Special Report
This Is the Worst Clint Eastwood Movie of All Time
Published:
Clint Eastwood has had a long and storied career, spanning almost 65 years. He has directed almost 40 films and had roles – from miniscule, uncredited ones to Oscar-nominated starring turns – in at least 60 of them. Many have been highly praised, but not all of them, and the worst Clint Eastwood movie of all time is 1989’s “Pink Cadillac.”
Eastwood is a unique figure in Hollywood. He started out as a TV star in a mediocre show, “Rawhide.” He made the jump to movies by becoming a star of several films that were not even made in America. Known as “Spaghetti Westerns”, these were made in Italy in the 1960s and included “A Fistful of Dollars” (1964), “For a Few Dollars More” (1965), and “The Good, the Bad and the Ugly” (1966).
From there he made the jump to becoming one of the most famous movie cops of all time in “Dirty Harry” (1971) and its sequels. Later, Eastwood, who is now 91, directed, produced, and starred in some of the most highly regarded movies ever. Of these, two – “Unforgiven” (1992) and “Million Dollar Baby” (2004) – won him Best Picture and Best Director Oscars. (See where Eastwood’s efforts rank among the best Western films of all time).
While he’s tackled just about every type of character or subject, Eastwood’s legacy remains closely tethered to the two sub-genres he helped reinvent: revisionist Westerns and police thrillers. His early collaborations with director Sergio Leone introduced a new kind of protagonist, whose rugged individualism provided a stark contrast to John Wayne’s patriotic nobility. Along similar lines, his “Dirty Harry” Callahan was a unique breed of law enforcer, the kind that doesn’t mind breaking a few rules – or a few thumbs – in his pursuit of justice.
To choose the worst movie in which Clint Eastwood starred – some of which he also directed – 24/7 Tempo developed an index with the 20,000+ movies in our database using average ratings on IMDb, an online movie database owned by Amazon, and a combination of audience scores and Tomatometer scores on Rotten Tomatoes, an online movie and TV review aggregator, as of January 2022. Only motion pictures in which Clint Eastwood received billing among the top four actors on IMDb or movies he directed were considered.
Click here to see Clint Eastwood movies ranked worst to best
48. Pink Cadillac (1989)
> Combined score: 0.96 — #19,300 highest out of 22,286 movies
> Director: Buddy Van Horn
> Also starring: Bernadette Peters, Timothy Carhart, Tiffany Gail Robinson
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.
[in-text-ad]
47. City Heat (1984)
> Combined score: 0.99 — #19,083 highest out of 22,286 movies
> Director: Richard Benjamin
> Also starring: Burt Reynolds, Jane Alexander, Madeline Kahn
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.
46. The Rookie (1990)
> Combined score: 1.23 — #16,618 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Charlie Sheen, Raul Julia, Sônia Braga
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.
45. Any Which Way You Can (1980)
> Combined score: 1.26 — #16,184 highest out of 22,286 movies
> Director: Buddy Van Horn
> Also starring: Sondra Locke, Geoffrey Lewis, William Smith
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.
[in-text-ad-2]
44. Firefox (1982)
> Combined score: 1.39 — #14,646 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Freddie Jones, David Huffman, Warren Clarke
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.
43. Blood Work (2002)
> Combined score: 1.56 — #12,555 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Jeff Daniels, Anjelica Huston, Wanda De Jesus
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.
[in-text-ad]
42. Every Which Way but Loose (1978)
> Combined score: 1.59 — #12,163 highest out of 22,286 movies
> Director: James Fargo
> Also starring: Sondra Locke, Geoffrey Lewis, Beverly D’Angelo
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.
41. Paint Your Wagon (1969)
> Combined score: 1.61 — #11,868 highest out of 22,286 movies
> Director: Joshua Logan
> Also starring: Lee Marvin, Jean Seberg, Harve Presnell
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.
40. The Dead Pool (1988)
> Combined score: 1.62 — #11,838 highest out of 22,286 movies
> Director: Buddy Van Horn
> Also starring: Liam Neeson, Patricia Clarkson, Evan C. Kim
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.
