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Top 10 Clint Eastwood-Directed Films

by Warren Cantrell on September 13, 2011

in Top 10s

Clint Eastwood is cooler than you.  Clint Eastwood is cooler than your dad, grandfather, uncle, brother, and the most tremendous dude you know, combined.  When speaking to the man, if one were so honored and blessed, it would be advisable to keep eyes closed and head turned lest your face melt away in some awesome reaction to Eastwood’s blinding masculinity a-la Raiders of the Lost Ark.  Put simply, this guy is the bee’s nuts.  Throughout a television and film career spanning roughly sixty years (60!), this man’s unwavering integrity and commitment to cinematic excellence has set him apart, both as an actor and a director.

In this regard, fans of the 10rant know what time it is, for Mr. Eastwood’s work appears so frequently in my website’s rankings that the man now has his own tag.  This isn’t the first time I’ve devoted a list specifically to one man’s achievements.  The Top 10 Gary Busey, Christopher Walken, and Bill Paxton Performances lists all took the time to rank an outstanding gentleman’s work in cinema, thus it can be seen as nothing less than an insult that it took so long to get Mr. Eastwood his own list.  For this, only I am to blame.  Reparations have arrived in the form of today’s ranking, however!

I’ve made a gentleman’s pact with Mr. Mean Melin about a top 10 double pack, wherein he tackles Mr. Eastwood’s most outstanding acting examples, whilst I devote my time to the directorial efforts. Oaths were taken and pacts made, leading to the first entry in this honorable Eastwood tribute.  The deciding factors for the entries in the directorial top ten below were weighed via the assessment of criteria including personal satisfaction (15%, -ish), cultural relevance (30% -ish), cinematic ingenuity (30% -ish), and social importance (25%).

Throughout his career, Clint Eastwood has demonstrated an astonishing ability to make movies that are fun, interesting, innovative, and socially responsible.  This is a feat few have pulled off, especially over so long a period.  Some very, very near misses included Absolute Power (which I liked!), and A Perfect World, which damn-near snuck onto this bad boy, yet finally lost out to…

10. Changeling (2008)

Of all the movies listed today, Changeling scores highest on the “let’s never do that again” scale.  A magnificent movie, it was also excruciating at times, and carried with it a brooding sense of dread that seemed to seep into the very fabric of the characters’ clothes. The film told the true story of a single mother in the 1920s that lost her child to an abductor. The mother’s plight and the seeming impotence of the L.A.P.D. pressured the police to come up with a favorable response, which they provided in the form of a young boy claiming to be the missing child.  Angelina Jolie played Christine Collins, the distraught mother who was initially relieved at her son’s return…until she realized it wasn’t her son. The cops, in an effort to smooth over the situation and put a nice spin on the events for the press, found a kid who looked similar to Christine’s boy, tried to pass the child off as the genuine article, then had Christine committed when she started making a little too much noise about the whole affair.

Mr. Eastwood’s thoughtful touch behind the camera was evident in each scene (especially any with the villainous, though never overstated Chief Davis, played by Colm Feore).  The true anchor of the film was clearly Jolie, however, who turned in a performance as passionate as it was painful.  The understated, patient attitude which eventually developed into a manic hysteria spoke volumes about the historical period in which it was set, and was a testament to a director who has always brought thoughtful consideration to his period pieces.  Speaking of which…

9. Bird (1988)

Clearly a labor of love from a director who has never made any secret of his appreciation of jazz, Bird is probably the most personal of Mr. Eastwood’s directorial efforts. Brimming with sly references, jokes, nicknames, and quirks only to be understood by the most seasoned jazz aficionado, the film was still accessible to a broad audience due to its grounding in essential human traits such as loyalty, despair, and lust.

Charlie “Bird” Parker (Forest Whitaker) was an exceptional musician with a wealth of opportunities and support who still could not claw his way out of the prison built out of his own petty addictions.  Eastwood’s sympathetic tone never gave way to any thematic compromises, for the overwhelming thrust of this picture was undoubtedly an effort to celebrate the majesty of pure genius whilst lamenting the familiar consequences that so often accompany it. Hardly a thematic standout in Mr. Eastwood’s directorial catalogue, this biopic picture told a similar story frequently seen in the man’s work.  It told the tale of a man who lived in a world no longer fit for him; it spoke about a character running out of time, and making poor decisions with the what little remained.  Like this next film, it presented a main character that might normally seem unattractive, yet became something akin to a familiar uncle for the audience by the end…

8. Gran Torino (2008)

If you want to talk about impressive, let’s break off a little respect for Mr. Eastwood’s successful management of a film that required its audience to accept a seventy-eight year old action hero. And that’s only half of it! You know who played that same seventy-eight year old?  Fuck yeah! Eastwood, son! Though Eric will no doubt expand on this notion more when he writes the Top 10 Eastwood Acting Performances, I thought it worth a moment to reflect on ol’ Clint’s ability to not only make a gripping film, but also rip to shreds a role in one of those same pictures. In Gran Torino he played Walt Kowalski, the most grizzled and raw man on the planet.

