Clint Eastwood, the actor-turned-director and producer, has had one of the longest and most varied careers of anyone working in the entertainment world. In addition to his film work he has also amassed an impressive resume as a musician and composer and even served as the mayor of the California town Carmel-by-the-Sea during the 1980s.
Eastwood began his film career in westerns and later also found success in crime dramas. He was mostly known for his striking good looks and stoic demeanor though and was not really considered a serious or talented actor. He would slowly work to change that fact and would eventually receive two Oscar nominations for his acting, both as Best Actor for “Unforgiven” in 1992 and “Million Dollar Baby” in 2004. While he didn’t win either of those acting awards, he would win two Oscars for each of those films as Best Director and as a producer when they each won Best Picture. In total Eastwood would receive 11 Oscar nominations as in the categories of either Best Picture, Director or Actor. He also received the 1995 Irving Thalberg Award from the Academy, plus the Cecil B. DeMille Award, SAG life achievement award, AFI life achievement award and Kennedy Center Honors.
Many actors embark on careers as directors but usually their success and options are limited only to films in which they also appear. Eastwood has done his fair share of that but he also has found great success in films with which he didn’t appear as an actor. He has directed a surprising 39 films throughout his career with many of his cast members receiving Oscar nominations. He has directed Gene Hackman (“Unforgiven”), Hilary Swank and Morgan Freeman (“Million Dollar Baby”) and Sean Penn and Tim Robbins (“Mystic River”) to acting victories at the Oscars. His latest was “Cry Macho,” which opened September 17, 2021.
Take a tour in our photo gallery to see our choices of his 20 greatest film performances as an actor (not as a director or producer), ranked from worst to best. Our list includes his Oscar-nominated roles, plus “The Good, The Bad and The Ugly,” “Dirty Harry,” “The Bridges of Madison County,” “The Outlaw Josey Wales” and more. You can also tour our gallery ranking his best movies as a director.
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20. TWO MULES FOR SISTER SARA (1970)
Image Credit: Courtesy of Universal Pictures Director: Don Siegel. Writer: Albert Maltz. Starring Shirley MacLaine.
Eastwood has wonderful chemistry with Shirley MacLaine in this comedic western. Eastwood meets MacLaine when he saves her from being attacked by a gang of men. He is then shocked to find out the sexy naked woman he saved is actually a nun. (Or is she?) MacLaine’s wonderful deadpan delivery as she spins a false tale for Eastwood and his awkward reactions to her are priceless.
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19. SUDDEN IMPACT (1983)
Image Credit: Courtesy of Warner Bros. Director: Clint Eastwood. Writer: Joseph Stinson. Starring Sondra Locke, Pat Hingle, Bradford Dillman.
“Sudden Impact” was the fourth film in the Dirty Harry series and the only one Eastwood directed himself in. The film wasn’t the most acclaimed of the series and received a fair share of negative reviews. While the story and film itself is a bit lurid the film did find a place in film history by providing one of the most famous movie quotes ever with Eastwoods delivery of go ahead, make my day.
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18. THUNDERBOLT AND LIGHTFOOT (1974)
Image Credit: Courtesy of United Artists Director and writer: Michael Cimino. Starring Jeff Bridges, Geoffrey Lewis, Gary Busey.
Eastwood plays the grizzled veteran robber while Jeff Bridges plays a quirky young partner Eastwood begins to work with. Bridges was a surprise nominee for Best Supporting Actor considering the genre of the film but his combination of youthful energy and offbeat comedic charm clearly made an impression on voters. He lost the Oscar though to Robert De Niro for “The Godfather Part II.
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17. GRAN TORINO (2008)
Image Credit: Anthony Michael Rivetti Director: Clint Eastwood. Writer: Nick Schenk. Starring Bee Vang, Ahney Her, Christopher Carley.
