Legendary Hollywood actor Clint Eastwood has directed many classic movies — and continues to do so in his 90s — but how do they all rank from worst to best? Best known for his iconic Western roles, Eastwood got his start as a supporting actor in the ’50s, made a name for himself in the ’60s as the leading Man With No Name in Serge Leone’s Spaghetti Western Dollars Trilogy, and began his directing career in 1971 with the sultry psychological thriller Play Misty For Me. Astoundingly, already roughly 20 years into his acting career, 1971 marked only the beginning of Eastwood’s 50+ years as a film director.
While his filmmaking legacy is mostly associated with Western films, Eastwood has taken on a variety of roles and movie genres as an actor-director. Even so, it’s fitting that Eastwood’s first Academy Award was for what was tentatively his last Western — at least until 2021’s Cry Macho — which Eastwood dedicated at the time to his former Western partner-in-crime Serge Leone. Since then, Eastwood’s name has been virtually synonymous with the Western genre, though his filmmaking career in the 21st century has covered everything from urban murder mysteries to sports dramas to a Japanese war film.
Ranked: Every Clint Eastwood Western, Ranked Worst To Best
No doubt, many of Eastwood’s most iconic roles — The Man With No Name, Dirty Harry, etc. — originate from movies he didn’t direct. However, the movies he did direct, many of which he also starred in, draw special fascination for movie lovers, as they each offer a glimpse into the workings of the man’s mind. On that note, here is every movie Clint Eastwood has directed, ranked from worst to best:
39. Firefox (1982)
A techno-thriller action film based on Craig Thomas’ 1977 novel of the same name, Firefox was shot on a $21 million budget, of which $20 million went to the special effects. With an anomalous rave review from Roger Ebert, who gave Firefox three-and-a-half stars out of four, Firefox largely pandered to the anti-KGB sentiments of Cold War-era Americans to predominantly negative critical reception. While nowhere near the impressive spectacle of its special effects-heavy contemporaries — Stars Wars, Blade Runner, etc. — Firefox does stand out as one of Eastwood’s more aesthetically “out there” films.
38. The Eiger Sanction (1975)
Closely competing with Firefox for Eastwood’s worst directed movie, The Eiger Sanction is largely viewed as a misstep in Eastwood’s career, not least of all because of the multiple injuries sustained during production, including the death of 26-year-old British climber David Knowles. With the actors — including Eastwood himself — performing many of the mountain-climbing stunts themselves in this action thriller, The Eiger Sanction took many dangerous risks that, despite provoking mixed reviews, earned the film praise for its climbing footage and tense action sequences.
37. The Rookie (1990)
Co-starring Eastwood with Charlie Sheen, while also featuring a Lara Flynn Boyle hot off the success of David Lynch’s Twin Peaks, The Rookie is a buddy-cop action film that follows the Eastwood-and-Sheen detective duo on their journey to take down a German crime lord in Los Angeles. With strange casting decisions (Puerto Rican Raul Julia and Brazilian Sônia Braga play Germans) and a tired, formulaic plot, The Rookie fared poorly with critics, despite a decent return in the box office.
Related: Every Which Way But Loose Is Clint Eastwood’s Most Successful Movie
36. Blood Work (2002)
Based on the Michael Connelly novel of the same name, Blood Work is a 2002 mystery thriller co-starring Eastwood with Jeff Daniels, Wanda De Jesús, and Anjelica Huston. The story follows an FBI agent who, after a heart transplant, investigates a serial killer. Noted for its “lethargic pacing,” Blood Work seemed at the time to represent a late-career tiredness in Eastwood’s filmmaking stamina — though, thankfully, this prognosis was wrong, as proven by the massive career-defining hits he’d go on to direct following this film.
35. Jersey Boys (2014)
Based on the 2005 Tony Award-winning jukebox musical, Jersey Boys follows the real-life musical group The Four Seasons, a four-man band comprised of Frankie Valli, Bob Gaudio, Nick Massi, and Tommy DeVito. Of the original members, both Valli and Gaudio joined Eastwood as executive producers on the project while also composing the film’s music.
