Director Essentials: Clint Eastwood

by Patrick Bromley

A filmmaker who almost always Makes My Day.

Clint Eastwood is an icon and a legend, one of those movie stars who's recognized solely on a First Name Basis. While he originally made his mark in front of the camera in spaghetti westerns and thrillers like the Dirty Harry franchise, I would argue Clint did his best work as a director rather than as an actor. In fact, I'd argue that of all the actors to make the transition into filmmaking in the last 50 years, Eastwood might claim the top spot considering his range, his longevity, and his ability to tell lasting stories in a spare, clean style. Here are some of his essential movies.

1. Play Misty for Me (1971)

Clint's first film as director is a solid little thriller about a California disc jockey who gets Fatal Attraction'd (long before Fatal Attraction was a thing) by a fan played by Jessica Walter, 30 years away from her defining role as matriarch of the Bluth family. Like so many of the movies that followed, his first film is deeply personal and can be interpreted as either a misogynist text in which women be crazy or as a self-reflective study of a toxic man who treats women like shit and must reap what he sows. Either way, it's incredibly revealing about Clint as a person, his complicated relationship to women in his personal life, and his onscreen legacy as the pinnacle of alpha machismo. He's impossible to truly pin down throughout his seven-decade filmography. Play Misty needs to be on the list because it's the one that started it all: his career behind the camera, his thorny personal and gender politics being laid bare in his work, and even his incredibly quick and efficient shooting style -- the movie was brought in days under schedule and $50,000 under budget. This technical expertise learned from greats like Sergio Leone and Don Siegel, plus his total preparedness in the director's chair, served him well his entire career and enabled him to keep working into his 90s even when his movies weren't huge moneymakers.

2. High Plains Drifter (1973)

One might have predicted that Clint follow-up the success of Play Misty for Me by directing a western as his second feature, seeing as it's the genre that helped make him a huge star. What one might not have predicted is that he would have made one of the all-time great westerns, playing a stranger (of course) who rides into a mining town to seek revenge on the men who murdered a U.S. Marshal. What the movie doesn't quite come out and say but strongly suggests is that Clint is some kind of ghost or supernatural entity -- the personification of vengeance or the spirit of the murdered Marshal or something like that. The twist gives High Plains Drifter an identity that's totally different from other westerns of the period, and though Clint could play this kind of role in his sleep by this point, it's behind the camera where he really shines. His insistence on shooting on real locations (instead of the backlots the studio requested) and real sets grounds the movie in spite of some of the supernatural trappings and makes the world feel authentic even with its more mythic qualities. I know feelings about this one tend to be a little mixed, but I think Clint made an all-time banger western right out of the gate.

3. The Outlaw Josey Wales (1976)

Another great western with Eastwood behind the camera, though the story behind this one is a bit more controversial. Adapted from the 1972 book The Rebel Outlaw, Clint plays a farmer turned soldier during the Civil War who becomes a legendary gunfighter (and later outlaw, as the title suggests) after his family is murdered. Philip Kaufman, one of the movie's screenwriters, was originally slated to direct; he completed all of the pre-production and even began shooting but regularly clashed with star Eastwood. The two had radically different approaches; Kaufman wanted the film to be as accurate and detail-oriented as possible, while Eastwood had little patience for such a time-consuming approach and even disagreed with Kaufman's take on the title character. Eventually, Eastwood had Kaufman fired and took over the directing duties, which led to both a significant production fine and a new DGA rule called "The Eastwood Rule" that forbid such a thing from happening again. 

Sudden Impact (1983)

The only entry of the five Dirty Harry movies directed by Eastwood needs to be on this list because it's arguably his most iconic character (this or the Man With No Name) and the second best of the series. It's quite clear that the screenplay, a rape revenge story about a woman (Sondra Locke) who is assaulted and tracks down her rapists a decade later to kill them one by one, has been retrofitted into a Dirty Harry Callahan movie -- he's practically incidental to the story. That's not a knock against the movie, though, because Eastwood and Locke having parallel plot lines underscores the idea that the murderous vigilante and the trigger-happy cop are two sides of the same coin, mirror reflections of one another divided only by a Thin Blue Line. There's unpleasantness to be found for sure, but I love that between this and Tightrope (a Richard Tuggle film which Eastwood supposedly ghost directed, making it ineligible for this list), Eastwood was really leaning into early-'80s sleaze-core.

