What makes Clint Eastwood a special Hollywood specimen is that he’s as revered as one of the great American directors of his generation as he’s beloved for being one of its most indelible movie stars. Managing to maintain those legendary statuses hand in hand is a crowning achievement, even if his versatile and prolific work over the last six decades has yielded as many duds as classics. With his maybe jingoistic (or is it?) The 15:17 to Paris, his 40-something-th film, currently in theaters—racking up quite a mountain of rotten ratings on Rotten Tomatoes at that—we thought we’d remind you of some of Eastwood’s best work as a director, some genuine masterpieces tucked in here and there.
When he was starting out as a director, Eastwood took a great deal of inspiration from the two most influential filmmakers for whom he’d worked: Sergio Leone and Don Siegel. He adapted the meticulous framing—with great attention to both foreground and background depth—perfected by Leone, especially as he made his way towards helming westerns. But when it come to a quick and decisive work ethic, especially for his directorial debut, mimicking Siegel’s efficiency-based approach, focusing only on the base needs of each scene, doing two or three takes and moving on, allowed him to deliver the kind of instant and unpredictable intensity that this terrific thriller needed. Play Misty for Me is about an unhinged woman (Jessica Walter, somehow scarier here than in Arrested Development) who takes her obsession with a local radio DJ (Eastwood) to dangerous levels, potentially laying the foundation for Single White Female and countless ’90s psycho girlfriend/boyfriend/roommate movies to come.
On paper, there isn’t much to John Lee Hancock’s screenplay about a seasoned criminal named Butch (Kevin Costner) escaping prison, kidnapping Philip (T.J. Lowther)—a melancholic kid who’s raised without any of the fun that comes with childhood because he’s part of a strict Jehovah’s Witness family—to use him as a hostage as he drives for the border. The narrative and character beats hit exactly when they’re supposed to: Butch and Philip eventually form a bond; Butch helps Philip enjoy life; Philip’s innocence pushes Butch to become a better person until, of course, the law catches up to them and a standoff ensues. What makes A Perfect World still so gripping is Eastwood’s delicate, nostalgic use of the Texas countryside, as well as the natural performances he extracts out of Costner and the child actor, who themselves have a palpable. Costner was at the height of his stardom at the time, known for playing morally airtight do-gooders, so this antihero was a risky move on his part, playing a dark, violent character who can become an imperfect but necessary father figure.
Apart from a disgusting rape scene that’s completely unnecessary to the flow of the story, High Plains Drifter still counts as a unique genre-stretching exercise, and one of Eastwood’s most tonally playful films. Essentially a supernatural thriller hidden inside a thick, old-fashioned western coating, High Plains Drifter sees Eastwood cleverly deciding not to play it safe when it comes to directing his first attempt at the genre that turned him into an international megastar. The film begins the way any of Leone’s Man With No Name movies could have, as a supposedly roaming stranger who’s an expert in killing, and looking cool while doing it (Eastwood), shows up at a troubled town in the middle of nowhere and systematically cleanses it of murderous criminals. Sounds pretty cut and dry, until some surreal elements begin to sneak into the picture, accompanied by the deliberate build-up of suspense, turning this simple premise into a downright biblical tale of divine vengeance.
If you’re in the mood for a superb classic western—looking for a satisfying combo of the morbid whimsy found in Leone’s work and the wholesome, adventure-heavy John Ford style—then The Outlaw Josey Wales should deliver on this compromise. Eastwood sensed the popularity of the traditional western was on its way out when Josey Wales went into production, so he composed a fitting Swan Song for the genre. It’s a messy proposition, but what we get is an epic genre exercise that seldom loses our attention, mostly due to the intense narrative focus Eastwood carried over from his work with Don Siegel. Eastwood is predictably badass in the title role, but the MVP of the picture is his no-nonsense sidekick played by the illustrious Chief Dan George. (For more of George’s natural charisma, check out Little Big Man.)
Though he’s primarily known for helming male-oriented tales dripping with machismo, Eastwood has a tender, smooth operator side that will hopefully emerge again soon. His third film as a director was the underrated Breezy, a surprisingly even-handed romance between a young hippie and a jaded middle-aged man. Decades later, Eastwood tried his hand at another romance property, this time the widely anticipated adaptation of Robert James Waller’s bestselling novel, about a lonely married woman (Meryl Streep) falling in love with a smoldering photographer (Eastwood), their quick fling spiraling into a whirlwind affair. Will she leave her comfortable and responsible life behind to go on an adventure with the photographer, or is it too late for her? By focusing on the universal feelings every audience would have with vital choices they had to make in their lives, some of them propelled by undeniably strong emotions, Eastwood transcends the confines of the tear-jerker melodrama, supported heavily by the sometimes tumultuous, sometimes wistful performances of his two leads.
