10 Most Rewatchable Clint Eastwood Movies, Ranked

It’s hard to overstate the incredible influence that Clint Eastwood has had on the film industry over the course of his career. Ever since the emergence of the “spaghetti western” genre in the 1960s thanks to Sergio Leone’s A Fistful of Dollars, Eastwood has become known for playing tough, cool anti-heroes in action and western films. While his leading roles in “The Man With No Name” trilogy and performance as Harry Calhaun are certainly well known, Eastwood’s directorial efforts have earned just as much acclaim.

Despite being known as one of the most iconic western actors ever, Eastwood has found success in many different genres. Recent years have seen him telling true stories like Richard Jewell, but Eastwood has also experimented with science fiction, horror, musical, comedy, and family films. With his last directed film Juror #2 set to hit theaters later this year, it’s a better time than ever to celebrate the work of one of the entertainment industry’s living legends. Here are the ten most rewatchable Clint Eastwood movies, ranked.

10 ‘Escape from Alcatraz’ (1979)

Directed by Don Siegel

While it’s a subgenre that’s been done countless times, Escape From Alcatraz is one of the greatest “prison break” movies ever made. Eastwood has already worked with director Don Siegel, and turned in one of his greatest performances as Frank Morris, a convict who made connections within the world’s most dangerous prison and led a daring escape. Eastwood perfectly captures the grizzled intelligence of a lifelong criminal who has been hardened by the world; it’s due to his brutality that the film is as gripping as it is.

Eastwood has played his fair share of anti-heroes, but Escape From Alcatraz is an incendiary indictment of the American justice system that exposes the flaws within prison infrastructure. The entertainment value of the escape sequences and the commentary on abuse of authority make Escape From Alcatraz worth revisiting by modern film buffs.

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9 ‘Gran Torino’ (2008)

Directed by Clint Eastwood

Although he’s starred in a number of films that he also directed, Eastwood gave one of his most sincere and emotional performances in Gran Torino. He stars as a veteran who forms a unique friendship with a young man in his community, and becomes involved in an effort to stop gang violence. Eastwood showed more sensitivity in playing a man capable of having his mind changed; in addition to giving generous space to his younger co-star, Eastwood also contributed the titular song “Gran Torino” to the film’s soundtrack.

It may be one of his slower movies, but Gran Torino allowed Eastwood to address serious issues like race relations and gang violence. It’s impressive that a filmmaker of Eastwood’s experience continues to push for greater representation in the industry, and Gran Torino certainly stands as one of his more underrated efforts.

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8 ‘In the Line of Fire’ (1993)

Directed by Wolfgang Peterson

Conspiracy films peaked in the American entertainment industry in the 1970s due to the scandals of the Richard Nixon Presidential administration, and Wolfgang Peterson’s In the Line of Fire served as a throwback to a classical age of political thrillers. Eastwood stars as a disgruntled secret service agent who feels guilty for failing to protect President John F. Kennedy in 1963; however, he is forced to redeem himself when a vengeful assassin (John Malkovich) sets his sights on the new President.

In the Line of Fire perfectly merges action and mystery to create a non stop, highly rewatchable thrill ride, and gives Eastwood more than a few opportunities to show his physical prowess. While Eastwood is perfectly cast as a grizzled law enforcement officer, Malkovich’s scene stealing villainous performance earned him a well deserved Academy Award nomination for Best Supporting Actor.

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7 ‘High Plains Drifter’ (1973)

Directed by Clint Eastwood

High Plains Drifter is arguably the most important film of Eastwood’s career, as it was the first western that he directed. While Eastwood’s directorial debut Play Misty For Me was an impressive first feature, High Plains Drifter allowed him to utilize the western skills that he’d adopted through his work with Leone on the “Dollars trilogy.” High Plains Drifter merged the “spaghetti western” sensibilities with a darker, revisionist style of filmmaking that reflected the maturation of American genre movies in the 1970s.

High Plains Drifter is worth rewatching for its significant influence on the rest of Eastwood’s career, as stylistically he would attempt to replicate it several times. While his later work on Pale Rider and The Outlaw Josey Wales were undoubtedly impressive, Eastwood created a chilling atmosphere in High Plains Drifter that set the precedent for his later work.

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6 ‘Million Dollar Baby’ (2004)

Directed by Clint Eastwood

The second film to win him both the Academy Award for Best Picture and Best Director, Million Dollar Babyis one of the most emotional sports movies ever made. Eastwood stars as a lifelong boxing coach who reluctantly agrees to begin training an energetic young protege (Hillary Swank) alongside his lifelong best friend (Morgan Freeman). The trio of powerful performances help elevate Million Dollar Baby above other inspirational boxing dramas; Eastwood deserves respect for avoiding cliches and pushing for more authenticity.

