5 Of Clint Eastwood’s Best Movies

Clint Eastwood2 5 Of Clint Eastwoods Best Movies

Although it’s now the commonly accepted opinion that the quality of Clint Eastwood’s movies isn’t what it once was, there was a period when he was possibly the best director in the business. It’s not just that his movies were excellent in so many ways and felt fresh in times where many regular moviegoers felt like they were watching the same kind of movie over and over again, but he’s been hugely influential in establishing an aesthetic for films perceived as serious. He grew into an absolute master of understated tone and completely stripped down aesthetic, fostering a kind of minimalism that served as a welcome contrast to the excess and bluster of the blockbuster moviemaking scene that only seemed to be growing in spectacle as time progressed.

Eastwood’s heyday is undoubtedly the mid-2000s, when he released a string of knockouts that floored audiences and awards panels alike. He’s had a long and storied career first as an actor and then as a director with flashes of greatness. He’s deservedly an icon and star, but also deserves credit for his visual prowess and storytelling ability. There are some directors who somehow seem to make every single scene of a movie engrossing, and he has does it in a way even more simply and delicately than most other American directors. He played strong and silent heroes, and his movies have been both of those things, making silence and quiet strength the most sought after virtues of prestige filmmaking.

There are 5 movies directed by Clint Eastwood that stand out as his best, and could be considered among the best of their years, decades, or more. Here they are listed chronologically rather than by ranking, because determining the best among these would be a fool’s errand.

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1) Unforgiven

Unforgiven 5 Of Clint Eastwoods Best Movies

A genre that is as old as the American movie industry itself, the Western is as much a staple of film as science fiction or fantasy, genres that get told on pages of literature but have a certain grandiosity that movies are uniquely equipped to provide. Unforgiven comes from a director well acquainted with the genre. Eastwood is best known for his portrayal of the Man with No Name in Sergio Leone’s spaghetti western movies culminating with The Good, the Bad and the Ugly. So he knew the territory well going into his own project, a pre-ordained farewell to the genre by one of its foremost veterans.

The result was a movie that took a surprising complex view of the Western. There’s something compelling about the elder statesman looking back on things, sharing pearls of wisdom about the progress or regression that’s been made. Often this consists of a lamentation that their relevance has passed. As the aged hero of Unforgiven, Eastwood calls into question the notion of heroism and justice in an environment where the right thing is not always so clear cut. It’s rightly referred to as an anti-Western, calling into question the very ideals upon which the traditional Westerns thrived. Its pacing and visuals also reflect this theme of aging, with the land itself appearing as old and tired as its hero, and its rhythm as careful and deliberate as a senior on stairs. This offers more pause, and more time for reflection on complicated matters like the ones presented in the film.

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2) Mystic River

Mystic River 5 Of Clint Eastwoods Best Movies

Eastwood’s next major critical success came 11 years after Unforgiven in an adaptation of a Dennis Lehane novel, Mystic River. Like his previous award-winning movie, this one is carefully paced, although there’s actually a surprising amount of stuff going on at once, quite a number of plates in spin at a time. It works as one part criminal procedural, one part psychological drama, and one part emotional tragedy. And you have three principal characters who inhabit each other those three dimensions at various points throughout the movie.

This is an example of Eastwood’s so-called minimalist style giving way for possible false perceptions that minimalism in final output equals minimal thought and effort. The mechanisms seem more apparent years later, with the performances of Sean Penn and Tim Robbins seeming somewhat less subtle than they came off 10 years ago at the time of the film’s original release, but they’re certainly no less powerful now than they were then. Also commendable about this film is the role of place, the setting of Boston. By now, with movies like The Departed and The Fighter, the idea that the city of Boston (and area) has its own character that comes to inhabit a film’s tone is commonplace. But Mystic River makes this a factor before it was chic, and perhaps in a more understated way. It’s all masterfully done and draws you in without even seeming like it’s trying, causing you to ask all sorts of moral questions that have no easy answers.

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3) Million Dollar Baby

Million Dollar Baby 5 Of Clint Eastwoods Best Movies

Continuing this trend of posing moral questions with no easy answers, Eastwood followed Mystic River up the following year with his second Oscar-winning feature, Million Dollar Baby. There are apparently a number of detractors of this movie now, but I would maintain that it deserves the accolades it received then just as much today.  Eastwood reteamed with old partner Morgan Freeman in this one, an even more visually and tonally pared down story of a boxing trainer and his female underdog boxing amateur.

This one may be most indicative of Eastwood’s style, love it or hate it. It’s epitomized by the style of music Eastwood makes, scoring this movie as well as others he has directed and others still that he did not direct. It’s very simple, quiet piano or guitar underscoring moments that are fittingly quiet and delicate. It follows the fighter genre to the extent that its characters wrestle with issues outside the ring as well as in, and the film treats this with the sort of gentle hand appropriate for a relationship between figures who become like father and daughter to one another. It’s beautiful, simple, and heartfelt, with a general quality maximizing the effects of its feelings and ideas. It seemed safe to assume this was as fine a film as Clint Eastwood could muster.

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4) Flags of Our Fathers/Letters from Iwo Jima

Flags of our Fathers 5 Of Clint Eastwoods Best Movies

Two years later, Clint Eastwood continued his streak of successes, offering up the most ambitious work of his entire career. Building on the interest shown in Unforgiven regarding heroism and truth, these companion pieces deal with this issue in a couple of really interesting ways. First, there’s the American perspective detailed in Flags, which seeks to unpack the real story behind the iconic image and propaganda tool of the American troops raising the US flag at the Battle for Iwo Jima in World War II. The men involved in the photo are fleshed out as complicated figures with conflicted views, and one scene in particular depicts the artificial nature of the photograph that was accepted as a candid account of what really happened.