Through an almost comedic series of events, Walt became friendly with a Hmong family that lived next door, and as is often the case in Mr. Eastwood’s work, the movie followed its main character (Walt) through his evolution from a cynical, broadly racist asshole to a caring, sympathetic human being. The progression of Mr. Eastwood’s character was neither predictable nor straightforward, and it did not provide any easy answers for the characters in the film, all of whom had to deal with painful realities born out of an unfamiliar relationship without much precedence. Said to be Mr. Eastwood’s last acting role, this should be remembered as one of the director’s finest works, both as an actor and a filmmaker.

7. Play Misty for Me (1971)

The cinematic harbinger for the scorned female lover formula that Fatal Attraction revolutionized roughly fifteen years later, Play Misty for Me was well ahead of its time in more ways than one. Mr. Eastwood’s first directorial offering, Play Misty for Me was about a popular California D.J. that stumbled into what he believed to be a harmless fling, only to realize the chick he’d bagged was six different shades of crazy. It started harmless enough.  Eastwood’s Dave hooked up with a random fan at a bar, thought the tryst done with, then began noticing that the woman (Jessica Walter’s Evelyn) wasn’t the kind of broad to be shaken.

No, Evelyn didn’t take hints too terribly well, and she began showing up at Dave’s house, important business meetings (which she had a tendency to ruin) and even at the house of Dave’s girlfriend (oops!). Naturally, a crazy-broad story wouldn’t be complete if the scorned chick didn’t try to kill herself, which is exactly what Evelyn tried to do, in Dave’s house, no less! Of course this all boiled down to a riveting finale where the audience thought Evelyn was gone, only to have the rat-shit crazy maniac show up at the last minute for one final spook of the audience. A very tight, exciting, well-conceived and perfectly executed picture, it would normally be hard to believe that this was a director’s first effort. Well, hard to believe if it was anybody but Eastwood.

6. Mystic River (2003)

Few directors have the ability to pull performances out of their actors better than Mr. Eastwood, an attribute that is among the most impressive yet least discussed amongst the man’s talents. Tim Robbins walked away with the Best Supporting Actor Oscar while Sean Penn scored the big boy for their performances in Mystic River, making this neither the first nor the last time one of Mr. Eastwood’s films has led to an Academy Award for one of his actors. Every detail of the picture spoke to the complete investment of the director, a man who clearly thought through the color scheme of each character’s wardrobe, each scene’s lighting, each moment’s impact.

It told the story of an angry and distraught father (Penn’s Jimmy), a man who gave in to the worst aspects of human nature to quell feelings no less terrible. A fairly straightforward story that followed a tragedy of errors born out of mistakes and bad decisions, Mystic River was an honest examination of the nature of man in a desperate state, and the capacity for evil as a response to evil. An exquisite film from the bottom up and back again, everything from the crisp yet subdued cinematography to the thoughtful performances to the courageous ambition of a director bold enough to tell a difficult story made this one of the best films of the last decade.

5. Pale Rider (1985)

This one is often overlooked when there’s a discussion about Mr. Eastwood’s directorial prowess. A somewhat unique movie in the man’s catalogue, Pale Rider was an abnormally religious film that dealt with fairly heavy Judeo-Christian themes. Eastwood’s “Preacher” protagonist was nothing less than the cinematic embodiment of Christ in the form of a gun-slinging badass with no name.  His character had been oppressed and murdered by the state only to find a rebirth whereby the fallen martyr was resurrected and took His kingdom back from the infidels. In short, Pale Rider was the American West’s biblical manifestation of the second coming. And if some movie is going to throw around a pseudo-Christ figure who also happens to be the nastiest man who ever slapped iron, well, it better fucking be Clint Eastwood!

The man is just a few rungs below some sort of half-deity, anyway, much like Hercules, so why not? In Pale Rider, Eastwood’s character not only saved the day for the pious, well-meaning settlers, but he did so at the end of a revolver, punishing the wicked with disciples by the name of Colt, Smith, and Wesson. An awesome movie that is also considerate of the historical period and the religious themes so skillfully interlaced into the plot, this was actually the first Clint Eastwood film I ever saw, and it remains one of my favorites.

4. Million Dollar Baby (2004)

There was a lot of squabbling that went on a few years ago when this picture came out, for it confronted a serious hot-button topic (assisted suicide) in a very skillful, efficient, thoughtful manner.  Because this was the case, it was hard for people to ignore this film, no matter how much they may have disagreed with the ending, or their perception of Million Dollar Baby’s message. Critics like Michael Medved, pundits like Rush Limbaugh, and other right-wing werewolves that feast upon the blood of the innocent came out in full force against this picture, going so far as to explicitly give away the ending because they disliked it so much.

