The Best Clint Eastwood Movies of All Time, Ranked

It almost goes without saying that Clint Eastwood is one of the most iconic American actors of all time. That’s ironic, considering the fact that Eastwood ended up in Italy after failing to make it big in Hollywood. But after the legendary Dollars Trilogy, which featured him as ‘The Man with No Name,’ gained international acclaim, Eastwood became a hot commodity. It wasn’t long until he was directing and producing his own films, which allowed him to star in roles of his choice. Out of any actor-turned-director, Eastwood is undeniably one of the most successful, with seven decades of film experience.

Now in his 90s, it is said that Eastwood will retire with the film Juror No. 2, an all-star legal thriller. If that’s true, then Eastwood has already finished acting, and leaves behind an epic career that frequently reflects the sociopolitical evolution of America since the 1960s. While Eastwood’s personal politics often drew criticism from the more politically liberal Hollywood filmmakers, Roger Ebert defended his work by saying, “Clint Eastwood is one of the most admirable men in the history of motion pictures, and one of the few who has continued to grow in his art with every passing year.”

There are a lot of very good Clint Eastwood movies that could be here for whatever reason — The Bridges of Madison County and Magnum Force couldn’t be any more different from each other, but they both could be placed here, as could Two Mules for Sister Sarah or For a Few Dollars More. Hell, even a pretty lame movie like Paint Your Wagon is worth seeing, just to check out a vulnerable Clint Eastwood doing his best at a musical. But we have to restrict ourselves to the best of them all, and so here are Eastwood’s best movies as an actor, ranked.

Thunderbolt and Lightfoot

4/5

A car thief prevents the assassination of a bank robber who is hunted by his former gang. The robber convinces both his new and his former partners to work with him on a new heist.

Release Date: May 22, 1974
Director: Michael Cimino
Runtime: 1h 55m
Writers: Michael Cimino

The great but often misunderstood Michael Cimino (The Deer Hunter, Heaven’s Gate) began his directorial career with Thunderbolt and Lightfoot, after co-writing Clint Eastwood’s second Dirty Harry film, Magnum Force. He wrote this film himself, and it’s representative of his oddly loose and rambling style, which is perfect here thanks to the wonderful pairing of Clint Eastwood and Jeff Bridges, who both star as the titular thieves.

The Very Entertaining Beginning of Michael Cimino’s Directorial Career

Thunderbolt and Lightfoot is a fun thriller that nonetheless shakes with surprising bursts of violence, and the film isn’t afraid to dive deep into increasingly dark moments as it progresses. Clint Eastwood was arguably a big help in the final project, aside from his memorable performance as a betrayed master thief. He supposedly refused to do more than three takes, forcing the perfectionist Cimino to progress much quicker than he would’ve. The result is a swift and well-paced rollercoaster of emotions.

14 Hang ‘Em High

Hang ‘Em High (1968)

Hang ‘Em High is a Western film directed by Ted Post and stars Clint Eastwood as Jed Cooper, a man who seeks justice after surviving a lynching. The narrative explores themes of vengeance and morality as Cooper, appointed as a lawman, navigates his quest for retribution in the face of frontier justice. The film also features notable performances by Inger Stevens and Pat Hingle.

Release Date: April 12, 1968
Director: Ted Post
Cast: Clint Eastwood , Inger Stevens , Ed Begley , Pat Hingle , Ben Johnson
Runtime: 1h 54m
Writers: Mel Goldberg , Leonard Freeman

Hang ‘Em High is an interesting revenge film, a Western that meditates on justice versus vigilantism, and law versus emotion. It marked the return of Clint Eastwood to Hollywood after his time in Italy, and the film certainly feels like an Americanized Spaghetti Western (an “apple pie Western,” as one critic put it). The film follows the slow justice of an innocent man who is wrongly hanged and left for dead after purchasing stolen cattle. The man is rescued by a Marshal and offered to take on the job of Marshal himself.

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The emotional balance thus has Eastwood’s character hunting down the men who hung him but trying to restrain himself from simply killing them, and instead bringing them in for justice. It’s almost a precursor to Dirty Harry in that sense, what with its praise of policing and its view of civilization as violence moderated by authority. It makes sense then that Ted Post would go on to direct a Harry film with Eastwood, Magnum Force.

