The best Clint Eastwood movies showcase why he is considered one of the most prolific and successful actors in film history. Now a 93-year-old filmmaker, Eastwood has been focusing on directing and is renowned for the speed at which he’s developing new movies at this stage of his life. While 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.
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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.
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15 In The Line Of Fire (1993)
Director Wolfgang Petersen
In the Line of Fire (1993) 0
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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.
Director Wolfgang Petersen Release Date July 8, 1993 Cast Clint Eastwood , John Malkovich , Rene Russo , Dylan McDermott , Gary Cole Runtime 128 Minutes
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 13
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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.
Director Brian G. Hutton Release Date March 12, 1969 Cast Richard Burton , Clint Eastwood , Mary Ure , Patrick Wymark , Michael Hordern , Donald Houston , Peter Barkworth , William Squire , Robert Beatty , Brook Williams , Neil McCarthy , Vincent Ball , Anton Diffring , Ferdy Mayne , Derren Nesbitt , Victor Beaumont , Ingrid Pitt Runtime 155 Minutes Expand
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 supporting 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 PGCrimeActionBiography
Escape From Alcatraz recounts the 1962 escape attempt from the infamous maximum-security prison by inmates Frank Morris and the Anglin brothers. The film stars Clint Eastwood as Morris and is directed by Don Siegel. This tense drama explores the planning and execution of the daring escape amidst the harsh conditions of Alcatraz, delving into the human spirit’s drive for freedom against seemingly insurmountable odds.
Director Don Siegel Release Date June 22, 1979 Cast Clint Eastwood , Patrick McGoohan , Roberts Blossom , Jack Thibeau , Fred Ward , Paul Benjamin , Larry Hankin , Bruce M. Fischer Runtime 112 Minutes
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 RWestern Where to Watch
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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.
Release Date April 6, 1973 Cast Clint Eastwood , Verna Bloom , Mariana Hill Runtime 105 Minutes
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 RCrimeComedyActionDrama
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.
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Director Michael Cimino Release Date May 23, 1974 Cast Clint Eastwood , Jeff Bridges , Geoffrey Lewis , Catherine Bach , Gary Busey , George Kennedy , Roy Jenson , Eugene Elman Runtime 115 Minutes
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 pg-13WesternDrama Where to Watch
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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.
Director Sergio Leone , Monte Hellman Release Date January 18, 1964 Cast Clint Eastwood , Marianne Koch , Gian Maria Volonte , Wolfgang Lukschy , Sieghardt Rupp , Joseph Egger Runtime 99minutes
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) PG-13CrimeDramaThriller
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.
Director Clint Eastwood Release Date November 24, 1993 Cast Kevin Costner , Clint Eastwood , Laura Dern , T.J. Lowther , Keith Szarabajka , Leo Burmester , Bruce McGill , Bradley Whitford , Ray McKinnon , Mary Alice , John M. Jackson , Wayne Dehart , Linda Hart , Cameron Finley , Marco Perella , Margaret Bowman , James Jeter Runtime 138 minutes Expand
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 PGWesternDramaAction Where to Watch
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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.
Director Clint Eastwood Release Date July 14, 1976 Cast Clint Eastwood , Chief Dan George , Sondra Locke , Bill McKinney , John Vernon , Paula Trueman Runtime 135 minutes
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 joining 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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7 Gran Torino (2008)
Directed By Clint Eastwood
Gran Torino 1
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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.
Release Date December 12, 2008 Director Clint Eastwood Cast Clint Eastwood , Christopher Carley , Bee Vang , Ahney Her , Brian Haley , Geraldine Hughes , Dreama Walker , Brian Howe , John Carroll Lynch , William Hill , Brooke Chia Thao , Chee Thao , Choua Kue , Scott Eastwood , Xia Soua Chang , Sonny Vue , Doua Moua , Greg Trzaskoma , John Johns , Davis Gloff , Thomas D. Mahard , Sarah Neubauer , Cory Hardrict , Nana Gbewonyo , Arthur Cartwright , Austin Douglas Smith , Conor Liam Callaghan , Michael E. Kurowski , Julia Ho , Maykao K. Lytongpao Runtime 116 Minutes Expand
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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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.