34. Hereafter (2010)
A fantasy disaster drama film co-starring Matt Damon and Cécile de France, Hereafter tells three parallel stories about three people affected by death: George (Damon) is a factory worker who can communicate with the dead, Marie (de France) is a French journalist who survives a near-death experience, and Marcus (played by Frankie and George McLaren) is a British schoolboy who loses someone close to him. While praised for its ambitious, thought-provoking plot, Hereafter received overall mixed reviews.
33. Breezy (1973)
The third movie directed by Eastwood, Breezy is a romantic drama involving a teen hippie named Edith Alice “Breezy” Breezerman (Kay Lenz) and the divorced, middle-aged Frank Harmon (William Holden) who engage in an unconventional relationship that draws the ire of Harmon’s peers. While Breezy may feel very outdated to modern audiences, the movie is undoubtedly charming in a way that’s at once timeless while also serving as a distinct time capsule of the early-to-mid-70s — an era Eastwood has represented well in other timeless classics, such as Dirty Harry and Play Misty For Me.
Related: Why Clint Eastwood Turned Down Playing Superman
32. Midnight in the Garden of Good and Evil (1997)
The film adaptation of John Berendt’s book, Midnight in the Garden of Good and Evil follows the young journalist John Kelso (John Cusack) as he travels to Savannah, GA to ostensibly cover the city’s Christmas celebrations before becoming involved in a murder trial. A box office failure, the film’s quirky Southern subject matter mismatched with Eastwood’s spare directorial style, resulting in an odd tone that audiences found either unintentionally enjoyable or obnoxiously stilted.
31. Absolute Power (1997)
Playing a jewel thief who witnesses Secret Service agents murdering a woman, Eastwood both directs and stars in the political crime thriller Absolute Power, a movie adaptation of David Baldacci’s 1996 novel of the same name. When Eastwood learned the book was being adapted into film by screenwriter William Goldman (The Princess Bride), he expressed interest in making the movie with one caveat: that all the interesting, likeable characters killed off in the book survive in the film.
30. True Crime (1999)
Not to be mistaken with the critically panned Alicia Silverstone True Crime from 1995, Eastwood’s True Crime released during a major year in film history — which also saw the releases of The Matrix, Fight Club, Magnolia, and much more — though it was largely a box office bomb, grossing only $16 million against a $55 million production budget. While Eastwood’s failures typically come with praise for his acting, most critics agreed that Eastwood was miscast in this otherwise decent mystery thriller.
29. The 15:17 to Paris (2018)
On August 15, 2015, three young Americans travelling through Europe prevented a would-be terrorist attack on a train bound for Paris, saving upwards of 500 onboard passengers. Based on the autobiography The 15:17 to Paris: The True Story of a Terrorist, a Train, and Three American Heroes, Eastwood’s The 15:17 to Paris stars Spencer Stone, Anthony Sadler, and Alek Skarlatos as themselves — the three Americans centrally involved in the true story — who make the most of an otherwise clunky screenplay.
Related: Dirty Harry True Story: Was John Wayne Almost Cast Over Clint Eastwood?
28. J. Edgar (2011)
A polarizing biographical drama focusing on J. Edgar Hoover, the head of the FBI for nearly 50 years, J. Edgar boasts a major star-powered cast — Leonardo DiCaprio, Armie Hammer, Naomi Watts, Josh Lucas, Judi Dench, and Adam Driver (in his debut film role) — that earned the film praise for its powerhouse performances while drawing criticism for its confusing narrative and weak storytelling. Despite the film’s mixed reviews, J. Edgar marks another impressively ambitious title in Eastwood’s eclectic filmography.
27. The Gauntlet (1977)
Starring alongside Sandra Locke of The Heart Is A Lonely Hunter fame, Eastwood plays the gruff cop Ben Shockley who must escort the prostitute Augustina “Gus” Malley (Locke), a witness in a mob trial, from Las Vegas to Phoenix in this “Classic Clint” action-thriller movie. Praised as an endearingly “stupid movie” that focuses more on fun, high-stakes action than intellectual depth, The Gauntlet was a hit with the public, whereas critics were generally mixed.