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13 Kelly’s Heroes

Kelly’s Heroes (1970)

4/5

Kelly’s Heroes is a war comedy film set during World War II, directed by Brian G. Hutton. Starring Clint Eastwood, Telly Savalas, and Donald Sutherland, the film follows a group of American soldiers who, upon discovering information about a hidden cache of Nazi gold, embark on a rogue mission to retrieve it. Balancing humor with action, Kelly’s Heroes offers a unique take on the war genre.

Release Date: June 22, 1970
Director: Brian G. Hutton
Runtime: 144 Minutes
Writers: Troy Kennedy Martin

Kelly’s Heroes is a very fun mash-up of World War II adventure movies and action heists. Director Brian G. Hutton only made two war films, this and Where Eagles Dare; they both have Clint Eastwood, and they’re both a blast. Kelly’s Heroes follows a group of American soldiers in 1944 France who plot to steal millions of dollars in gold bars that the Nazis have stashed behind German lines.

A Great Ensemble Cast

Eastwood hated the title of Kelly’s Heroes, rightfully thinking it sounded too much like the TV show Hogan’s Heroes, and disliked what MGM cut from the film, but it’s still a delightful ensemble film with great turns from Eastwood, Donald Sutherland, Telly Savalas, Don Rickles, Carroll O’Connor, Harry Dean Stanton, and more. There’s a ton of character-based humor in the movie, and some classic lines of dialogue, with Eastwood balancing out the wackiness.

12 Play Misty for Me (1971)

Play Misty for Me

4/5

Popular radio show host Dave Garver (Clint Eastwood) becomes restless in his relationship with his girlfriend (Donna Mills). Impulsively, he goes out and sleeps with a woman (Jessica Walter) he meets at a nightclub. After the fact, he finds out she was not an anonymous hookup, but an obsessive fan who has called in repeatedly to request he play the song “Misty.” Garver soon discovers extricating himself from the woman will be no easy feat as she becomes increasingly psychotic.

Release Date: October 20, 1971
Runtime: 1h 42m

1971 was a major year for Clint Eastwood; it was the year of Dirty Harry and the year of his directorial debut. Play Misty for Me may seem very different from his other films (it’s an erotic thriller where he plays a poetic radio DJ), but its theme is subliminally pertinent across many Eastwood films — the masculine fear of losing control and power to women, or the Freudian fear of castration. Play Misty for Me follows a radio disc jockey who begins an intense relationship with a frequent caller into his show.

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Eastwood’s direction is lurid, and he’s wise to lean on the great cinematographer Bruce Surtees, who he knew from Don Siegel’s films and would go on to work with him on eight more films. They create a paranoid, shadowy thriller, made so much more effective by Jessica Walter, who is phenomenal as the unhinged obsessive, Evelyn. Arrested Development fans would do themselves a favor to look back on her fantastic work here.

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11 The Beguiled (1971)

The Beguiled (1971)

4.5/5

While recuperating in a Confederate girls’ boarding school, a Union soldier cons his way into each of the lonely women’s hearts, causing them to turn on each other, and eventually, on him.

Release Date: March 31, 1971
Director: Don Siegel
Cast: Clint Eastwood , Geraldine Page , Elizabeth Hartman , Jo Ann Harris , Darleen Carr , Mae Mercer , Pamelyn Ferdin , Melody Thomas
Runtime: 1h 45m
Writers: Albert Maltz , Claude Traverse (uncredited)

Clint Eastwood and Don Siegel were one of the best actor-director pairs in film history, and you’ll see many of their movies in this list. Eastwood would go on to emulate Siegel’s style more than anyone else’s in his own work as a director. The Beguiled is arguably their strangest film together, and the fact that it came out the same year as Dirty Harry is a testament to their range. The film explores the psychosexual angst that ensues at a Mississippi girls’ school during the Civil War after one student discovers a wounded Union soldier.

A Dreamy Feminine Anomaly in Eastwood’s Career

The Beguiled is a very dreamy movie and a surprisingly radical one. It’s genuinely striking to see one of the mascots of masculinity, the squinting, gunslinging Eastwood, helpless at the hands of young girls and their desires, trying to survive and hide from the Confederacy. It flips the script on the normal male gaze, presents an anti-Vietnam message, and brilliantly uses the Civil War as an allegory — men and women may be different, but they’re both capable of evil, violence, and selfishness. Sofia Coppola’s remake with Colin Farrell was surprisingly tamer and less bizarre, but still good.

10 Where Eagles Dare

Where Eagles Dare

4/5

Where Eagles Dare follows a Special Operations Executive team of men attempting to save a captured American General from the fictional Schloß Adler fortress, except the mission turns out not to be as it seems.

