An iconic actor and an indelible part of both Hollywood history and the public perception of the Western genre, Clint Eastwood has achieved just as much behind the camera as he has in front of it. His films as a director have pushed boundaries, defied expectations, conquered the box office, and won him numerous awards.
He remains to this day a difficult voice to pin down. Sometimes traditional, sometimes remarkably subversive, Eastwood always has something to say, and his films are rarely dull to watch. Here are his ten best films as director, according to the rankings of review aggregate site Rotten Tomatoes.
White Hunter Black Heart (88%)
Though often thought of for his strikingly original Westerns or his latter day true stories, Clint Eastwood has had a very successful career as a director with straight literary adaptations. The first of many on this list is an adaptation of Peter Viertel’s novel of the same name. It revolves around a thinly-veiled retelling of Viertel’s experiences on the making of John Huston’s classic film The African Queen.
Eastwood himself stars as the story’s Huston proxy, John Wilson, and, whilst still always Clint Eastwood first and foremost, he does a very good job of impersonating the famous director and his theatrical mannerisms.
Mystic River (88%)
An adaptation of renowned crime writer Dennis Lehane’s novel of the same name, Mystic River is a mystery film based around a group of distinct characters with vastly complex personal histories. The story concerns the murder of a young girl, with three childhood friends – on varying sides of the law – all deeply invested in the case.
A gripping and thrilling drama, the film was nominated for six Oscars in major categories, winning Best Actor for Sean Penn and Best Supporting Actor for Tim Robbins.
The Bridges Of Madison County (90%)
Based on Robert James Waller’s novel of the same name, The Bridges of Madison County is a film that takes its time in telling a simple love story and its unhurried pace may be its best quality. No mean feat in a film sporting charismatic and compelling lead performances from both Eastwood and Meryl Streep.
Fans of romantic weepies like The Notebook will appreciate its unapologetic sentimentality and fans of understated tour de forces will appreciate Streep’s Oscar-nominated performance.
Million Dollar Baby (91%)
Eastwood was nominated for Best Actor for his role as tough-but-fair boxing coach Frankie Dunn in Million Dollar Baby. He didn’t win, but Eastwood’s directing skills were completely vindicated with wins for Hillary Swank for Best Actress, Morgan Freeman for Best Supporting Actor, Best Director and Best Picture.
Million Dollar Baby is a great example of how, even when taking a lead role, Eastwood can appear to be the least important presence in some of his greatest films. Instead, he provokes the best from the entire ensemble while tying all of their characters together.
Letters From Iwo Jima (91%)
The second part of Eastwood’s double bill of WW2 movies, Letters from Iwo Jima presents the Japanese perspective of the fight for the titular island. Like the previous film from the duo, showing the American perspective of the battle, it removes many of the frills traditional to war movies for a more revisionist approach.
It faired much better overall compared to companion piece Flags of Our Fathers and was nominated for four Oscars, including Best Picture and Best Director for Eastwood.
The Outlaw Josey Wales (92%)
The first of Eastwood’s numerous Westerns on this list is an important stepping stone between the shifting phases of his image. Known the world over as Sergio Leone’s “The Man With No Name”, Eastwood’s grimace and steely resolve had become archetypical for the genre. The Outlaw Josey Wales began a long road of Eastwood re-examining, and toying with, this image.
The Civil War Western was his second film in the genre as a director and a sprawling, varied, adventure story that lived up to Leone’s final masterwork with Eastwood, The Good, the Bad and the Ugly.
Pale Rider (92%)
Eastwood’s third Western as a director was a lot like his first. Pale Rider applied a thick layer of unmistakable horror to the tropes of the Western genre for a memorable result. Eastwood plays the mysterious Preacher figure at the center of the story, showing up in a small mining community to dispense violent justice to the thugs harassing the local miners and the greedy business interests controlling them.
A lot like Sergio Corbucci’s cult classic Western The Great Silence, but played as the straight Hollywood Western that Corbucci was attempting to subvert, Pale Rider is as grim as its namesake but hugely entertaining also.
Honkytonk Man (93%)
Eastwood isn’t all serious drama and bloody violence. The highest-rated of his more comedic efforts follows a young boy in the Great Depression as he becomes the driver and partner-in-crime of his guitar-playing ne'er do well uncle (played by Eastwood).
A coming-of-age story in many ways as well as an episodic comedy adventure in the vein of Mark Twain, Honkytonk Man was another triumph of literary adaptation for Eastwood as a director. It also showcases Eastwood’s often-overlooked love of music, with some great songs sung by the man himself throughout the film.
Unforgiven (96%)
Dedicated to his two great cinematic collaborators and mentors, directors Don Siegel and Sergio Leone, Unforgiven is a culmination of both Eastwood’s star persona from the Western genre and his direct commentary on it. Though his following films would be influenced by the genre, it would be Eastwood’s last out-and-out Western and arguably the last truly significant entry in their development to date. It’s currently the last film in the genre to win Best Picture, barring the Coen Brothers’ No Country for Old Men (if you count it as a Western).
Eastwood’s portrayal of aging outlaw Wiliam Munny would earn him much acclaim, but the film is mostly remembered as a directing triumph and finally won him Best Director at the Oscars (for the first time).
High Plains Drifter (96%)
High Plains Drifter was Eastwood’s second film as a director and his first Western in that role. Like the others, he would take the lead role and, like Pale Rider, the film could easily be interpreted as a horror movie. Both the strangeness of the semi-supernatural story and Dee Barton’s often-eerie score make it a unique flavor of Western, clearly influenced by Eastwood’s time in the Italian Spaghetti Western scene.
It follows an increasingly bizarre vengeance that’s visited upon a lakeside town following a murder that brings collective shame to the townsfolk. It’s a great early film from Eastwood to check out if you have an impression of him being boring and want to challenge that image.