7 best movies directed by Clint Eastwood, ranked

It’s rare for a top movie star to step behind the camera and thrive critically and financially as a director. From the 1930s through the 1960s, Orson Welles and Charlie Chaplin were the gold standards for actors-turned-directors. But since the 1970s, good luck finding a more successful actor-director than Clint Eastwood. The actor was already a star in the early 1970s thanks to his roles in Sergio Leone’s Dollars Trilogy and Dirty Harry.

Eastwood directed his first film in 1971 with Play Misty for Me. Since then, he has directed nearly 40 films, from Westerns and crime thrillers to Oscar winners and war epics. Known for his efficiency (“One Take Clint“), Eastwood is still directing in his early 90s, with his next film, Juror No. 2, expected to release in 2024. To honor this great American filmmaker, we ranked his seven best films as a director.

7. Gran Torino (2008)

Retired autoworker and Korean War veteran Walt Kowalski (Eastwood) hates what has become of America. Walt despises the influx of Hmong immigrants that have moved into his Detroit neighborhood and the gang violence that has a stranglehold over its residents. Thao Vang Lor (Bee Vang), ateenager who lives next door to Walt, attempts to steal Walt’s Gran Torino, but fails. Instead of reporting the boy to the police, Walt surprisingly forms a friendship with Thao as he tries to straighten him out and put him on the right course in life.

Gran Torino is in the running for Eastwood’s best acting of the 21st century. With the film, Eastwood attempts to explain that America is for everyone through Walt’s prejudiced persona — and it mostly works. Gran Torino has also been praised for its predominantly Hmong-American cast, a first among mainstream American films.

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6. The Outlaw Josey Wales (1976)

Before 1976, Eastwood had directed four films. However, Eastwood’s fifth film, The Outlaw Josey Wales, is the moment where his directorial career took off. After Union soldiers led by Capt. Terrill (Bill McKinney) kill his family, Josey Wales (Eastwood) joins the Confederate Army and teams with guerrilla fighters to exact his revenge. Josey becomes a legendary gunfighter and refuses to surrender when the war ends. With a bounty on his head, Josey tries to start over with a surrogate family, but his history as an outlaw endangers those around him.

Like many of his films, Eastwood thrives as a vengeful rebel, but his humanization of Native Americans is the lasting memory in this terrific Western. The Outlaw Josey Wales is also noteworthy for its behind-the-scenes drama between Eastwood and the film’s original director, Philip Kaufman. Eastwood fired Kaufman during production and took over as the director, leading the Directors Guild of America to create “The Eastwood Rule,” which forbids an actor or producer from firing a director and taking over the production themselves.

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5. Letters from Iwo Jima (2006)

In 2006, Clint Eastwood made two war movies about the iconic Battle of Iwo Jima in World War II: Flags of Our Fathers and Letters from Iwo Jima. Released in October 2006, Flags of Our Fathers is told from the American viewpoint and chronicles the lives of the soldiers who fought to raise the flag in one of WWII’s most iconic moments.

Two months later, Eastwood released the superior film, Letters from Iwo Jima, which depicts the battle from the perspective of several Japanese soldiers, including General Tadamichi Kuribayashi (Ken Watanabe). Despite being an American filmmaker, Eastwood does right by the Japanese soldiers, showing that war is hell for all parties.

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4. The Bridges of Madison County (1995)

I believe it’s fair to say Eastwood isn’t exactly “Mr. Romance.” Most of the roles he plays are outlaws, action heroes, or conflicted men who turn to violence to cope with their problems. In a surprise move, Eastwood traded his gun for a camera in The Bridges of Madison County. Based on Robert James Waller’s bestselling novel, The Bridges of Madison County stars Only Murders in the Building’s Meryl Streep as Francesca Johnson, an Italian war bride living with her husband and two children in Iowa in 1965. When her family attends the state fair, Francesca stays home. She meets National Geographic photographer Robert Kincaid (Clint Eastwood), who shows up at her doorstep asking for directions to Roseman Bridge.

Over the next four days, Francesca and Robert engage in a love affair that reignites their passions in life. Streep is good in everything, so she unsurprisingly excels as a woman stuck between love and responsibility. However, Eastwood’s performance is the standout, considering how much of a left turn this role was for him. It makes you wish he had directed and starred in more romantic dramas.

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3. Million Dollar Baby (2004)

Million Dollar Baby isn’t exactly the most rewatchable movie due to the sad tragedy near the end. However, that doesn’t take away from its standing as an entertaining and great film. Aspiring boxer Maggie Fitzgerald (Hilary) wants to be coached by the hardened boxing trainer Frankie Dunn (Clint Eastwood). Frankie says he doesn’t train women, but that doesn’t stop Maggie from showing up at his Los Angeles gym.

Eventually, Frankie agrees to train Maggie, who quickly shows promise. Frank, an estranged father, and Maggie, a black sheep in her family, form a special bond as their friendship extends outside the ring. This boxing movie can be gut-wrenching, but its messages about pain, loss, and perseverance will stick with you long after it ends. Million Dollar Baby led to Eastwood’s second Oscar for Best Director and additional wins for Best Picture, Best Actress (Swank), and Best Supporting Actor (Morgan Freeman).

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2. Mystic River (2003)

Out of his directed films, Mystic River, a 2003 crime drama based on the novel by Dennis Lehane, features the best cast. Sean Penn, Tim Robbins, Kevin Bacon, Laurence Fishburne, Laura Linney, and Marcia Gay Harden all give some of the best performances of their careers in Mystic River. Ex-con Jimmy Markum (Penn), detective Sean Devine (Bacon), and blue-collar worker Dave Boyle (Robbins) have known each other since they were kids growing up in Boston in the 1970s.

After Jimmy’s daughter Katie (Emmy Rossum) is killed, Dave, who has lived with years of grief after being kidnapped and molested as a child, becomes a suspect. Jimmy wants revenge for his daughter’s death and conducts his own investigation, while Sean races to find the killer before his childhood friend does. Mystic River is a harrowing film because of its grim themes – child abuse, murder, and violence. However, it’s also an arresting examination of the past and the difficulties of living with childhood trauma.

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1. Unforgiven (1992)

In the town of Big Whiskey, Wyoming, a group of prostitutes put a bounty on a group of cowboys after one of them disfigures one of their own, Delilah Fitzgerald (Anna Thomson). The bounty attracts several bounty hunters to Big Whiskey, including the weathered ex-bandit William Munny (Clint Eastwood), who leads a team with his old partner Ned Logan (Morgan Freeman) and “The Schofield Kid” (Jaimz Woolvett). The presence of the bounty hunters in Big Whiskey irks Sheriff Little Bill Daggett (Gene Hackman), who runs the town with an iron fist. The town is too big for Will and Little Bill, leading to an epic showdown between the two alphas. 

Unforgiven is a fascinating mediation on morality, forgiveness, and redemption. Backed by sensational performances from the cast, Unforgiven is Eastwood’s best-directed movie. The Academy agreed, too, considering they awarded the Western with four Oscars: Best Picture, Best Director, Best Supporting Actor (Hackman), and Best Film Editing. 

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