And to think: all this because of a wily seventy-something jazz lover felt like making a character study centered on the relationship between a boxer and her trainer. In Million Dollar Baby, Eastwood directed himself with the same casual confidence that has seen him in good stead professionally as an actor these last sixty or so years. His Frankie Dunn was a very precise, layered, thoughtful individual who nonetheless had a very defined arch. One of the strengths of this picture was Eastwood’s ability as both a director and an actor to present characters that followed very realistic, sometimes painfully predictable paths. This picture didn’t offer any easy answers, not for its characters (the scenes with Maggie’s family were especially diabolical) nor for its audience. A courageous and audacious film that deserved every single accolade, Million Dollar Baby stands as one of Mr. Eastwood’s finest achievements.

3. The Outlaw Josey Wales (1976)

Produced at a time when the Western genre was considered a cold commodity not worth the trouble or cost of development, The Outlaw Josey Wales was a risky venture from pretty much every angle.  Though not a rookie, Eastwood was hardly a proven director in 1976, so his movie, where Confederate guerillas and Native Americans were the protagonists, couldn’t have looked all that attractive to the studios. Set in the period immediately following the American Civil War, the picture asked its audience to sympathize with figures who had traditionally played the roles of villains in Western cinema. Yet The Outlaw Josey Wales wasn’t just about challenging established Hollywood conventions, it was an allegory for the epoch in which it was released. Fresh out of Vietnam and mired in the social, racial, and cultural backwash created by a country that had drawn battle lines on the home-front, this picture had a lot to say about how one could go about healing in a post-war environment.

Reeling from a shattered presidency, crippled economy, embarrassed foreign policy agenda, and failed social revolution, the United States in 1976 was a fragmented, largely drugged-out mess. The Outlaw Josey Wales was set in a similar period and a familiar place. The picture told a different American story, one that was set during another social crossroads, when people hitherto known only as Americans emerged from a war with new concepts of “us” v. “them” for their fellow citizens.

Mr. Eastwood’s 1976 western told the story of a man, Josey Wales, who started the film as a jaded Confederate who harbored only thoughts of hatred and revenge for his northern countrymen. As the movie progressed, Josey learned that he had it in him to change, and to accept those he’d once known only as his enemies. He took to riding with two Native Americans, one an old man and the other a young woman, as well as with a group of Union settlers with ties to Josey’s former Yankee enemies. The film was about healing divisions within a country and amongst a common people; it maintained that there’s room in a hard heart for understanding and change. A thoughtful picture that confronted traditional Hollywood archetypes as well as pressing social issues that were extremely relevant at the time of its release, The Outlaw Josey Wales still stands as one of the finest pictures of the 1970s, and one of Mr. Eastwood’s finest contributions to the cinematic field.

2. Flags of Our Fathers & Letters from Iwo Jima (2006)

These could have only come from Mr. Eastwood, a man who has defined his directing career through a series of courageous and unconventional choices with his projects. Just as Josey Wales challenged its audience to re-think conventional assumptions about the American West, Flags and Iwo Jima dick-slapped a twenty-first century American film community that thought it had transcended a century’s worth of racial boorishness. Movies that were released just a couple of years before Eastwood’s double feature, films like Pearl Harbor and Windtalkers, largely adhered to the conventional Hollywood practice of presenting the Japanese antagonists one-dimensionally and without any humanity.

While Anglo enemies of this period are sometimes afforded some character or sympathetic attributes (see A Midnight Clear or even Kelly’s Heroes), Japanese characters that have appeared in World War II films have rarely been offered anything more than a murderous snarl and a pair of wild eyes. Intent on telling a story about the Battle of Iwo Jima, Mr. Eastwood did what probably seemed to him to be the only option: he told two stories.

Representing the American half, Flags of Our Fathers dealt with the age-old dilemma of crowning “heroes” during wartime, and how the benefits of this convention may serve to inspire the majority while offering nothing but guilt to the object of that praise. In war, the needs of the many often outweigh the needs of the few, so it would seem only appropriate that a soldier be expected to bear this burden, though most would tell you that they would prefer death to such endless torture.

In the Japanese piece, Letters from Iwo Jima, Mr. Eastwood shifted his focus to the defense of the island, and what it means to be a hero in the more quiet sense of the word. Ken Watanabe’s Gen. Kuribayashi knew that the fight was a hopeless one in terms of conventional victory or defeat, yet fought on nonetheless, well aware that every second that the American forces spent taking his misshapen hunk of sand and rock was another that his people were safe.