[in-text-ad-2]
39. True Crime (1999)
> Combined score: 1.69 — #11,008 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Isaiah Washington, LisaGay Hamilton, James Woods
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.
38. Sudden Impact (1983)
> Combined score: 1.76 — #10,289 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Sondra Locke, Pat Hingle, Bradford Dillman
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.”
[in-text-ad]
37. Absolute Power (1997)
> Combined score: 1.77 — #10,264 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Gene Hackman, Ed Harris, Laura Linney
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.”
36. Cry Macho (2021)
> Combined score: 1.77 — #10,206 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Dwight Yoakam, Daniel V. Graulau, Amber Lynn Ashley
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.
35. Bronco Billy (1980)
> Combined score: 1.83 — #9,629 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Sondra Locke, Geoffrey Lewis, Scatman Crothers
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.
[in-text-ad-2]
33. Trouble with the Curve (2012)
> Combined score: 1.86 — #9,380 highest out of 22,286 movies
> Director: Robert Lorenz
> Also starring: Amy Adams, John Goodman, Justin Timberlake
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.
33. The Eiger Sanction (1975)
> Combined score: 1.86 — #9,380 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: George Kennedy, Vonetta McGee, Jack Cassidy
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.
[in-text-ad]
32. The Gauntlet (1977)
> Combined score: 1.93 — #8,729 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Sondra Locke, Pat Hingle, William Prince
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.
31. The Enforcer (1976)
> Combined score: 1.95 — #8,577 highest out of 22,286 movies
> Director: James Fargo
> Also starring: Tyne Daly, Harry Guardino, Bradford Dillman
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.
30. Space Cowboys (2000)
> Combined score: 1.96 — #8,439 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Tommy Lee Jones, Donald Sutherland, James Garner
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 “ââArmageddon” and “Deep Impact” and plays upon similar story tropes.
[in-text-ad-2]
29. Tightrope (1984)
> Combined score: 1.98 — #8,303 highest out of 22,286 movies
> Director: Richard Tuggle
> Also starring: Geneviève Bujold, Dan Hedaya, Alison Eastwood
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.
28. Joe Kidd (1972)
> Combined score: 1.99 — #8,162 highest out of 22,286 movies
> Director: John Sturges
> Also starring: Robert Duvall, John Saxon, Don Stroud
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.
[in-text-ad]
27. The Mule (2018)
> Combined score: 2.08 — #7,265 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Patrick L. Reyes, Cesar De León, Gustavo Muñoz
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.”
26. Coogan’s Bluff (1968)
> Combined score: 2.09 — #7,204 highest out of 22,286 movies
> Director: Don Siegel
> Also starring: Lee J. Cobb, Susan Clark, Tisha Sterling
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.
25. Heartbreak Ridge (1986)
> Combined score: 2.12 — #6,850 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Marsha Mason, Everett McGill, Moses Gunn
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.
[in-text-ad-2]
24. Two Mules for Sister Sara (1970)
> Combined score: 2.13 — #6,711 highest out of 22,286 movies
> Director: Don Siegel
> Also starring: Shirley MacLaine, Manolo Fábregas, Alberto Morin
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.
23. White Hunter Black Heart (1990)
> Combined score: 2.14 — #6,600 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Jeff Fahey, Charlotte Cornwell, Norman Lumsden
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.
[in-text-ad]
22. Magnum Force (1973)
> Combined score: 2.20 — #6,020 highest out of 22,286 movies
> Director: Ted Post
> Also starring: Hal Holbrook, Mitchell Ryan, David Soul
“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.
21. Honkytonk Man (1982)
> Combined score: 2.23 — #5,654 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Kyle Eastwood, John McIntire, Alexa Kenin
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.
20. Play Misty for Me (1971)
> Combined score: 2.27 — #5,159 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Jessica Walter, Donna Mills, John Larch
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.