Although it ends on a moment so tragic that it disturbed many viewers, Million Dollar Baby is worth rewatching because of the emotional rollercoaster it takes its audience on. Despite its downbeat ending, Million Dollar Baby celebrates the perseverance of athletes who rise from nothing to find great success. It’s reflective of the positive messaging that is relevant within many of Eastwood’s finest works.

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5 ‘Dirty Harry’ (1971)

Directed by Don Siegel

Eastwood may have never played a character as quotable as the protagonist of the Dirty Harry franchise, as the phrase “do I feel lucky?” is one that his fans enjoy reciting. While each entry in the five film franchise is entertaining in its own right, the original Dirty Harry was highly influential in how it merged thriller and action movie sensibilities. While pre-1970s action films tended to be more superficial, Dirty Harry opted to take a gritty approach to gun violence and the threat of domestic terrorism.

Harry Calahan is certainly one of Eastwood’s coolest characters, but Dirty Harry doesn’t just coast on his charisma. Siegel creates a tightly paced, anxiety inducing thrill ride that features a terrific villainous performance from Andrew Robinson. It’s impressive that over five decades after its initial release, Dirty Harry is still a highly rewatchable classic.

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4 ‘A Perfect World’ (1993)

Directed by Clint Eastwood

Perhaps the most underrated movie of his career, A Perfect World allowed Eastwood to reinvent the neo-western genre by telling a getaway crime story. Eastwood actually took the supporting role of the Texas Ranger Red Garnett, who is in pursuit of the escaped criminal Butch (Kevin Costner). The film questions both character’s intentionality as Butch becomes a mentor to a small boy, and begins to reflect upon what his life’s work has amounted to.

He’s best known for action films, but A Perfect World showed that Eastwood was capable of telling more sincere and emotional stories. The film’s strongest moments are often quiet interactions between characters that show a more sensitive side of masculinity. In addition to the great supporting work from Keith Szarabajka and Laura Dern, A Perfect World is worth revisiting to see the dexterity of Eastwood’s directorial efforts.

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3 ‘Mystic River’ (2003)

Directed by Clint Eastwood

A gripping murder mystery about the perils of abuse and reflect, Mystic River is a haunting crime thriller that explores the true darkness of human nature. Eastwood paints a stirring portrait of life in Boston, where a traumatic childhood event causes three friends to turn on each other later in life. The murder of a teenage girl (Emmy Rossum) inspires the community to break down into anarchy; Eastwood asks existential questions about revenge and justice that linger long after the credits have rolled.

Although it wasn’t a film Eastwood personally appeared in, Mystic River is worth rewatching for its incredible performances. Sean Penn gave the performance of his career as a vengeful father hell bent on finding someone to blame for his daughter’s death, regardless of their guilt; Tim Robbins is also memorable as a victim of abuse who reaches his breaking point.

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2 ‘The Good, The Bad, and the Ugly’ (1966)

Directed by Sergio Leone

Both A Fistful of Dollars and For A Few Dollars More are classics in their own right, but The Good, The Bad, and the Ugly was the crowning achievement of Leone’s “The Man with No Name” trilogy. Eastwood’s performance as the enigmatic drifter “Blondie” was the perfect protagonist for this epic western; it’s exhilarating to see how his actions and morality compare to the “bad” (Lee Van Cleef) and “ugly” (Eli Wallach) characters in the story.

A stylistic breakthrough thanks to Leone’s rapid fire editing and the excellent score by Ennio Morricone, The Good, The Bad, and the Ugly is best known for its climactic final gunfight. It’s a moment that has inspired countless imitators, ripoffs, and parodies over the years, but no actor has managed to be as effortlessly cool as Eastwood. The Good, The Bad, and the Ugly is the perfect getaway film to get non-western fans interested in the genre.

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1 ‘Unforgiven’ (1992)

Directed by Clint Eastwood

A dark and deeply disturbing revisionist western, Unforgivenearned Eastwood the Academy Awards for Best Picture and Best Director that he had long since deserved. Despite a history of playing reluctant heroes, Eastwood cast himself against type by playing the ruthless former gunslinger Will Munny. The film chronicles Munny’s return to the world of violence when he is hired to bring the ruthless sheriff Little Bill (Gene Hackman) to justice.

Unforgiven served as a commentary on the western genre itself, and explored how cruel men have become mythologized as a result of the inherent violence within the American frontier. It’s a disturbing and often shocking film that shows Eastwood’s maturation as a filmmaker, and features one of his stronger acting performances as well. It’s hard not to compare every subsequent western film to Unforgiven, as the industry is still in awe of Eastwood’s climactic masterpiece.

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KEEP READING: The 10 Most Rewatchable Westerns, Ranked