Release Date: December 4, 1968
Runtime: 2h 35m
Writers: Alistair MacLean

Another rousing World War II adventure film from Brian G. Hutton and Clint Eastwood, Where Eagles Dare is a vibrant and cool ensemble actioner. Richard Burton leads the film as the head of a team of British commandos who are tasked to work with an American Army Ranger (Eastwood) to rescue an important Brigadier General who’s being held in a mountaintop fortress.

A Perfect Setting and Great Cast

The alpine village that the team must infiltrate makes for an extremely cool, James Bond-type setting for this WWII spy thriller. The movie takes its time, letting the great relationship between the very different Eastwood, Burton, and Mary Ure develop. The epic escape has been emulated many times in the past 55 years, and for good reason.

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9 Dirty Harry

Dirty Harry

Release Date: July 14, 1971
Director: Don Siegel
Cast: Clint Eastwood , Harry Guardino , Reni Santoni , John Vernon , Andrew Robinson , John Larch
Runtime: 102
Writers: Harry Julian Fink , Rita M. Fink , Dean Riesner , John Milius , Jo Heims

Don Siegel’s classic crime thriller, Dirty Harry, launched a new era for Clint Eastwood and a new franchise. Instead of ‘The Man with No Name’ of his ’60s movies with Sergio Leone, he was now ‘Dirty’ Harry Callahan, a tougher, angrier man with less humor and more authority. An inspector for the San Francisco Police Department, Harry is the perfection of a prototype which began with Eastwood and Siegel’s first film, Coogan’s Bluff — a ‘maverick’ cop is always in trouble with his superiors in the department, but dammit, he gets the job done.

An Action-Packed Right-Wing Fantasy

Critics like Pauline Kael and Roger Ebert have called Dirty Harry a very entertaining piece of fascist propaganda, and they’re certainly right to some degree. As Kael wrote for The New Yorker, “Dirty Harry is not about the actual San Francisco police force; it’s about a right-wing fantasy of that police force as a group helplessly emasculated by unrealistic liberals.” However, Siegel is a great director (and was a liberal, just a pessimistic one), and he makes the film hip and thrilling in many ways, and purposefully ugly in others. It’s a classic in many respects, even if it’s a little uncomfortable.

8 High Plains Drifter (1973)

High Plains Drifter

4.5/5

A gunfighting stranger comes to the small settlement of Lago. After gunning down three gunmen who tried to kill him, the townsfolk decide to hire the Stranger to hold off three outlaws who are on their way.

Release Date: April 6, 1973
Runtime: 105 Minutes
Writers: Ernest Tidyman

High Plains Drifter is a quintessential Eastwood Western that shows he was much more than a one-trick Spaghetti Western pony, and it’s the first truly great film he directed. While Play Misty For Me showed that he could craft nail-biting thrillers set within the current day, High Plains Drifter proved that Eastwood had learned all the right lessons from his work with Leone, but added his own violent sensibilities. In fact, it’s the sheer darkness of High Plains Drifter that made it stand out.

A Nasty Cruel Clint Eastwood

Eastwood starred in the film as a remorseless, unnamed killer, and certainly pushed the film to the limits of its R-rating. He’s a seemingly supernatural stranger who arrives in a corrupt town and suddenly takes charge. The Stranger makes Dirty Harry Callahan look like Mr. Rogers; he’s a force of violence, and the film doesn’t hold back on his cruelty (dragging a woman by the hair, raping another, dislocating people from their homes, forcing everyone to work pointless jobs, shooting anyone who interferes). When he paints the word “Hell” over the town sign, it makes sense. It’s a disturbing meditation on violence and karma, something that Eastwood would somewhat remake with the less nihilistic and superior Pale Rider.

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7 In the Line of Fire (1993)

The 1990s saw an increased fascination with conspiracy theories and mistrust of the government, leading to some great political thrillers (JFK, Shadow Conspiracy, Patriot Games, The General’s Daughter, Enemy of the State, Mad City, and Clint Eastwood’s own Absolute Power). One of the best of the decade was In the Line of Fire, a taut and realistic cat and mouse thriller about a Secret Service agent named Frank and a mysterious murderer planning to assassinate the President of the United States.

A Tense Web of FBI and CIA Conspiracy

Jeff Maguire’s script is a deliciously tangled web of intrigue, with Eastwood’s aging Secret Service agent the only active agent who was around during the Kennedy assassination. The shadowy killer taunts him and develops a dark relationship with him as Frank gets pulled into the shadier aspects of the FBI and CIA. Director Wolfgang Petersen (Das Boot, Air Force One) is a master of building tension, and that’s on full display here.