Unforgiven (1992)

If Clint has only one truly definitive masterpiece as a director, it's this one. While the rest of Eastwood's '80s and early '90s consisted of interesting work (Bird, Heartbreak Ridge) and perfectly good programmers (Pale Rider, The Rookie), it was in 1992 that he came roaring back to mainstream (and Oscar-winning) respectability with Unforgiven, the western to end all westerns. He plays a "reformed" bad guy who is hired to kill some men responsible for disfiguring a woman. Gene Hackman rightfully won a Best Supporting Actor Oscar for his portrayal of Little Bill, a bastard of a town sheriff who's not entirely in the wrong because that's the kind of movie Unforgiven is -- one that upends pretty much every single trope of the Western genre. Eastwood supposedly got the script in the early '80s but wisely held onto it for a decade; he needed to age into the role more and let the culture catch up to what he wanted to say. If we want to read too deeply into the film -- and really what are we doing here if not that -- a case could be made that it's about Clint doing penance for mistreating women both on screen and off for most of his career. I don't think that's what's actually going on in the movie, but Eastwood has consistently surprised me with his ability to be a thoughtful and even introspective filmmaker.

A Perfect World (1993)

Clint followed up the success of Unforgiven with what is still the most underrated movie in his entire filmography, 1993's crime drama A Perfect World. Kevin Costner plays a criminal who goes on the run and takes a young boy hostage with whom he begins to form a bond; Eastwood and Laura Dern are the cops trying to bring down Costner and bring the boy back home. This is a masterful crime drama featuring what might be the best performance Kevin Costner has ever given, and I love that Eastwood took on a supporting role to give Costner the space in the lead, subverting what was his movie star persona at the time to play such a terrible, tragic, complicated, and compelling character. This is a beautiful, haunting film still made within the Hollywood system and one of Eastwood's best.

The Bridges of Madison County (1995)

I'm not sure if this is one of Eastwood's most "important" movies, but it's worth including because it demonstrates his versatility as a filmmaker and his willingness to explore material outside of his usual westerns and thrillers, particularly as he got older. Clint Eastwood might be among the last actors you would expect to star in this adaptation of Robert James Waller's 1992 bestseller about the romance between a married Italian woman (Meryl Streep) and a photojournalist for National Geographic who comes to her Iowa town while her family is away and begins a passionate, if ill-fated, love affair. He's even less likely to be the one to direct, but that's exactly what he did after first Steven Spielberg and then Bruce Beresford dropped out. A huge box office success in 1995, Madison County also earned Streep another Best Actress Oscar nomination and made Clint a traditional romantic leading man for the first time in probably two decades. It's the sensitivity with which he directs the story, though, that makes it Essential Eastwood. It's another side of Clint.

Absolute Power (1997)

I'm picking this one not  because it's the best of Clint's paperback movies (a case could be made), but because it really kicked off his paperback run of the late '90s and early 2000s. After kind of a weird decade behind the camera, he settled into a very comfortable type of potboiler thriller beginning with this one adapted by the great William Goldman in which Clint plays a thief who witnesses the President of the United States (Gene Hackman) commit a murder during a late-night break-in. I love the paperback period (a term I've assigned to those Clint thrillers that demand very little of the audience and are mostly about forward momentum, same as a paperback you'd buy at the airport to read on the plane), but the movies that fall into this camp are rarely very substantive. Absolute Power at least carries with it some leftover '70s paranoia and mistrust of broken institutions, but is essentially a very entertaining and glorified star vehicle. With a cast that also includes Hackman, Laura Linney, Judy Davis, and Ed Harris, I'm not complaining.