Eastwood gave an acclaimed performance in this film he also directed. The story centers on an elderly man who just lost his wife of 50 years. He feels alone and isolated in his community of a Detroit suburb which has changed over time with the exit of factory workers and the influx of poor Asian immigrants. His life changes though through a connection with one of his new neighbors. Eastwood seemed to be a possible Best Actor Oscar contender early in the race since he won the National Board of Review Best Actor Award and was a runner up for the New York and National Society critics circle awards but he failed to make the cut at Oscar nomination time.
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16. TIGHTROPE (1984)
Image Credit: Courtesy of Warner Bros. Director and writer: Richard Tuggle. Starring
Geneviève Bujold, Dan Hedaya, Allison Eastwood.Clint Eastwoods early career never really got him much attention when it came to Oscars and other award shows. His early westerns and genre pictures didn’t really deliver the kind of performances that earned nominations. That would eventually change later in his career. This film though was the first time that Eastwood actually managed to generate some Oscar buzz for a performance. Eastwood plays a detective tracking a serial rapist and killer who finds himself being taunted by the killer. Geneviève Bujold also gave an acclaimed performance as a rape crisis counselor and was considered a possible Best Supporting Actress nominee although the film ultimately didn’t earn any Oscar notice.
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15. THE EIGER SANCTION (1975)
Image Credit: Courtesy of Universal Pictures Director: Clint Eastwood. Writers: Hal Dresner, Warren Murphy, Rod Whitaker. Starring George Kennedy, Vonetta McGee, Jack Cassidy.
Eastwood directed himself in this thriller that features incredible mountain climbing scenes on the Eiger, a mountain in the Swiss Alps. He plays an art professor and collector who also just happens to be a paid assassin. He has tried to leave his assassin past behind him but the government calls him back for two more sanctions, which means two more killings.
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14. IN THE LINE OF FIRE (1993)
Image Credit: Columbia Pictures Director: Wolfgang Peterson. Writer: Jeff Maguire. Starring John Malkovitch, Rene Russo, Dylan McDermott.
This highly exciting film from “Das Boot” director Wolfgang Peterson casts Eastwood as a Secret Service agent who was on duty the day JFK was assassinated. He is determined not to let the current president fall victim to a sinister killer who is threatening the president. John Malkovitch had a scene stealing role as the killer and earned Best Supporting Actor nominations at the Oscars, Golden Globes, and BAFTA. He would lose the Oscar though to Tommy Lee Jones for The Fugitive.
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13. THE BEGUILED (1971)
Image Credit: Courtesy of Universal Pictures Director: Don Siegel. Writer: Albert Maltz, Irene Camp. Starring Geraldine Page, Elizabeth Hartman, Pamelyn Ferdin.
This gothic psychological thriller features Eastwood as a union soldier during the American civil war who is imprisoned in a confederate girls boarding school. Geraldine Page magnificently plays the repressed head of the school who decides to keep Eastwood locked away. Eastwood begins to ignite sexual feelings among all the women at the school which leads to disastrous results. Sofia Coppola recently remade the film with Nicole Kidman and Colin Farrell to much less successful results.
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12. COOGAN’S BLUFF (1968)
Image Credit: Courtesy of Universal Pictures Director: Don Siegel. Writers: Herman Miller, Dean Riesner, Howard Rodman. Starring Lee J. Cobb, Susan Clark, Don Stroud.
It was a while into his career before Eastwood began to be regarded as a serious actor with range. The smart thing he did while he was still learning the ropes was to surround himself with more versatile actors with emotional ranges larger than Eastwood’s. As with Geraldine Page in “The Beguiled” here he is paired with the great Lee J. Cobb and the two lift the film from its genre roots. Eastwood plays an Arizona police detective in New York to bring back an escaped convict.
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11. HIGH PLAINS DRIFTER (1973)
Image Credit: Courtesy of Universal Pictures Director: Clint Eastwood. Writer: Ernest Tidyman. Starring Verna Bloom, Mitchell Ryan, Stefan Gierasch.
“High Plains Drifter” was the first western film Eastwood directed. Eastwood brings dry humor to this story of a gunfighter and drifter who helps a small town band together to fight off three outlaw gunmen who are on their way to the town.