[in-text-ad-2]
19. Thunderbolt and Lightfoot (1974)
> Combined score: 2.32 — #4,573 highest out of 22,286 movies
> Director: Michael Cimino
> Also starring: Jeff Bridges, George Kennedy, Geoffrey Lewis
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.
18. Hang ‘Em High (1968)
> Combined score: 2.36 — #4,064 highest out of 22,286 movies
> Director: Ted Post
> Also starring: Inger Stevens, Pat Hingle, Ed Begley
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.
[in-text-ad]
17. Mr. Warmth: The Don Rickles Project (2007)
> Combined score: 2.39 — #3,684 highest out of 22,286 movies
> Director: John Landis
> Also starring: Harry Dean Stanton, John Landis, Don Rickles
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.
16. A Perfect World (1993)
> Combined score: 2.40 — #3,529 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Kevin Costner, Laura Dern, T.J. Lowther
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.
15. Kelly’s Heroes (1970)
> Combined score: 2.45 — #3,002 highest out of 22,286 movies
> Director: Brian G. Hutton
> Also starring: Telly Savalas, Don Rickles, Carroll O’Connor
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.
[in-text-ad-2]
14. In the Line of Fire (1993)
> Combined score: 2.49 — #2,554 highest out of 22,286 movies
> Director: Wolfgang Petersen
> Also starring: John Malkovich, Rene Russo, Dylan McDermott
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.
13. Pale Rider (1985)
> Combined score: 2.51 — #2,316 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Michael Moriarty, Carrie Snodgress, Sydney Penny
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.
[in-text-ad]
12. Where Eagles Dare (1968)
> Combined score: 2.55 — #1,870 highest out of 22,286 movies
> Director: Brian G. Hutton
> Also starring: Richard Burton, Mary Ure, Patrick Wymark
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.”
11. The Bridges of Madison County (1995)
> Combined score: 2.56 — #1,768 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Meryl Streep, Annie Corley, Victor Slezak
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.
10. Gran Torino (2008)
> Combined score: 2.56 — #1,735 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Bee Vang, Christopher Carley, Ahney Her
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.
[in-text-ad-2]
9. High Plains Drifter (1973)
> Combined score: 2.57 — #1,677 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Verna Bloom, Marianna Hill, Mitchell Ryan
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.
8. Dirty Harry (1971)
> Combined score: 2.57 — #1,622 highest out of 22,286 movies
> Director: Don Siegel
> Also starring: Andrew Robinson, Harry Guardino, Reni Santoni
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.
[in-text-ad]
7. Escape from Alcatraz (1979)
> Combined score: 2.60 — #1,324 highest out of 22,286 movies
> Director: Don Siegel
> Also starring: Patrick McGoohan, Roberts Blossom, Jack Thibeau
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.
6. The Outlaw Josey Wales (1976)
> Combined score: 2.63 — #979 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Sondra Locke, Chief Dan George, Bill McKinney
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.
5. Million Dollar Baby (2004)
> Combined score: 2.65 — #850 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Hilary Swank, Morgan Freeman, Jay Baruchel
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.
[in-text-ad-2]
4. For a Few Dollars More (1965)
> Combined score: 2.72 — #357 highest out of 22,286 movies
> Director: Sergio Leone
> Also starring: Lee Van Cleef, Gian Maria Volonté, Mara Krupp
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.
3. A Fistful of Dollars (1964)
> Combined score: 2.73 — #321 highest out of 22,286 movies
> Director: Sergio Leone
> Also starring: Gian Maria Volonté, Marianne Koch, Wolfgang Lukschy
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.
[in-text-ad]
2. Unforgiven (1992)
> Combined score: 2.75 — #198 highest out of 22,286 movies
> Director: Clint Eastwood
> Also starring: Gene Hackman, Morgan Freeman, Richard Harris
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.
1. The Good, the Bad and the Ugly (1966)
> Combined score: 2.88 — #12 highest out of 22,286 movies
> Director: Sergio Leone
> Also starring: Eli Wallach, Lee Van Cleef, Aldo Giuffrè
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.
Thank you for reading! Have some feedback for us?
Contact the 24/7 Wall St. editorial team.