penn), whose daughter (Emmy Rossum) is murdered. The catch? His childhood friends were involved with the murder.

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Understandably, Jimmy wants to know what happened to his daughter, so he teams up with Dave (Tim Robbins), the man who saw her last, and Sean (Kevin Bacon), a homicide detective assigned to the case. But can Jimmy trust anyone? Watch this six-time Academy Award-nominated film to find out.

7. Letters from Iwo Jima (2006)

In 2006, Eastwood directed the World War II drama, Letters from Iwo Jima and, once again, he was praised for his work. In fact, he received one of his several Academy Award nominations for Best Director due to this film’s success.

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The film showcases the stories of the Japanese troops who died on Iwo Jima during the war. This includes a baker, Saigo (Kazunari Ninomiya); an Olympic champion, Baron Nishi (Tsuyoshi Ihara); and a soldier, Shimizu (Ryo Kase). Their leader, Lieutenant General Tadamichi Kuribayashi (Ken Watanabe), understands that their chance of survival is grim, but still tries his best to protect his troops.

6. A Fistful of Dollars (1964)

In the 1960s, Eastwood starred in Rawhide, a western drama television series, but he also made a name for himself on the silver screen, playing the "Man with No Name" in a now-classic trilogy. The first of the films in that trilogy? The 1964 hit A Fistful of Dollars.

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Eastwood’s nameless character arrives in San Miguel, Mexico during a power struggle between the three Rojo brothers (Antonio Prieto, Benny Reeves and Sieghardt Rupp) and Sheriff John Baxter (Wolfgang Lukschy). Our protagonist gets involved in the action, ultimately selling false information to both sides of the scuffle.

5. Gran Torino (2008)

In 2008, Eastwood both directed Gran Torino, a thriller-drama that focuses on the relationship between an angry, recently widowed Korean War vet, Walt Kowalski (Eastwood), and teenager Thao Vang Lor (Bee Vang). When Thao is pressured by his cousin to steal Walt’s 1972 Ford Gran Torino, Walt thwarts the theft and realizes he and Thao have a lot in common.

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While the film features a large Hmong American cast and, as reflected in its IMDb ranking, received a great deal of critical praise, Hmong people, including Vang, found Gran Torino’s depiction of Hmong Americans offensive and, often, inaccurate. "[T]he producers preferred whichever Hmong ‘cultural consultant’ had the most amenable take on the matter [even if actors objected] and would lend credence to whatever Hollywood stereotypes the film wanted to convey," Vang said in an interview. "I reminded my critics that this was a white production, that our presence as actors did not amount to control of our images."

4. Million Dollar Baby (2004)

Without a doubt, the sports drama Million Dollar Baby (2004) is one of Eastwood’s best projects. It tells the story of Frankie Dunn (Eastwood), a veteran Los Angeles boxing trainer who is hesitant about everyone he meets. The one exception? Dunn's close friend, Eddie "Scrap Iron" Dupris (Morgan Freeman).

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Things take a real turn when Maggie Fitzgerald (Hilary Swank) wants to train with Frankie — and, although he has his reservations, Frankie agrees to work with her. In typical curmudgeon-meets-dedicated-young-person fashion, Maggie and Frankie form a close bond. Regarded as a masterpiece by critics, Million Dollar Baby received four Oscars, including Best Picture, Best Director, Best Actress (Swank) and Best Supporting Actor (Freeman).

3. Unforgiven (1992)

Many movie fans regard the 1992’s Unforgiven as one of the best movies ever made. The film tells the story of sex worker Delilah Fitzgerald (Anna Thomson), who is injured by a group of cowboys in Big Whiskey, Wyoming. Hoping to get revenge on the cowboys, Delilah’s coworkers offer up a reward — and, in true Western fashion, aging bandit William Munny (Eastwood) takes on the job.

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Notably, this was the film that put Eastwood on the map as a big-time Hollywood director. In fact, Unforgiven received near-perfect reviews and, when awards season came around, it earned four Academy Awards, including Best Picture and Best Director.

2. For a Few Dollars More (1965)

The 1965 Western For a Few Dollars More is the second film in the Dollars Trilogy. Reprising his role as the "Man with No Name," Eastwood is a bounty hunter looking to collect a prize for finding the outlaw El Indio (Gian Maria Volonte) and his gang.

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Although Eastwood’s character works with Colonel Douglas Mortimer (Lee Van Cleef), the two might actually be enemies themselves. Still, circumstance proves to be a strange thing. Sure, For a Few Dollars More might be the least popular film in the trilogy, but it’s still a genre-defining classic.

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

Directed by the legendary Sergio Leone, this epic Spaghetti Western has quite the lasting legacy. In fact, this final film in the Dollars Trilogy is often touted as one of the best Westerns ever made. So, what’s The Good, the Bad and the Ugly (1966) about?

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In this installment, Eastwood’s iconic "Man with No Name," a.k.a. "the Good," competes with two other gunslingers — Mexican outlaw Tuco (Eli Wallach), a.k.a. ""the Ugly," and Lee Van Cleef’s character, a.k.a. "the Bad" — to find a fortune in a buried cache of Confederate gold. With distinctive cinematography and stylistic gunfights, Eastwood’s best is also a must-watch for all cinephiles.

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