The best Clint Eastwood has directed some great films dating back to the 1970s, he's best known for his acting roles, rising to fame in the 1960s as a charismatic, tough leading man in movies like The Good, the Bad, and the Ugly and later the Dirty Harry series.

Eastwood's acting is recognized for being synonymous with the Western genre, or more specifically, the Spaghetti Western and revisionist Western subgenres. Sergio Leone's Man with No Name trilogy is iconic, and Eastwood continued to develop the genre with films like The Outlaw Josey Wales and Unforgiven, which he directed and starred in. Clint Eastwood has been in some of the best Western movies ever made, but he's made sure to expand his career to other avenues with movies like Million Dollar Baby and A Perfect World.

15 In The Line Of Fire (1993)

Director Wolfgang Petersen

In the Line of Fire (1993) - Poster - Clint Eastwood

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In the Line of Fire
Release Date
July 8, 1993
Runtime
128 Minutes
Director
Wolfgang Petersen

WHERE TO WATCH

Streaming

In the Line of Fire is a thriller film where a veteran Secret Service agent, Frank Horrigan, played by Clint Eastwood, is haunted by his failure to protect President John F. Kennedy in 1963. Decades later, he is assigned to investigate a mysterious threat on the life of the current US President, while a psychopathic assassin, Mitch Leary, played by John Malkovich, begins to stalk and taunt him.

As Clint Eastwood got older in Hollywood, he began to embrace roles that suited his age but also allowed him to continue playing the tough and cool action hero. In the Line of Fire is one of the best examples from the 1990s with Eastwood playing Secret Service agent Frank Horrigan, one of the men on duty when JFK was assassinated. Horrigan comes out of retirement and returns to his post when there is a new threat to the life of the current president.

However, the best aspect of the movie is John Malkovich's villainous turn as the would-be assassin.

In the Line of Fire is a taught and intense thriller with a terrific pace. Eastwood is great in the lead role, playing a hero who is past his prime yet determined to prove that he is still the best man for the job. However, the best aspect of the movie is John Malkovich's villainous turn as the would-be assassin. He is creepy yet captivating as he becomes fascinated with Horrigan. Malkovich earned a rare Oscar nomination in an action movie.

14 Where Eagles Dare (1968)

Director Brian G. Hutton

Where Eagles Dare - Poster

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Where Eagles Dare
Release Date
March 12, 1969
Runtime
155 Minutes
Director
Brian G. Hutton

WHERE TO WATCH

Streaming

Where Eagles Dare is a gripping action thriller set during World War II, following a group of Allied commandos on a daring mission to rescue an American general held captive in a mountaintop fortress. Battling treacherous weather and enemy forces, the team must navigate deception and betrayal in a high-stakes operation. The film blends intense combat sequences with strategic espionage, delivering a suspenseful and engaging wartime adventure.

Clint Eastwood has starred in a number of war movies throughout his career but the best was the World War II adventure, Where Eagles Dare. Based on the novel Alistair MacLean, the movie stars Richard Burton as a British officer who leads a team into Bavaria to a German mountain base in order to rescue a captured American intelligence officer. Eastwood plays the lone American soldier who is recruited to the team.

It is a lot of fun seeing Eastwood in a ing role in a movie like this. However, his star power shines through in the smaller role, bringing charisma and humor to the heroic role. The adventure unfolds with great action and intense sequences on the mountainside location, including the thrilling climax in cable cars. It is a great mix of fun and action in the vein of the war adventure movies of the period, like The Dirty Dozen and The Great Escape.

13 Escape From Alcatraz (1979)

Director Don Siegel

Escape From Alcatraz - Poster - Clint Eastwood

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Escape from Alcatraz
PG
Crime
Action
Biography
Release Date
June 22, 1979
Runtime
112 Minutes
Director
Don Siegel
  • Headshot Of Clint Eastwood In The AFI Fest 2011
    Frank Morris
  • Cast Placeholder Image
    Patrick McGoohan
    Warden
  • Cast Placeholder Image
    Roberts Blossom
    Doc
  • Cast Placeholder Image
    Jack Thibeau
    Clarence Anglin

WHERE TO WATCH

Streaming

Escape From Alcatraz is a gripping thriller that chronicles the ingenious escape of three prisoners from the formidable Alcatraz Island prison. Set against the backdrop of the infamous penitentiary, the film portrays the meticulous planning and execution of their daring breakout. Led by inmate Frank Morris, the plot delves into the challenges faced in orchestrating one of the most famous prison escapes in history, highlighting themes of determination and resilience.

Escape from Alcatraz marks the fifth and final movie Clint Eastwood made with Don Siegel, bringing to an end one of the most important collaborations of the actor's career. As it happens, it is a terrific final note for the duo to end on. Escape from Alcatraz is one of the best prison escape movies with Eastwood playing Frank Morris, a career criminal with a penchant for escaping from custody. He is transferred to Alcatraz, one of the most notorious and seemingly inescapable prisons in America. There, he devises his latest plan for breaking out.