For the American victors, the story was less about the fight and more about what it did to the men who survived it.  Devoid of anything more than a handful of survivors, the Japanese knew no such luxury, and had to fashion their heroes in another manner. Though the U.S. had a victory (and a great photograph) to frame their narrative, the Japanese had only the silenced voices of soldiers too heroic to tell their own story. Though he approached it from different directions, both thematically and literally, Mr. Eastwood’s message between the two pictures was static. In war, the true heroes are the ones that don’t come back. For the Japanese, this was a far more manageable notion to appreciate since so many of their fighting sons never returned. For the Americans, the victors, this came with a lot more difficulty, and more casualties outside those generated from the battlefield.

1. Unforgiven (1992)

One of the films in my personal top 10, Unforgiven was successful because it was able to weave a fictional narrative into a historical setting, and to do so in a way that did perfect justice to both the time period and the artistic medium involved. At the heart of Unforgiven was an unflinching examination of humanity’s proclivity to act terribly in the name of justice, and what it meant to live in a world where people could enforce their own personal version of righteousness with the pull of a trigger.

Little Bill’s (Gene Hackman) sense of right and wrong differed, but was no better, than the men who he beat, jailed, or otherwise punished. The cowboy who had cut up the prostitute thought he was doing right by providing compensation for the damages. The prostitute co-workers of the victim thought they were doing right by contracting for the cowboys’ deaths. Ned and William Munny (Eastwood) thought themselves justified in killing the cowboys as punishment for their transgressions. Humanity is filled with stories of people acting terribly in an attempt to do right; what made the American West so exceptional during the 19th century was that there was so much opportunity and leeway to act on these individual moral concepts. Many did indeed act, and acted violently, and a legacy was thus born for a nation still derided to this day as a bunch of “cowboys.”

A liberating breath of fresh air for a fictional genre that had roots in cheap mid-19th century literature, Unforgiven corrected a slew of historical inconsistencies that have evolved into accepted truths over the course of roughly 150 years. The dime novels of the 19th century told Western stories that readers largely devoured en masse, regardless of the outright fabrications and liberal stretching of truths as it concerned the setting, characters, and social dynamics of the events involved. Character archetypes were codified during this period, and rigidly defined the proper place of all non-white men in the fictional Western setting. This trend of painting women as victims, the Native Americans and Mexicans as villains, and all minority classes as questionable-to-devious carried over into the cinematic age, where film and television studios churned out uncomplicated stories that followed the existing blueprint.

As audiences got more savvy throughout the 1960s and 70s, there was no longer a demand for simple characters going through the predictable motions, and it took a total re-imagining of the genre vis a vis Sergio Leone to salvage the genre.  Out of that fiery cauldron of artistic revolution came an actor most had not yet seen, at least for any length of time. Clint Eastwood used the acting celebrity that grew out of Leone’s westerns to move into directing, a job he utilized to bring a bit more balance and understanding to a genre he had helped to resurrect.

The Outlaw Josey Wales began this trend, yet it wasn’t until Unforgiven that Eastwood perfectly articulated his defiant renouncement of the traditional western mythology.  In Unforgiven, the film gave its audience characters that were neither good nor bad, but instead represented a social and moral ambiguity that was in perfect harmony with the historical realities of the period. Everybody in the movie thought they were doing right, yet at the heart of their reciprocity, at the crux of their scale-balancing, was murder.  Only in a time and place as wild and undefined as the American West could something like this have been possible, for what made the West so interesting (both at the time of its existence and today) was the ability of a person to make their own rules in a land that embraced the improvised laws of new landlords. While this was not always the reality for the actual people who ventured west of the Mississippi River after the Civil War and before the dawn of the twentieth century, it was true enough in enough cases that a literary (and later, cinematic) genre grew out of the tall tales and myths from this period. 

Unforgiven was but one attempt (albeit the most successful) by a director to correct this misconception, to bring a house Mr. Eastwood helped re-build back in order, and on a responsible foundation.

“Obvious Child” is the debut novel of Warren Cantrell, a film and music critic based out of Seattle, Washington. Mr. Cantrell has covered the Sundance and Seattle International Film Festivals, and provides regular dispatches for Scene-Stealers and The Playlist. Warren holds a B.A. and M.A. in History, and his hobbies include bourbon drinking, novel writing, and full-contact kickboxing.


{ 2 comments… read them below or add one }

1 Shawn September 13, 2011 at 7:30 pm

As a huge fan of Eastwood I agree with this list whole heartedly. I’ll throw in one more movie, not one I would add to Eastwood’s top 10 but one that deserves to be seen. If you can get passed the 80s cheese, Heartbreak Ridge is Eastwood as the actor and the director in one of the few modern war films that took place between Vietnam and the Gulf.


2 Trey Hock September 13, 2011 at 9:40 pm

Whenever you think Clint Eastwood is too cool, it’s always good to remember Firefox.


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