This Is the Worst Clint Eastwood Movie of All Time

A skip tracer (Eastwood) and his bounty (Peters) contend with various obstacles in this stale adventure comedy. Eastwood met future romantic partner actress Frances Fisher on the set and she would later give birth to their daughter Francesca.

This critically lambasted buddy-crime-comedy, which takes place in the 1930s, pairs a straitlaced police lieutenant (Eastwood) with an unpredictable private eye (Reynolds). Putting their differences aside, the begrudging partners take on the Kansas City mob. Both lead stars played heavily into their respective personas at the time.

One of Eastwood’s lesser directorial efforts finds him playing a veteran detective on the path for revenge. The only thing getting in his way is a young rookie partner (Sheen), who insists on playing by the rules. The film was quickly out-muscled in theaters by “Home Alone,” which was still reigning over the box office in its third week of release.

Former trucker turned bare-knuckle brawler Philo Beddoe (Eastwood) returns for this blockbuster sequel to 1978’s “Every Which Way But Loose.” With an orangutan for a sidekick, Beddoe is drawn back into the violent world he was trying to leave behind.

Based on a bestselling novel, this Cold War actioner follows a fearless pilot (Eastwood) behind Soviet lines on a top secret mission. Roger Ebert called it a “slick, muscular thriller that combines espionage with science fiction.” Most of Ebert’s fellow critics weren’t nearly as impressed.

A retired FBI profiler (Eastwood) tracks down a serial killer in this adaptation of a Michael Connelly novel. As the investigation proceeds, the profiler discovers that he and the killer may share a history. Eastwood’s then-wife Dina appears as a reporter.

This action comedy sends bare-knuckle fighter Philo Beddoe (Eastwood) and his pet orangutan Clyde on the search for a missing country singer. It defied plenty of negative reviews on its way to box office success, becoming the fourth highest-grossing film of 1978.

This poorly-aged Western musical chronicles the misadventures of two gold prospectors (Eastwood and Marvin) and their shared wife (Seberg). Its disastrous production and box office failure motivated Eastwood to assert more control and become a director.

The fifth and final Dirty Harry movie puts the famous detective on the trail of a devious killer, who’s compiled a list of celebrity victims. It was one of three Eastwood films directed by his stunt double Wayne “Buddy” Van Horn.

An aging journalist (Eastwood) has mere hours to clear an innocent Death Row inmate in this plodding thriller. Eastwood’s former wife Dina, daughter Francesca, and former partner Frances Fisher all appear in supporting roles.

The fourth installment of the Dirty Harry franchise is the only one to feature Eastwood as director. A vigilante rаpe victim is picking off her attackers one by one and only Callahan can stop her. This is the film that introduced the iconic phrase, “Go ahead, make my day.”

While robbing a billionaire’s mansion, an expert jewel thief (Eastwood) witnesses a heinous crime. So goes this political thriller from a screenplay by William Goldman. Writing for Chicago Reader, critic Jonathan Rosenbaum called it a “rather slack thriller that oddly recalls a couple of Hitchcock’s lesser movies.”

Eastwood was 90 years old when he directed and starred in this lackluster drama, which takes place in 1979. Tasked with returning a young boy to Mexico, a washed-up horse breeder (Eastwood) embarks on a dangerous and redemptive journey.

Modern cowboy Bronco Billy (Eastwood) tries to keep his Wild West show afloat in this comedy flop. According to legend, it’s one of Eastwood’s personal favorites among his own films. His children Alison and Kyle play a pair of orphans in uncredited roles.

An aging baseball scout (Eastwood) is reunited with his estranged daughter (Adam) in this 2012 sports drama. Critic Tom Charity called it “fundamentally sound and solid entertainment with a deep-rooted conviction that how we treat each other matters.” Other critics were more disparaging, pointing to the film’s rote execution and sappy melodrama.

A former government assassin (Eastwood) comes out of retirement for one last job in this dated spy thriller. It remains best known for a number of epic action sequences, many of which take place on a perilous mountain terrain.