He had already proven many times before that he has plenty of screen presence without saying a word and he proves it once again here

The simple story is beneficial for the movie and for Eastwood's performance. He had already proven many times before that he has plenty of screen presence without saying a word and he proves it once again here. The thrill of the movie is seeing the meticulous planning that goes into Frank's escape and the anticipation of seeing it set in motion.

12 High Plains Drifter (1973)

Directed By Clint Eastwood

High Plains Drifter Showing Clint Eastwood Holding a Gun and a Whip

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High Plains Drifter
Release Date
April 6, 1973
Runtime
105 Minutes
Director
Clint Eastwood

WHERE TO WATCH

Streaming

High Plains Drifter, directed by Clint Eastwood, follows a mysterious stranger who rides into the small town of Lago and is hired to protect it from outlaws. As he assumes control, his presence reveals the town's dark secrets. Eastwood stars in this Western that explores themes of vengeance and morality. The film blends traditional Western elements with a haunting atmosphere and complex character dynamics.

Part of the reason Clint Eastwood became a Western legend was the way he was willing to play around with the genre. He became a star at a time when the standard John Wayne Western movies were starting to grow a little dull for audiences. Eastwood was the perfect antidote for this and High Plains Drifter is a prime example. The darker Western movie stars Eastwood as a mysterious drifter who comes to a mining town and begins delivering his brutal band of justice to the corrupt locals.

The result is a terrific Eastwood performance that plays against conventions and an even better display of his directing skills.

The movie boldly challenges the idea of the quintessential Western hero, with Eastwood playing more of an antihero with a lot less likable qualities than these roles typically have. There is also a hint of a supernatural aspect to the movie that helps it to stand out even more. The result is a terrific Eastwood performance that plays against conventions and an even better display of his directing skills.

11 Thunderbolt And Lightfoot (1974)

Directed By Michael Cimino

Thunderbolt and Lightfoot - Poster

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Thunderbolt and Lightfoot
Release Date
May 23, 1974
Runtime
115 Minutes
Director
Michael Cimino

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Thunderbolt and Lightfoot is a crime drama directed by Michael Cimino, featuring Clint Eastwood as a seasoned bank robber named Thunderbolt and Jeff Bridges as the energetic and charismatic drifter Lightfoot. Set in the American West, the film follows their partnership as they plan an ambitious heist while evading their vengeful former associates. The movie marks Cimino's directorial debut and is celebrated for its strong performances and blend of action and humor.

It is not often Clint Eastwood shares the spotlight with another actor, but the buddy action movie Thunderbolt and Lightfoot showcases just how much fun it can be with the right partner. Eastwood plays Thunderbolt, a criminal looking to pull off his next big job when he crosses paths with a fun-loving, reckless, but charismatic young man named Lightfoot (Jeff Bridges). The two form a quick bond as they set out to pull off the score.

Bridges' gets the flashier role to be sure with him scoring an Oscar nomination. However, the chemistry between the two lead actors is really what sells the movie. The quickness with which these outlaws become best friends and the bond they share is charming, with a surprising sadness to the ending. However, the movie is just a fun comedy caper from beginning to end with some big laughs that still hold up decades later.

10 A Fistful Of Dollars (1964)

Directed By Sergio Leone

a fistful of dollars

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A Fistful of Dollars
Release Date
January 18, 1964
Runtime
99minutes
Director
Sergio Leone, Monte Hellman

WHERE TO WATCH

A Fistful of Dollars is a spaghetti Western film from director Sergio Leone starring Clint Eastwood. A Fistful of Dollars is notable for being Clint Eastwood's big break in Hollywood and also for being the beginning of the "Dollars Trilogy." The film was followed by For a Few Dollars More in 1965 and The Good, The Bad and the Ugly in 1966.

With the iconic success of The Good, the Bad, and the Ugly, many have forgotten that it's actually the third installment of a trilogy of films. The Dollars Trilogy is a series of Spaghetti Westerns directed by the legendary Sergio Leone, though all three can be viewed as standalone movies with no connected plots. The connecting point in all three is Eastwood's Man with No Name, one of the best Western movie protagonists ever.

Eastwood is consistently fantastic as the cool, ambiguous, anti-hero character in all three movies in The Dollars Trilogy

A Fistful of Dollars marks the first movie in the trilogy and follows the Man as he manipulates two rival gangs into warring against each other. As the premise suggests, it is a loose adaptation of Akira Kurosawa's Yojimbo, but brought to life with Leone's own iconic filmmaking style, becoming a unique and special adventure. Eastwood is consistently fantastic as the cool, ambiguous, anti-hero character in all three movies in The Dollars Trilogy, and Ennio Morricone's score is a highlight of the first film.

9 A Perfect World (1993)

Directed By Clint Eastwood

A Perfect World (1993)

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A Perfect World
Release Date
November 24, 1993
Runtime
138 minutes
Director
Clint Eastwood

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A Perfect World stars Kevin Costner as an escaped convict who kidnaps a young boy. As the two form an unlikely bond during their run from the law.