26. Sudden Impact (1983)
The only Eastwood-directed film of the five Dirty Harry movies, Sudden Impact is the series’ penultimate film and one of the darkest of the saga, with “Dirty” Harry Callahan (Eastwood) investigating the murders of men who previously gang-raped a woman named Jennifer Spencer (played by Sondra Locke again). When Callahan gets himself romantically involved with Spencer, who’s revealed as the killer, Callahan finds his personal sense of justice at odds with his professional obligations as a police officer.
25. Heartbreak Ridge (1986)
Directed and produced by Eastwood, Heartbreak Ridge is an Eastwood affair through-and-through, with the war film even co-starring Eastwood as Marine Sgt. Thomas Highway alongside Marsha Mason, Everett McGill, and Mario Van Peebles. Centering on the story of Sgt. Highway as he prepares a platoon of undisciplined Marines for the American invasion of Grenada in 1983, Heartbreak Ridge opened to generally positive critical and audience reception, with special praise going towards the energetic, yet tender masculinity of Eastwood’s performance.
Related: How Cry Macho Is Different From Clint Eastwood’s Iconic Westerns
24. Space Cowboys (2000)
Featuring a star-studded cast, Space Cowboys follows the story of a group of Air Force pilots played by Eastwood, Tommy Lee Jones, Donald Sutherland, and James Garner who dream of serving their country as the first Americans to launch into outer space. Despite being pushed aside for a chimpanzee, the team stays true to their dream when, years later, they’re granted the assignment to launch into space to stop an orbiting Soviet satellite from crashing to earth.
23. White Hunter Black Heart (1990)
An adventure drama adapted from the 1953 book by Peter Viertel, White Hunter Black Heart is a semi-biographical account of Viertel’s experiences while filming 1951’s The African Queen, a classic movie that was shot on-location in Africa during a time when location shoots outside of the United States were rare. Based on the real-life director John Huston, Eastwood plays the gruff director John Wilson who becomes controversially more interested in shooting an elephant than shooting a film.
22. Invictus (2009)
A biographical sports drama based on the 2008 book Playing the Enemy: Nelson Mandela and the Game That Made a Nation by John Carlin, Invictus follows the events in South Africa surrounding the 1995 Rugby World Cup, namely as they pertain to the Springboks team who were predicted to play poorly after having only recently entered international competition following the dismantling of South Africa’s apartheid.
21. Bronco Billy (1980)
A Western comedy directed by and starring Eastwood, Bronco Billy follows Bronco Billy (Eastwood), the leader of a failing Wild West show, as struggles to stay afloat amid declining public interest. After encountering Antoinette Lily (Sondra Locke), a hoity-toity heiress, and hiring her as his new assistant, Billy finds new success after she agrees to performing in one of his shows. A modest commercial success, Bronco Billy’s self-referential quality in relation to Eastwood’s career has qualified it as a special benchmark title in his filmography.
Related: Cry Macho Is Much Better Because It Took Clint Eastwood So Long To Make
20. Honkytonk Man (1982)
Set during the Great Depression, Honkytonk Man sees Eastwood endearingly costarring with his son Kyle Eastwood. A Western singer dying from tuberculosis, Red Stovall (Clint Eastwood) goes on one last road trip with his nephew Whit (Kyle Eastwood) on a journey to the Grand Ole Opry in Tennessee, where Red hopes to finally achieve fame as a musician.
19. Flags of Our Fathers (2006)
Directed, produced, and scored by Eastwood, Flags of Our Fathers is an American war film about the 1945 Battle of Iwo Jima, namely the five Marines and one Navy corpsman responsible for triumphantly raising the flag on Iwo Jima. A companion film to Eastwood’s later movie Letters from Iwo Jima, Flags of Our Fathers takes the American viewpoint on the Battle of Iwo Jima for what would become a box office failure, despite positive reviews from the critics.
18. Pale Rider (1985)
An ethereal American Western fantasy, Pale Rider draws its title from the Book of Revelation, chapter 6, verse 8: “And I looked, and behold a pale horse: and his name that sat on him was Death, and Hell followed with Him.” As the proverbial pale rider of death, one of the Four Horsemen of the Apocalypse, Eastwood’s character Preacher is one of his more ghostly renditions of the cinematic cowboy. Released in 1985, Pale Rider become one of the highest-grossing Westerns of the ’80s.