Eastwood has never been shy about expressing his Republican views, yet he used to be more in tune with inserting more positive conservative ideals—personal responsibility, zero tolerance against violent crime, the protection of one’s property—into his work, rather than simple-minded or destructive mores. Gran Torino, a stern but compassionate drama about a racist, lonely old man (Eastwood in his last great role so far) in Detroit who befriends a Hmong family and uses his last bit of strength to protect them from rampant gang violence, is one of Eastwood’s films that errs toward the “good” side of his ideological spectrum. In many ways, one can look at Eastwood’s character in Gran Torino as an extension of Harry Callahan: a grumpy loner with the soul of Wild West vigilantism. Perhaps as a rebuttal to Callahan’s violent tendencies, his philosophy to shoot first and ask questions later, Eastwood ends Gran Torino with a surprisingly pacifist solution.
Mystic River is ostensibly a Boston-based whodunit thriller about the mystery surrounding the sudden murder of a local mob boss’s (Sean Penn, who delivers one of the most heartbreaking monologues of the ’00s) daughter. However, the genre machinations are just the cherry on top of this somber and sobering drama about how time eventually embitters us all, and how desperation and paranoia can turn us into monsters. The broken bond between the three childhood friends (Penn, Tim Robbins, Kevin Bacon) at the center of Brian Helgeland’s airtight adaptation of Dennis Lehane’s novel is pushed to the limits when Penn’s character begins to suspect one of his buddies, a suspicion made complicated by a traumatic choice they made as children. As the narrative sprawls, Eastwood keeps a consistent tone, never getting in the way of the performances of his three leads, which, alongside the always reliable Marcia Gay Harden, are tops.
Though the backlash against Million Dollar Baby began almost immediately after it won the Oscar for Best Picture—did it win only because of the controversial ending? was it too schmaltzy and manipulative?—a decade since its release and what we have today is a spectacularly effective Melodrama (capital “M”) that’s never ashamed of its genre. The dark and uncomfortable places the story goes, of a female boxer (Hilary Swank) rising up in the ranks through a cranky coach’s (Eastwood) training, is supported by the strong bond that’s established between the two protagonists. With hard-earned emotional stakes, Eastwood swoops in and delivers a devastating gut punch.
After winning his second Oscar for Best Picture, Eastwood teamed up with another legendary Hollywood director, Steven Spielberg, to deliver a bittersweet love letter to World War II troops with a story about the aftermath of the Battle of Iwo Jima. But all the research for Flags of Our Fathers persuades Eastwood to tell the Japanese side of the story, to give the American film a smaller sister piece—which happens to be not only one of the most outstanding works of his career, but one of the great Japanese war films ever made. Perhaps because he was unburdened by the ability to make a film that’s not about his countrymen, Eastwood presents a refreshingly non-political look at warfare, in which the human toll takes the center stage, brave patriots turn into useless tools of destruction, and cowards and “bleeding hearts” arbitrarily come across grace and beauty inside the chaos of the conflict. It’s shocking to think a masterwork this astute and thoughtful came from the same mind that made American Sniper just eight years later.
Arguably the two greatest westerns ever, The Good, The Bad and The Ugly and Unforgiven, stand at complete opposite ends of the tonal and thematic spectrum for the genre. Eastwood’s crowning achievement as a movie star and Sergio Leone’s uncontested masterpiece is an unabashed, unhinged, downright operatic romanticisation of the western. On the flip side, Unforgiven, Eastwood’s crowning achievement as a director and his game-changing epilogue to an established career in the genre, strips away all romantic notions to construct a raw and brutal examination of how a life led by violence can only end in the same. A hollow and hellish existence, to be sure. Instead of the usual morally detached gunslinger his audience spent decades getting to know, Eastwood directs himself as a broken man who pretends to return to a life of killing because of simple monetary motivations, but is painfully aware of the curse that he inflicted upon himself: He’s not good for anything but getting drunk and killing men. David Webb People’s perfectly constructed screenplay flips the coin on Eastwood’s Man with No Name persona, and Eastwood as director returns the favor by creating an illuminating anti-violence treatise, replete with career-best performances from Morgan Freeman and Gene Hackman.