In A Perfect World, Western legend Clint Eastwood directs and co-stars with another Western legend, Kevin Costner. The film is a crime thriller where Costner plays an escaped prisoner named Butch, who kidnaps a young boy. Butch and the boy form an unlikely bond as they go on the run together, but Eastwood's Red Garnett, a Texas Ranger leading the pursuit, must bring them both in.

The film explores a complex relationship, with Costner giving one of his most underrated performances as this flawed yet charming character who develops a bond with his young hostage. Eastwood is terrific in his role, while many critics praised it as one of his finest directing achievements as well. It is a gritty crime story with some dark and haunting aspects to it, all balanced wonderfully by Eastwood and elevated by the performances.

8 The Outlaw Josey Wales (1976)

Directed By Clint Eastwood

The Outlaw Josey Wales - Poster

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The Outlaw Josey Wales
Release Date
July 14, 1976
Runtime
135 minutes
Director
Clint Eastwood

WHERE TO WATCH

Streaming

The Outlaw Josey Wales is a 1976 Western film directed by and starring Clint Eastwood. Set during and after the American Civil War, the film follows Josey Wales, a Missouri farmer seeking revenge for the murder of his family by Union soldiers. As he becomes an outlaw, Wales forms an unlikely band of outcasts and confronts various adversaries while struggling with his quest for vengeance and a chance at redemption.

Clint Eastwood had a feud with John Wayne over the years, with Wayne taking exception to the changes Eastwood's movies were making to the Western genre. In particular, Eastwood seemed more interested in challenging movies with flawed protagonists rather than picture-perfect heroes. One of Eastwood's earliest directed films, The Outlaw Josey Wales, is a great example of that.

The fact that Eastwood was also able to deliver one of his own best Western movies as a director showed he had an impressive filmmaking career ahead of him.

Wales is a complex, violent character who seeks revenge on Union soldiers during the Civil War who murdered his family. Initially ing the Confederate Army to carry out his vengeance, he refuses to back down after the war ends, taking the matter into his own hands. The Outlaw Josey Wales is a nuanced, sprawling Western that explores the post-Civil War era, with Eastwood giving a powerful performance. The fact that Eastwood was also able to deliver one of his own best Western movies as a director showed he had an impressive filmmaking career ahead of him.

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The 9 Clint Eastwood Movies That Defined His Career

While Clint Eastwood has seen fame for both starring and directing many films, 8 titles that stand out as being defining moments in his career.

7 Gran Torino (2008)

Directed By Clint Eastwood

Gran Torino Movie Poster

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Gran Torino
10/10
Release Date
December 12, 2008
Runtime
116 Minutes
Director
Clint Eastwood

WHERE TO WATCH

Gran Torino stars Clint Eastwood as Walt Kowalski, a Korean War veteran and retired auto worker who forms an unexpected bond with his Hmong neighbors. Set in a Detroit neighborhood, the film explores themes of racial tension, cultural exchange, and redemption. Directed by Eastwood, it delves into the complexities of aging, prejudice, and the search for connection in a changing world.

Gran Torino is one of Clint Eastwood's most successful 21st-century movies, following a Korean War veteran named Walt Kowalski. Kowalski is an angry, bigoted man who forms an unlikely bond with a local Hmong teenager named Thao. He becomes an unlikely hero as he confronts the gang violence in his neighborhood. The film earned praise for its thematic exploration of racism and redemption in contemporary America as Kowalski attempts to overcome his prejudices.

While not a particularly deep movie, it was a lot of fun seeing Eastwood back in his tough-guy mode, especially in a role like Walt that made full use of his age. There were even some fans who saw Gran Torino as an unofficial Dirty Harry sequel, imagining what the legendary cop's life was like after retiring from the police force. However, on its own, it remains a thrilling yet grounded and intimate action movie that shows Eastwood can still be intimidating.

6 Dirty Harry (1971)

Directed By Don Siegel

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Dirty Harry
10/10
Release Date
December 23, 1971
Runtime
102 minutes
Director
Don Siegel

WHERE TO WATCH

Clint Eastwood stars in the western Dirty Harry as a no-nonsense San Francisco cop who takes the law into his own hands in pursuit of a serial killer, Scorpio. Directed by Don Siegel and featuring a memorable score by Lalo Schifrin, the film is known for its iconic catchphrases and intense action scenes, and has influenced countless films and TV shows in the years since its release.

Following his success with Sergio Leone in the Spaghetti Western genre, Clint Eastwood's stardom blossomed in America with his role as detective Dirty Harry film series. Dirty Harry is the first of five movies that sees Callahan in pursuit of a psychopathic sniper called the Scorpio Killer, inspired by the real-world case of the Zodiac Killer.

Though he was a controversial movie hero throughout the entire franchise, Eastwood helped to sell the roughness of the character with charm.

The film's timeliness in capturing the intrigue of a major cultural event and its gritty portrayal of urban crime allowed it to become a cultural phenomenon. The tough cop character of Dirty Harry has been a monumental influence in crime thriller films since. Though he was a controversial movie hero throughout the entire franchise, Eastwood helped to sell the roughness of the character with charm. Even the infamous "Well do ya, punk" scene is delivered with Eastwood's iconic smirk.