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10. THE BRIDGES OF MADISON COUNTY (1995)
Image Credit: Courtesy Image Director: Clint Eastwood. Writer: Richard LaGravenese. Starring Meryl Streep, Annie Corley, Victor Slezak.
Eastwood directed and starred in this adaptation of the best-selling novel about a photographer photographing covered bridges who meets and has a brief affair with an Iowa farmwife. This is one of Eastwood’s most vulnerable and sensitive performances. Some critics described him as seeming a bit intimidated by Meryl Streep and all of her famed artistry but that actually works for the film since Eastwood’s perhaps real life insecurity working with the legendary actress carries over to the character who is a bit intimidated and awkward with the intensity the woman loves him and his inability to express it in return.
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9. FOR A FEW DOLLARS MORE (1965)
Image Credit: Courtesy of United Artists Director: Sergio Leone. Writers: Luciano Vincenzoni, Sergio Leone. Starring Lee Van Cleef, Klaus Kinski, Gian Maria Volontè.
This is the second film in thedollars trilogy which were all directed by Sergio Leone and introduced movie audiences to Eastwood who had previously made his living on television. Eastwood stars with Lee Van Cleef as two bounty hunters who are both tracking the same man so they decide to team up. A British journalist named Kim Newman made an interesting point with the observation that the film changed the way bounty hunters were viewed by audiences. It moved them away from a “profession to be ashamed of”, one with a “(ranking) lower than a card sharp on the Western scale of worthwhile citizens”, to one of heroic respectability.
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8. HANG ‘EM HIGH (1968)
Image Credit: Courtesy of United Artists Director: Ted Post. Writer: Leonard Freeman, Mel Goldberg. Starring Inger Stevens, Ed Begley, Ben Johnson.
This was Eastwoods first starring role in a western that wasn’t directed by Sergio Leone and the first one that he produced with his own production company. Eastwood plays a man who is mistaken from for a cattle rustler and nearly lynched when he is hanged from a tree. He survives the incident and then is offered a law enforcement job and sets out to bring the men who nearly killed him to justice. The excellent supporting cast features two Oscar winners for Best Supporting Actor, Ed Begley (who won for the “Sweet Bird of Youth” in 1962) and Ben Johnson (winner in 1971 for “The Last Picture Show”)
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7. A FISTFUL OF DOLLARS (1964)
Image Credit: Courtesy of Unidis Director: Sergio Leone. Writers: Víctor Andrés Catena, Jaime Comas Gil, Sergio Leone. Starring Marianne Koch, Gian Maria Volontè, Wolfgang Lukschy.
Eastwood first starring role in a film came in this, the first film of the “dollars” series and his first collaboration with Sergio Leone. The movie launched the genre that became known as the spaghetti westerns meaning they were films about the American west directed by an Italian director. The films violence mixed with its somewhat campy humor confused a lot of critics at the time and reviews were decidedly mixed. One fan of the film though is Quentin Tarantino who described the film as “the greatest achievement in the history of Cinema” in a press release for the films 50th anniversary screening at the Cannes film festival.
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6. PLAY MISTY FOR ME (1971)
Image Credit: Courtesy Image Director: Clint Eastwood. Writers: Jo Heims, Dean Riesner. Starring Jessica Walter, Donna Mills, Clarice Taylor.
Eastwood scored big time with his first outing as a director in this superb thriller. He plays an overnight radio disc jockey at a jazz station who becomes intrigued by a female caller who frequently phones the station asking if he’d play misty for me. He then meets the woman in a bar, has a one-night stand with her and then is terrorized by the woman’s increasingly clingy and violent behavior. You could say that the woman develops a “fatal attraction” toward Eastwood since the plot of this film and the 1987 blockbuster “Fatal Attraction” starring Michael Douglas and Glenn Close have remarkably similar plots. (Eastwood has said they basically remade his film with out giving this film any credit.) Eastwood is wonderfully matched by the superb Jessica Walter as the obsessed fan. She earned a Best Actress in a Motion Picture Drama Golden Globe nomination and should have been nominated for an Oscar but was inexplicably left out.