Mystic River (2003)

After a few years spent in the paperback thriller wilderness (which produced movies like True Crime and Blood Work), Eastwood returned to critical respectability with this Oscar-winning adaptation of Dennis Lehane's novel of the same name. There's a ton of great stuff in Mystic River, a kind of Shakespearean drama about the murder of a young girl ripples through several families and the police in Boston, but I would argue that the two performances that won Academy Awards (Sean Penn for Best Actor and Tim Robbins for Best Supporting) are the weakest elements in an otherwise Very Good Movie. Clint captures a very specific sense of place and never underplays the tragedy of what, in other hands, might have been a more standard revenge thriller. His original score does a ton of the heavy lifting and is among the best he ever contributed to a movie. This kicked off a second (or third) Golden Age of Clint as a filmmaker, during which he did what might be the best work of his career behind the camera.

Letters from Iwo Jima (2006)

I don't think I can make a list of Clint Eastwood's essential films that doesn't include this one, a companion piece to his Flags of Our Fathers, which was released the same year and details the WWII Battle of Iwo Jima from the perspective of the American soldiers. It's a good movie but a flawed one. Considerably better is Letters, which looks at the same event from the Japanese point of view and is as haunting and elegiac a war movie as has been made in the last 40 years. I still remember a critic (I can't recall who) referring to Eastwood at the time Letters from Iwo Jiwa was released as the "American Kurosawa" and that always stuck with me: a prolific filmmaker working inside a studio system who consistently produced thoughtful films dealing with issues of regret and redemption in a clean, spare style. Hopefully the critic wasn't using that comparison just because Eastwood had made a Japanese film.

It's rare for an American filmmaker -- particularly one as iconic and identifiably "American" as Eastwood -- to tell a story from the perspective of another country and another culture; it's even rarer for that filmmaker to do it in that country's native language, as Eastwood does here. There is so much depth and ambition to the undertaking of both of these movies that just the fact Eastwood was willing to take it on forced me to rethink him as a director at the time; here was a guy known for wanting to work quickly and cheaply tackling this massive project, two movies about the same event told from differing perspectives, one entirely in Japanese. Both are good, one is basically a masterpiece.

American Sniper (2015)

I'll admit that I was not crazy about this movie when it was released in late 2015, but I'm self-aware enough to recognize that part of my resistance to it has to do with the culture wars that sprang up around the film and propelled it to be the biggest and most successful movie of the year and the highest-grossing movie Eastwood ever directed. I was also distracted by the fucking rubber baby, which seemed to me a symbol of Clint's general disinterest in doing the work of directing -- his desire to make movies under budget and under schedule finally culminated in what I perceived as laziness and sloppiness. I know now that Clint hadn't completely lost interest in filmmaking (he made a couple of really good movies after this one, plus a couple of not-so-good movies...looking at you, The 15:17 to Paris) and I can probably dismiss a shortcut like the rubber baby as an unwillingness to worry to much about some of the smaller details. We could argue as to whether or not the baby is a "smaller detail," of course, but you get what I'm saying. I also know that, removed from said culture wars and my own biases,  this is a better movie than I gave it credit for being -- an attempt to look at PTSD and what is often considered "moral" violence honestly from a filmmaker who built a career largely on violence.

Juror No. 2 (2024)

What may very well end up being 94-year old Clint Eastwood's final work is another of his paperback movies, but it's a real page-turner and one of the best movies of its year. Nicholas Hoult does career-best (to this point) work as a man who winds up serving on the jury of a crime he may or may not have committed himself. If Clint is going to retire after this one, it's a good one on which to go out: not only is it the sort of compelling, well-acted dramatic thriller he's been making for over 50 years, but it also speaks to many of his regular themes and obsessions -- how the wrong people can be railroaded and the broken American systems that allow for injustices to take place. I know that Clint and I don't always agree politically (if you don't believe me, I've got an empty chair I'd like to sell you), but the politics of his films are often more difficult and nuanced than contemporary discourse allows. He has always been impossible to fully pin down, making his work infinitely more interesting and timeless than that of his sometimes reactionary counterparts. He has a deeply complicated legacy, but there's little arguing he's one of the best to ever do it in Hollywood.