6 Pale Rider (1985)

Pale Rider (1985)

5/5

This Western film revolves around a mysterious preacher who arrives in a struggling mining camp, where the residents are pitted against a greedy mining company encroaching on their land. With his enigmatic past and formidable skills, the preacher helps the miners defend their rights, invoking themes of redemption and conflict.

Release Date: June 28, 1985
Cast: Clint Eastwood , Michael Moriarty , Carrie Snodgress , Chris Penn , Sydney Penny , Richard Dysart , Richard Kiel , Doug McGrath , John Russell
Runtime: 1h 55m
Writers: Michael Butler , Dennis Shryack

The 1980s saw Eastwood exploring a few different genres; he finally got the chance to direct one of the entries in the Dirty Harry series with Sudden Impact, and showed his interest in telling stories about the American military in 1986’s Heartbreak Ridge. He even directed the biopic Bird about Charlie Parker, which made Forest Whitaker a star. However, that doesn’t mean that Eastwood had forgotten his roots; his 1985 film Pale Rider was actually the highest-grossing western of the 1980s.

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Pale Rider showed a maturation in Eastwood’s style, and in many ways is a remix of High Plains Drifter but with better direction and a sense of purpose. If that former film saw hellish vengeance play out against the inherent evil of humanity, Pale Rider finds genuine justice restored to a town, with a belief in decent humanity triumphing over evil. Eastwood plays a ghostly form of death that comes to defend the innocent civilians of a small town in California from a greedy group of oil prospectors. It’s the closest he’s ever come to directing a supernatural movie, and to veering away from conservatism into genuine anti-capitalism.

5 Escape from Alcatraz

Escape from Alcatraz

4.5/5

In early 1960 Frank Morris, a criminal who has absconded from other facilities, arrives at the maximum security prison on Alcatraz Island. Alcatraz is unique within the US prison system for its high level of security, and no inmate has ever escaped. Frank is determined to be the first.

Release Date: June 22, 1979
Director: Don Siegel
Runtime: 1h 52m
Writers: Richard Tuggle

Siegel and Eastwood strike gold again in the masterfully efficient, matter-of-fact prison escape film, Escape from Alcatraz, which ranks among the greatest of the genre. Their last film together, the 1979 picture is based on a true story and tells it with an almost documentary-like sense of purpose and accuracy. It’s a very libertarian film, which is a fitting middle ground for Siegel and Eastwood, and one of the most blatantly anti-authoritarian films of either men’s careers. A deep respect is created for Eastwood’s character, Frank Morris, and there’s a genuine emotional resonance to his relationships and actions in the prison as he plots his escape.

A Perfect End to Eastwood and Siegel’s Collaboration

Escape from Alcatraz is much less action-based than other Siegel and Eastwood films, taking its confines seriously and building slow tension as Frank and three other men develop a plan to escape. Meanwhile, they have to survive criminal psychopaths and a sadistic Warden. It’s naturalistic but also gradually exhilarating, building to one of the greatest endings in film history.

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4 A Fistful of Dollars

A Fistful of Dollars

5/5

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.

Release Date: January 18, 1964
Director: Sergio Leone , Monte Hellman
Cast: Clint Eastwood , Marianne Koch , Gian Maria Volonte , Wolfgang Lukschy , Sieghardt Rupp , Joseph Egger
Runtime: 1h 39m
Writers: Ryûzô Kikushima , Akira Kurosawa , A. Bonzzoni , Víctor Andrés Catena , Sergio Leone , Jaime Comas Gil

A Fistful of Dollars is really where it all started — Clint Eastwood’s recognition as an actor, the birth of Spaghetti Westerns, and a change in the mainstream Western protagonist. The beginning of Sergio Leone’s brilliant Dollars Trilogy with Eastwood, the funny Western is one of many remakes of Akira Kurosawa’s classic film, Yojimbo, which would inspire Eastwood’s own career as a director. He plays The Man with No Name for the first time here, as a stranger who saunters into a internally divided town on the U.S. border with Mexico. As in Yojimbo, he manages to play each warring side against each other.

Setting the Stage for a Trilogy and Clint Eastwood’s Career

Yojimbo and then A Fistful of Dollars set the blueprint for many subsequent Eastwood Westerns — an extremely skilled stranger rides into town, outwits all the evil townsfolk and helps the completely innocent, and rides out of town alone toward the horizon. It’s an ethically ambiguous, darkly funny, less emotional, and more stylized take on the classic Western paradigm we see in films like Shane. Even the very ending of A Fistful of Dollars has been replicated in multiple Eastwood films.