Eastwood upends his Dirty Harry persona in this dramatic thriller, playing a flawed and vulnerable cop named Ben Shockley. While escorting a murder witness across state lines, Shockley must evade numerous attempts on his life.

The third installment of the Dirty Harry franchise follows the famous cop as he tries to take down a group of domestic terrorists. While too busy to handle directing duties, Eastwood still made a number of major creative decisions behind the scenes.

Eastwood and a fellow cast of Hollywood veterans head into space on an important mission in this adventure drama. It came out shortly after films such as “​​Armageddon” and “Deep Impact” and plays upon similar story tropes.

Eastwood returns yet again to the police thriller sub-genre in this noirish slasher flick, which takes place in New Orleans. As he searches for an elusive serial killer, Detective Wes Block (Eastwood) confronts the dark and dangerous side of his own identity.

Begrudgingly drawn out of retirement, a former bounty hunter (Eastwood) tracks down a Mexican revolutionary in this violent Western. Famous author Elmore Leonard – who began his career writing Western short stories and novels – penned the script.

This recent crime drama tells the reportedly true story of a 90-year-old war veteran (Eastwood) turned drug mule for the Mexican cartel. It’s the second of three collaborations between Eastwood and screenwriter Nick Schenk, who also wrote “Gran Torino” and “Cry Macho.”

This fish-out-of-water action comedy marked the first time that Eastwood teamed up with director and frequent future collaborator Don Siegel. It follows straightlaced Arizona Deputy Sheriff Walt Coogan (Eastwood) to Manhattan, where he clashes with the local personalities.

Eastwood plays an aging gunnery sergeant on the brink of retirement in this American war drama. While grappling with an alcohol problem, he trains a platoon of young marines before the 1983 invasion of Grenada.

A year before “Dirty Harry,” Eastwood and director Don Siegel churned out this romantic Western adventure. Sparks fly between a Civil War veteran (Eastwood) and a nun (MacLaine), who help Mexican revolutionaries capture a French fort.

Based on a 1953 novel by Peter Viertel, this adventure drama recounts the making of 1951’s “The African Queen” – for which Viertel was one of the screenwriters. Eastwood’s John Wilson is a thinly veiled portrait of director John Huston, whose obsessions with hunting threatened to derail the entire project. It opened to relatively positive reviews but floundered at the box office.

“Dirty” Harry Callahan is on the trail of vigilante cops in the franchise’s second installment. The premise was partially crafted as a response to the controversial first film, in which Callahan resorts to some vigilante tactics of his own.

An ailing country singer (Eastwood) heads to Nashville for one last shot at glory in this Depression-era dramedy. Along the way, he and his nephew engage in a series of misadventures. Playing the nephew is Eastwood’s son Kyle, a musician in real life.

The affair between a radio DJ (Eastwood) and a female fan turns dangerous in this psychological thriller. Eastwood’s directorial debut, it reportedly wrapped four days early and came in at $50,000 under budget. He would continue to take an economic and workmanlike approach to directing for the rest of his career.

From the director of “The Deer Hunter” comes this lively crime caper, in which a group of bank robbers enact a dangerous heist. “It’s Eastwood and Bridges’ film, and their ill-defined, tender friendship makes the movie,” wrote critic Keith Phipps for The Dissolve.

Eastwood followed the iconic “Dollars Trilogy” with this similarly gritty Western, the first feature produced by his own production house (now known as Malpaso Productions). He plays Deputy US Marshal Jed Cooper, who seeks brutal vengeance on his former attackers.

This feel-good documentary spans the legendary career of laughman Don Rickles, who appeared in a number of stand-up specials, talk shows, and films. One among a number of high-profile interviewees, Eastwood is joined by the likes of Robert De Niro, Billy Crystal, Whoopi Goldberg, and others.

Eastwood was staging a major career comeback and Costner was at the height of his fame when they collaborated on this successful crime drama. It centers on the unlikely friendship between an escaped convict (Costner) and his kidnap victim, with a Texas Ranger (Eastwood) hot on their trail.