17. The Mule (2018)
Nearing the ripe age of 90, Eastwood directed and produced 2018’s The Mule, which he also starred in as the 90-year-old horticulturist Earl Stone, a broke and lonely old man who accepts a job as a drug courier for a Mexican cartel. Taking on larger shipments following the success of his first courier job, Stone finds himself garnering the attention of the DEA. The movie is based on the true story of Leo Sharp, a World War II veteran who became a drug courier for the Sinaloa Cartel.
Related: Bruce Lee’s One Western Role Explained (& How It Was Different)
16. Sully (2016)
A biographical drama based on the 2009 autobiography Highest Duty by Chesley “Sully” Sullenberger and Jeffrey Zaslow, Sully stars Tom Hanks as Sullenberger, the pilot responsible for the 2009 emergency landing of US Airway Flight 1549 on the Hudson River, a heroic feat that, while earning him praise as a real-life hero, subjected him to an intense investigation calling into question his emergency-landing decision.
15. Changeling (2008)
Another Eastwood-directed movie based on a true story, Changeling follows the story of Christine Collins (Angelina Jolie), a single mother in 1928 Los Angeles who returns home one day to find her son, Walter, missing. When her “son” is found five months later in Illinois, Christine is horrified to realize that the boy isn’t her actual son, despite the aggressive insistence of the authorities who claimed to “find” him.
14. Bird (1988)
Revealing Eastwood’s penchant for jazz, Bird is a biographical film about the notorious bebop master saxophonist Charlie “Bird” Parker, a genius artist who truly loved only two things in his life: jazz and heroin. Tragically dying of a heroin overdose at the age of 34, Parker tested the patience of his wife, as brilliantly portrayed in this Eastwood-directed biopic.
13. American Sniper (2014)
The controversial biographical war drama centered on Navy SEAL sniper Chris Kyle (Bradley Cooper), a sniper credited with at least 160 confirmed kills, American Sniper instigated a minor culture war with its release in 2014, with both its supporters and detractors making it a phenomenal box office success as the highest-grossing war film of all time — as well as Eastwood’s highest-grossing film to date.
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12. Cry Macho (2021)
Released to both theaters and HBO Max, Cry Macho stars a 91-year-old Eastwood as a washed-up horse breeder who gets involved in his ex-boss’ custody battle, of a sort, over his young son, who’s being held captive by his alcoholic mother in Mexico. A coming-of-age road trip movie, Cry Macho sees Eastwood lecturing the boy on what it means to be “macho” with an authority that perhaps only Eastwood has, considering his intensely macho filmmaking career.
11. Richard Jewell (2019)
Another controversial Eastwood-directed film, though not as controversial as American Sniper, Richard Jewell tells the somewhat contemporary true story of Richard Jewell, the security guard who alerted police of the Centennial Olympic Park bombing at the 1996 Summer Olympics. Because no good deed goes unpunished, Jewell was subsequently harassed by the FBI and the media, both of whom wrongfully profiled Jewell as the bombing’s leading suspect.
10. A Perfect World (1993)
Starring Kevin Costner as Butch, an escaped state prisoner from Texas who kidnaps a young boy (T.J. Lowther), A Perfect World sees this unlikely duo develop a surprising bond with law enforcement hot on their trail. As a compassionate Texas Ranger, Red Garnett (Eastwood) understands Butch’s emotional dilemma, yet he continues pursuit after him in the name of the law and of the boy’s safety.
9. High Plains Drifter (1973)
Similar to his iconic role as the Man With No Name is Leone’s Dollars Trilogy, Eastwood plays a drifter with no name in the Western High Plains Drifter. Casually “drifting” into a small town where he earns his keep with his gun-slinging abilities, Eastwood’s drifter helps protect the town against bandits, while harboring a secret past connection to the town — unbeknownst to the town’s citizens.
Related: Clint Eastwood’s New Movie Confirms The Secret Truth Of His Entire Career
8. Mystic River (2003)
Adapted from Dennis Lehane’s 2001 novel of the same name, Mystic River is a neo-noir mystery crime drama starring Sean Penn, Tim Robbins, and Kevin Bacon as three childhood friends who grow up to find themselves involved in a murder — with one being the victim’s father, the other the murder’s official investigator, and the third the leading suspect. Surprisingly moving with expertly crafted, hypnotic pacing, Mystic River set an early tone for Eastwood’s impressive abilities as a director in the 21st century.