But A Fistful of Dollars does it with more panache and intelligence than almost any other, and became universally recognized for its oddly international twist on classic American symbols. Eastwood is just about as cool as he’s ever been, leading the film with smarts and swagger.

3 Million Dollar Baby

Million Dollar Baby is quite likely Clint Eastwood’s last great acting role, although his performance was one of the few Oscar nominations not to win at the 77th Academy Awards (where the film won Best Picture, Best Director, Best Actress, and Best Supporting Actor). The performance was so good that it essentially set the template for every other Eastwood performance from then on — a cantankerous man with genuine sins who also has a deep moral conviction lurking within him.

A Powerful and Emotional Tragedy

Million Dollar Baby remains one of the hardest films to rewatch; it’s a poignant and very painful tragedy about two lost souls who find each other, experience what they wanted out of life for one ephemeral moment, and then have to part ways in a terribly sad way. Eastwood plays the boxing trainer Frankie Dunn and an incredible Hilary Swank portrays his young protégé, Maggie Fitzgerald, an aspiring boxer who emerges from poverty in the Ozarks to eventually compete in a million-dollar Las Vegas game. The deeply emotional work Eastwood does in the film’s final 30 minutes is some of the best of his career.

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2 The Good, the Bad and the Ugly

The Good the Bad and the Ugly

5/5

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 23, 1966
Director: Sergio Leone
Runtime: 2h 57m
Writers: Luciano Vincenzoni , Sergio Leone , Agenore Incrocci , Furio Scarpelli

The Good, the Bad and the Ugly is rightfully considered one of, if not the greatest Western of all time. Sergio Leone and Clint Eastwood put everything they’d learned from the previous two films in the Dollars Trilogy into this epic masterwork of style and stares. While Eastwood himself is less of a main character than he was in the previous two films, he gives a fantastic performance with lots of range, showing deep anger, begrudging humanity, and utter desperation. He plays one of three men on the hunt for a stash of Confederate gold.

A Perfect Trilogy and Trio

Lee Van Cleef makes a phenomenal villain here as Angel Eyes, a disturbing mercenary who takes genuine pleasure in killing; the famous close-ups of his eyes are especially powerful. Eli Wallach is hilariously energetic as Tuco ‘The Rat,’ who finds himself in an odd and potentially deadly ‘frenemy’ relationship with Clint Eastwood’s ‘Blondie’ (or The Man with No Name). They both leave each other for dead, and they both save each other from death. It’s a fun and unpredictable relationship for the usually lonesome Man with No Name, and the film builds to an epic conclusion with imagery and sounds that have become eternally iconic in the cultural zeitgeist.

1 Unforgiven (1992)

Unforgiven (1992)

5/5

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.

Release Date: August 7, 1992
Runtime: 2hr 10min

The 1990s saw Eastwood turning his interests mostly towards crime thrillers with projects such as the electrifying thriller True Crime, the more comedic buddy comedy The Rookie, the political thriller Absolute Power, and the underrated crime drama A Perfect World, which bore a lot in common with his Western classics and featured one of Kevin Costner’s best performances. A Perfect World was perhaps the first film of Eastwood’s late period style, which has been marked by deep sentimentality, nostalgia, and a wariness toward violence. But before Eastwood could get to that point in his career, he had to exorcise all his demons with the Western masterpiece, Unforgiven.

Unforgiven Marked the End of a Western Era

Unforgiven isn’t only Eastwood’s best Western, but the film that finally won him an Oscar (for Best Picture and Best Director). Honestly, the fact that he lost the Best Actor Oscar to Al Pacino in Scent of a Woman remains a grave mistake to this day. Unforgiven marked the end of an era and felt like a “legacy sequel” to all the iconic Western anti-heroes that Eastwood had played in the past. Here, he portrays an old outlaw on hard times who needs to take on a bounty-hunting job to hunt down cowboys who disfigured a woman in a brothel. However, other bounty hunters and a sadistic sheriff are all ready to get involved.

Clint Eastwood put everything left he had to say about the American Western and its many themes and styles into Unforgiven. It’s a film that reckons with the violence of the genre and of the many murderous characters he played throughout his career. If anything, it’s a melancholic goodbye to the genre that made him famous, and Eastwood hasn’t made a Western since.