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5. THE OUTLAW JOSEY WALES (1976)
Image Credit: Courtesy of Warner Bros. Director: Clint Eastwood. Writers: Philip Kaufman, Sonia Chernus. Starring Chief Dan George, Sondra Locke, Sam Bottoms.
Eastwood directed and stars in this western with a much darker tone and edge than the spaghetti westerns that made him a movie star. He plays a farmer whose family is murdered by militant union soldiers in the American civil war. To seek vengeance, he joins with the confederate army but when the war ends and his confederate comrades are all murdered upon their surrender, he goes it on his own to fight his pursuers.
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4. DIRTY HARRY (1971)
Image Credit: Courtesy Image Director: Don Siegel. Writers: Harry Julian Fink, Rita M. Fink, Dean Riesner. Starring Harry Guardino, John Vernon, Andrew Robinson.
Eastwood found one of his signature roles in this film as Harry Callahan a relentless San Francisco police inspector on the trail of a psycho serial killer. The film would spawn four sequels. This bit of dialogue when Harry stares down a punkbecame one of the most famous bits of dialogue in movie history: “Uh uh. I know what you’re thinking.” “Did he fire six shots or only five?” Well to tell you the truth in all this excitement I kinda lost track myself. But being this is a .44 Magnum, the most powerful handgun in the world and would blow your head clean off, you’ve gotta ask yourself one question: “Do I feel lucky?” “Well, do ya, punk?”
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3. THE GOOD, THE BAD AND THE UGLY (1966)
Image Credit: Courtesy of Produzioni Europee Associate Director: Sergio Leone. Writers: Agenore Incrocci, Furio Scarpelli, Luciano Vincenzoni, Sergio Leone. Starring Eli Wallach, Lee Van Cleef, Luigi Pistilli.
Eastwood once again teamed with Sergio Leoni for a spaghetti western. This their third outing proved one of their most popular pairings. Eastwood is joined again by Lee Van Cleef and this time also co-stars with Eli Wallach in a very popular performance as The Rat, a fast-talking Mexican bandit. The film’s reputation grew as the years passed. Roger Ebert admitted he initially only gave the film three stars because he felt spaghetti westerns were looked down on but in later years, he would revise his opinion of the quality of the film.
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2. MILLION DOLLAR BABY (2004)
Image Credit: Merie W. Wallace Director: Clint Eastwood. Writer: Paul Haggis. Starring Hilary Swank, Morgan Freeman, Jay Baruchel.
“Million Dollar Baby” was perhaps the most acclaimed movie of 2004. It received seven Oscar nominations and won the awards for Best Picture, Best Director for Eastwood, Best Actress for Hilary Swank, and Best Supporting Actor for Morgan Freeman. Eastwood was also nominated as Best Actor but he lost that award to Jamie Foxx in “Ray” The film tells the story of a young woman who aspires to be a professional boxer. She forms a deep bond with her trainer (Eastwood) that takes them through both triumph and tragedy.
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1. UNFORGIVEN (1992)
Image Credit: Courtesy Image Director: Clint Eastwood. Writer: David Webb Peoples. Starring Gene Hackman, Morgan Freeman, Richard Harris.
“Unforgiven” was widely seen as the culmination of all that Eastwood had learned doing westerns over the years. He dedicated the film to his mentors directors Sergio Leone and Don Siegel. The film took a more serious look at the violence often portrayed in westerns and Eastwood wanted to show the human toll such violence takes on people. Appropriately Eastwood plays a gunslinger who comes out of retirement for one last job. It was nominated for 9 Oscars and won four of them: Best Picture, Best Director for Eastwood, Best Supporting Actor for Gene Hackman’s villainous sheriff and Best Film Editing. Eastwood was also once again nominated for Best Actor but lost that award to Al Pacino for “Scent of a Woman.”