7. The Bridges of Madison County (1995)
A standout performance and directing effort from Eastwood, The Bridges of Madison County is a love story about a photographer who finds himself in a somewhat innocent, brief love affair with a married woman while on an assignment to take pictures of the historic bridges of Madison County. Though Eastwood’s sweet side wasn’t in question by this point in his otherwise action-packed filmography, The Bridges of Madison County revealed the actor’s deeply romantic depths.
6. Letters From Iwo Jima (2006)
The companion film to Flags of Our Fathers, Eastwood’s Letters from Iwo Jima takes the Japanese viewpoint on the Battle of Iwo Jima, told through the long-buried missives of the Japanese troops who fought and died at Iwo Jima. For a story commonly told as a patriotic example of the United States military prowess, Letters from Iwo Jima proved Eastwood capable of honestly and empathetically depicting two sides of a battle with one of the decade’s most moving war stories.
5. Gran Torino (2008)
Another massively successful hit by Eastwood, Gran Torino tells the story of the retired auto worker and Korean War vet, Walt Kowalski (Eastwood), who begrudgingly befriends an Asian teen who was peer pressured into attempting to steal Walt’s car. Through his consequent friendship (and unlikely mentorship) with the teen, Walt overcomes his deep racism to help the young man and eventually makes a major sacrifice to save him from his violent, gangbanging peers.
Related: Bruce Lee Used Clint Eastwood As A Model For His Hollywood Plan
4. Play Misty for Me (1971)
Eastwood’s first film as director, Play Misty For Me stars Eastwood as Dave Garver, a popular radio show host and all-around lady-killer whose inherent hunky charms attract the interest of an emotionally unhinged frequent caller (Jessica Walter). After straying from his girlfriend (Donna Mills) to hook up with the caller, Garver finds himself in over his head when she begins to stalk him and his girlfriend with increasingly violent intent. Thanks to both Eastwood’s and Walter’s respective legacies following the film’s release, Play Misty For Me has since become a beloved cult classic and, like 1973’s Breezy, a time capsule of the early ’70s.
3. The Outlaw Josey Wales (1976)
Beyond his roles in A Fistful of Dollars, For a Few Dollars More, and The Good, The Bad, and The Ugly, perhaps his most iconic Western role is from The Outlaw Josey Wales as the eponymous Josey Wales, a Missouri farmer whose family is murdered during the American Civil War by Union militia. Seeking revenge, Wales finds refuge among the Confederates, all of whom are eventually either killed by or surrender to the Union — with exception to Wales, who tries to make a new life for himself as an outlaw. In 1996, The Outlaw Josey Wales was deemed “culturally, historically, or aesthetically significant” by the United States Library of Congress.
2. Million Dollar Baby (2004)
A high point of Eastwood’s career and one of the best films of the aughts, Million Dollar Baby is a moving sports drama that follows the story of Frankie Dunn (Eastwood), a veteran boxing trainer in Los Angeles who, despite his antisocial reclusiveness, reluctantly agrees to train Maggie Fitzgerald (Hillary Swank), with whom he quickly forms a close bond. Garnering seven Academy Award nominations and winning four, Million Dollar Baby earned Eastwood his second Best Picture Oscar.
1. Unforgiven (1992)
Eastwood’s first Best Director Oscar win, however, was earned in 1992 with his seminal Western Unforgiven, a story about two groups of gunfighters warring with each other and a sheriff who’s supremely intolerant of vigilantism after a begrudged prostitute posts a bounty for the murder of the cowboys who abused and disfigured her. With this ostensibly serving as the highpoint of Eastwood’s Western film career, the actor-director officially declared his retirement from the Western genre, as he felt he’d only be retreading the same ground over and over following this Best Picture-winning effort. Of course, Clint Eastwood went back on this promise nearly 30 years later with his lead role in Cry Macho.
Next: Clint Eastwood’s Dirty Harry Franchise, Ranked
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About The Author
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Ryan Simón is a Feature Editor for Screen Rant, a writer and avid reader, and the founding editor of an art/culture magazine based in Montana.
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