Release Date December 23, 1971 Director Don Siegel Cast Clint Eastwood , Harry Guardino , Reni Santoni , John Vernon , Andrew Robinson , John Larch Runtime 102 minutes
Following his success with Sergio Leone in the Spaghetti Western genre, Clint Eastwood’s stardom blossomed in America with his role as detective Harry Callahan in the 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.
5 The Bridges Of Madison County (1995)
Directed By Clint Eastwood
The Bridges of Madison County PG-13DramaRomance
The Bridges of Madison County is a romantic drama directed by Clint Eastwood, who also stars alongside Meryl Streep. The film tells the story of Francesca Johnson, a lonely Iowa housewife, who has a life-changing, four-day romance with Robert Kincaid, a traveling photographer visiting to photograph the county’s historic bridges. Set in 1965, the film explores themes of love, loss, and the roads not taken, as Francesca must choose between her family commitments and her heart’s desire.
Director Clint Eastwood Release Date June 2, 1995 Writers Richard LaGravenese , Robert James Waller Runtime 135 Minutes Cast Clint Eastwood , Meryl Streep , Annie Corley , Victor Slezak , Jim Haynie , Sarah Zahn , Christopher Kroon , Phyllis Lyons
A film that shows Clint Eastwood’s diverse abilities as a director, The Bridges of Madison County is one of his only ventures into the romance genre. Eastwood plays Robert Kincaid, a photographer hired to capture Madison County’s historic bridge landmarks. There, he meets Meryl Streep’s Francesca Johnson, a married woman whose family is away on a trip. The two have a passionate romance, with the film excellently exploring the emotional depth of their characters.
Clint Eastwood and Meryl Streep have remarkable chemistry, creating a great romantic drama with two film legends. It is the kind of sweeping romantic story that can be engrossing for audiences as well as heartbreaking, as it shows the many complications facing these middle-aged lovers. Streep was nominated for an Oscar for her role, but it also features one of Eastwood’s most subtle performances.
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4 For A Few Dollars More (1965)
Directed By Sergio Leone
For A Few Dollars More (1965) RDramaWestern
For A Few Dollars More is a classic Western featuring Clint Eastwood as a bounty hunter forming an uneasy alliance with a rival to capture a ruthless outlaw.
Director Sergio Leone Release Date May 10, 1967 Writers Sergio Leone , Fulvio Morsella , Luciano Vincenzoni Runtime 132 minutes
Clint Eastwood returns as the Man with No Name in For a Few Dollars More, reuniting with Leone for another unbelievable Western film. The film sees the Man hunting a vicious criminal known as El Indio and forms an unlikely partnership with Lee Van Cleef’s Douglas Mortimer, a rival bounty hunter. Though the two are driven by their own motives, their temporary working relationship is an exciting spectacle and the best aspect of the film.
Being dropped into the unique and somewhat surreal world of one of Sergio Leone’s Spaghetti Westerns is always a thrill.
Being dropped into the unique and somewhat surreal world of one of Sergio Leone’s Spaghetti Westerns is always a thrill. Though it is often an underrated entry in the trilogy, it stands comfortably with A Fistful of Dollars and The Good, the Bad and the Ugly as a truly great Western adventure. Eastwood helped turn bounty hunters into Western heroes, while Van Cleef steals many scenes going toe-to-toe with The Man with No Name.
3 Million Dollar Baby (2004)
Directed By Clint Eastwood
Million Dollar Baby PG-13DramaSport Where to Watch
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Million Dollar Baby is an Oscar-winning sports drama directed by Clint Eastwood and starring Eastwood, Hilary Swank, and Morgan Freeman. It follows Maggie Fitzgerald, a young female boxer, as she trains under the guidance of her trainer, Frankie Dunn, and tries to make it to the top.