Then there’s the Letters film, which takes this notion of truth that has been called into question by the previous film, and expands it even further, showing the battle as it’s perceived from the opposite end of the spectrum, the Japanese perspective. An even greater task than humanizing or complicating the American men hailed as heroes in the war, here Eastwood succeeds in humanizing those decried as the Enemy at the same time, providing an almost completely absent perspective on a barely understood conflict. It’s not often domestic audiences are put in the trenches with the individuals their country was fighting against, but Eastwood does precisely that in this movie, and to profound effect. It was ballsy. But it resulted in what may be the greatest work of his career.

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5) Changeling

Changeling 5 Of Clint Eastwoods Best Movies

Eastwood’s last truly great movie (not that any of his subsequent films have been terrible, save for perhaps Gran Torino), tells the true-ish story of the return of a woman’s disappeared son who turns out to be a different child altogether, and her refusal to accept the falsehood pushed on her by police results in a whole host of questions about power and the societal dismissal of women and corruption. Angelina Jolie controls the movie just as she did the previous year in A Mighty Heart, capturing the resiliency of this mother. It’s a pretty beautiful story of a feminist hero. While it was criticized for being generic and conventional, I found its emotional stakes to be entirely engaging and its themes more interesting than its somewhat straightforward plot would seem to indicate.

Changeling is likely another example of Eastwood’s ability to take a story and tell it in a way that seems simple but contains multitudes beneath the surface. It’s a hard thing to articulate, kind of like explaining how an actor can express a plethora of thought and feeling behind his or her eyes. It’s possible this was the last instance where I and many others were willing to give Eastwood the benefit of the doubt, before his simple style became perceived as simplistic. It’s also possible that his string of incredible movies raised the bar to an impossible height for him ever to reach again, and people express disappointment for that fact by feeling let down by his later movies.

Whatever it is, there’s no doubt that Clint Eastwood will end his career with one of the finest top five efforts among any filmmaker in movie history. For that, we should feel lucky.

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  • Guest

    #fail. Grand Tarino was terrible. On the contrary it was great.

  • http://www.facebook.com/people/Ben-Smith/100004127531754 Ben Smith

    Yeah, “Gran Torino” constitutes one of Eastwood’s best movies, and of course, “Flags of Our Fathers” and “Letters from Iwo Jima” represent two distinct films, even if they also serve as companion pieces. Personally, I think that “Letters from Iwo Jima” challenges “Unforgiven” for Eastwood’s best work.

    In recent years, I feel that Eastwood has continued to excel as a director. “Invictus” represented a step down from Eastwood’s previous six films (“Mystic River” through “Gran Torino”), all of which constituted masterpieces in my opinion, but it proved visually and emotionally elegant and perhaps amounted to the most inspiring movie that he has ever directed. “Hereafter” was graceful, somber, and endlessly fascinating, a film that brought Eastwood back to greatness, even if it proved too ‘European’ for critics and audiences. And “J. Edgar” represented a deconstructionist masterpiece in my opinion, a film that subverted and altered definitions of masculinity and treated a gay relationship with remarkable sensitivity and transcendence.

    Overall, though, I appreciate your article and I certainly concur with your conclusion!

    By the way, “A Perfect World” (1993) amounted to a major critical success for Eastwood, but it flopped at the domestic box office (although it found huge audiences overseas) and failed to receive the Oscar attention that it deserved. Along with “Bird” (1988), “A Perfect World” is one of Eastwood’s best.

  • http://www.facebook.com/people/Ben-Smith/100004127531754 Ben Smith

    By the way, I don’t see Eastwood’s directorial style as excessively simple or simplistic. He doesn’t employ gimmicks or flash, but perhaps no one’s films are more complex morally, while his visual coverage is far more diverse and sophisticated than that of most contemporary directors, who overload their compositions with closeups, tight coverage, and the same types of setups over and over. Eastwood’s directorial style is self-effacing in the sense that he doesn’t use dramatic camera movements and outlandish angles that call attention to the man behind the camera, but his style certainly isn’t one of painting-by-numbers.

    Additionally, “Flags of Our Fathers,” like “Bird,” does not possess a linear narrative, instead jumping back and forth in time and showing not just flashbacks, but flashbacks within flashbacks. “Hereafter” threads together three distinct narratives while emphasizing the passage of time rather than action in space (again, a European sensibility), and “J. Edgar” features an unreliable narrator who emerges as a professional and historical fraud, while the film also covers the topic of sexuality with ambiguity and restraint.

  • http://www.facebook.com/people/Ben-Smith/100004127531754 Ben Smith

    We do agree on “Letters from Iwo Jima,” certainly. As you said, it daringly filled a huge historical-cinematic void.

  • red stovall

    I understand your choice. But in my opinion, it’s a little bit hard to quote the five best Clint Eastwood movies: he has made a lot of good movies.

    For example, like many critics and moviegoers, you forgot some movies made before Unforgiven such as Play Misty For Me, High Plains Drifter, Breezy, The Outlaw Josey Wales, Bronco Billy, Honkytonk Man, Pale Rider, Bird and White Hunter, Black Heart. Of course, you could have quoted A Perfect World and The Bridges Of Madison County.

    Honestly, when I read your introduction and before reading your list, I expected all the movies you quoted but Changeling. Instead of Changeling, I expected Gran Torino. Many people think that Gran Torino is the best Clint Eastwood movie. At least, it’s their favorite one. Anyway, your list is solid and logical but maybe influenced by the critical acclaim of the movies you quoted.
    It’s always a pleasure to talk about Clint Eastwood movies. And I’m waiting for his next film which could be Jersey Boys. Bye !