Soldiers cross enemy lines to steal Nazi gold in this absurdist war comedy, partially inspired by true events. It sits alongside satires such as “M*A*S*H” and “Catch-22,” which likewise used historical wars as a subtext for Vietnam.

This political thriller depicts the deadly game of cat-and-mouse between a secret service agent (Eastwood) and brilliant assassin (Malkovich). A ticking clock looms over the action, with the President’s life in the balance. Expert pacing and top-notch performances keep viewers glued to their seats.

Eastwood returned to the genre that made him famous in this critical darling, which became the highest-grossing Western of the 1980s. A mysterious preacher (Eastwood) drifts into town and gets embroiled in a land dispute between local villagers and a greedy mining company. Rife with allegory, the film also draws upon themes and plot points from his previous output.

Scottish author Alistair MacLean wrote the screenplay (based on his novel) for this WWII adventure, in which Allied intelligence agents storm a Nazi castle. As the action unfolds, our supposed heroes discover a traitor in their midst. The title takes its name from Shakespeare’s “Richard III” and the following quote: “The world is grown so bad, that wrens make prey where eagles dare not perch.”

Based on a bestselling novel, this hit drama chronicles the four-day love affair between a lonely farm wife (Streep) and traveling photojournalist (Eastwood). It takes place in 1965 and reaps genuine emotion out of small, intimate moments. Streep earned an Oscar nomination for Best Actress.

This poignant mix of drama and thriller is the second-highest grossing film of Eastwood’s career. It centers on the contentious relationship between a surly veteran (Eastwood) and his Hmong American neighbors, which blossoms into a loyal friendship. When a local gang enters the picture, the story takes on a violent and ultimately redemptive dimension.

The first Western with Eastwood at the helm finds him playing into the mysterious persona he established in previous works. Known only as The Stranger, he’s tasked with protecting a small settlement from invading outlaws. Fellow genre legend John Wayne was reportedly not a fan.

The film that introduced “Dirty” Harry Callahan (Eastwood) remains controversial in its brutal disregard for standard law enforcement practices. Callahan would argue that he does whatever it takes to get his man, in this case the menacing Scorpio Killer. Multiple sequels would follow.

Eastwood and director Don Siegel collaborated for the last time on this prison-based thriller, about the most famous escape in modern history. Along with two fellow inmates, a bank robber (Eastwood) plans to break out from the country’s most secure penitentiary.

This revisionist Western takes place during and after the Civil War and stars Eastwood in the title role. In the wake of a violent massacre, Wales goes on the run from Union soldiers and bounty hunters. A commercial success, it earned $31.8 million at the domestic box office on a budget of $3.1 million.

This harrowing sports drama tells the story of an ambitious female fighter (Swank), who rises in the ranks with help from her aging trainer (Eastwood). It won four Academy Awards, including Best Picture and Best Director. Bring tissues.

The second installment of an iconic trilogy follows two bounty hunters (Eastwood and Van Cleef) as they track down a ruthless bandit. “Here is a gloriously greasy, sweaty, hairy, bloody and violent Western. It is delicious,” wrote Roger Ebert in his three-star review.

This groundbreaking spaghetti Western kicked off Leone’s “Dollars Trilogy” and established Eastwood as a budding film star. His character is occasionally referred to as Joe, but remains best known as the Man With No Name. Loosely inspired by Akira Kurosawa’s “Yojimbo,” the film’s gritty tone and radical style upended genre conventions.

Playing to all of Eastwood’s creative and performative strengths, this Western masterpiece offers an uncanny parallel to his legacy within the genre. He embodies the role of retired gunslinger William Munny, who hops back into the saddle for one final job. It won four Academy Awards, including Best Picture and Best Director.

Leone’s “Dollars Trilogy” concluded with this gritty Western, in which three bounty hunters (Eastwood, Wallach, Van Cleef) search for a fortune in buried treasure. Relentless violence, stylish camerawork, and Ennio Morricone’s timeless score propel the narrative toward its epic conclusion. Eastwood’s career was likewise propelled into Hollywood’s upper stratum.