Release Date December 15, 2004 Director Clint Eastwood Cast Hilary Swank , Mike Colter , Jay Baruchel , Clint Eastwood , Morgan Freeman Runtime 132 minutes
Clint Eastwood has won four Oscars in his career, with Million Dollar Baby earning him two for Best Picture and Best Director. The sports film sees Eastwood as Frankie Dunn, a boxing trainer who reluctantly takes on his first female fighter (Hilary Swank). Her enthusiasm and respect for him as a coach allow them to grow a bond that makes him confront the mistakes of his past and allows her the confidence to be a competitor.
Eastwood’s directing and performance are some of his best, allowing the film to be a critical and commercial success. Million Dollar Baby is a powerful story that transcends the norms of the sports genre. It turns into a beautiful father-daughter story with a heartbreaking conclusion which is delivered beautifully by the whole team. Swank won the Oscar for Best Actress while Eastwood scored his first Oscar nomination for acting.
2 Unforgiven (1992)
Directed By Clint Eastwood
Unforgiven RWesternDrama Where to Watch
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Unforgiven, directed by and starring Clint Eastwood, is a Western that delves into the myths of the American West. The film follows William Munny, a retired and widowed outlaw, who takes on one last job with his old partner and a young gunslinger. They aim to avenge a disfigured prostitute in a corrupt town controlled by a brutal sheriff. The film explores themes of redemption, the brutal realities of frontier justice, and the consequences of violence.
Director Clint Eastwood Release Date August 7, 1992 Cast Clint Eastwood , Gene Hackman , Morgan Freeman , Richard Harris , Jaimz Woolvett , Saul Rubinek , Frances Fisher Runtime 130 Mins
Clint Eastwood’s other two Academy Awards were won for Unforgiven, which also won Best Picture and Best Director. The 1992 classic is Clint Eastwood’s most important contribution to the Western genre as a director, setting a gold standard for the bleak, revisionist Westerns of recent decades. Eastwood plays a former outlaw who has settled into a family life only to take a final job after being hired by a group of sex workers to kill that man who scarred one of them.
As his last true Western in Clint Eastwood’s historic career,
Unforgiven
deconstructs the mythology of the Western film genre
As his last true Western in Clint Eastwood’s historic career, Unforgiven deconstructs the mythology of the Western film genre, following morally complex characters who are far from heroes. The film explores violent, cowardly, morally complex men, giving a truer taste of what the Wild West looked like. It is a dark and brilliant movie featuring some of Eastwood’s best work behind and in front of the camera.
1 The Good, The Bad, And The Ugly (1966)
Directed By Sergio Leone
The Good the Bad and the Ugly RWesternAdventureDrama
The Good, the Bad and the Ugly is a Spaghetti Western directed by Sergio Leone, scored by Ennio Morricone, and starring Clint Eastwood, Lee Van Cleef, and Eli Wallach as three gunslingers who compete for a cache of Confederate gold during the American Civil War. The 1966 film is regarded as one of the greatest Westerns of all time.
Release Date December 29, 1967 Director Sergio Leone Cast Aldo Giuffrè , Eli Wallach , Clint Eastwood , Lee Van Cleef , Luigi Pistilli Runtime 178 minutes
The Good, the Bad, and the Ugly is not only Clint Eastwood’s best movie, but it’s also one of the best movies of all time. It’s the definitive epic Western, concluding The Dollars Trilogy with its largest narrative. The movie follows three dangerous and deadly men in the Old West during the Civil War who converge on a journey to locate a buried treasure.
Clint Eastwood, Lee Van Cleef, and Eli Wallach deliver iconic performances, and Ennio Morricone’s “The Ecstasy of Gold” theme became one of the most recognizable film scores ever created. There are so many iconic moments, with the climactic standoff scene in contention as the greatest sequence of filmmaking in history. The Good, the Bad, and the Ugly should be considered essential viewing for everyone, but particularly for those who love Clint Eastwood’s movies.
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