All 40 Movies Directed by Clint Eastwood, Ranked

Sometimes known as The Man with No Name, Clint Eastwood is also the Director Who Won’t Slow Down, even into his 90s. His career is fascinating, and plainly extends beyond just directing, of course. He rose to prominence back in the late 1950s, thanks to the TV show Rawhide, and then became a film star by the time the 1960s came around. Indeed, that decade saw the release of what’s probably the best film he starred in without directing: The Good, the Bad and the Ugly.

Starting in the early 1970s, Clint Eastwood also began directing, sometimes starring in the movies he directed while also appearing in movies he didn’t direct (like Escape from Alcatraz and In the Line of Fire). To focus on his directorial credits, though, what stands out first of all is how consistently Eastwood’s worked as a director. Between 1971 and 2024, he made 40 feature films, which would be staggering if he just focused on directing… but as mentioned before, he’s also acted a whole bunch during this time, too. While not every film of his is a masterpiece, he’s certainly been behind some great ones, and surprisingly few total duds, too. What follows is a ranking of every film Eastwood has directed, starting with the not-so-great and ending with some genuine classics.

‘The 15:17 to Paris’ (2018)

Starring: Ray Corasani, Spencer Stone, Anthony Sadler

There was an attempt at something bold with The 15:17 to Paris, but the execution let it down. It dramatized a real-life story about three American men who thwarted a terrorist attack on board a train while vacationing in Europe. The boldness came from the fact that it got the three actual men to essentially play themselves, recreating the central event while also acting out moments from their lives leading up to it.

It’s a noble idea, but the three leads don’t appear particularly comfortable – or even natural – playing themselves. You can appreciate what they did, but it’s harder to be wowed by their performances here, as harsh as that might be to say. Elsewhere, The 15:17 to Paris is quite sloppily put together from a writing and editing perspective, and what should’ve been a stirring thriller instead becomes a very clunky melodrama.

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‘The Rookie’ (1990)

Starring: Clint Eastwood, Charlie Sheen, Raúl Juliá

As will become clear in a bit, Clint Eastwood had a pretty good decade in the 1990s, all things considered, especially because it saw him find considerable awards success (wins for Best Picture and Best Director the same year). But things didn’t kick off amazingly well in this decade, seeing as 1990 saw the release of The Rookie, a movie that feels as though it was directed by one.

It might sound enticing on paper, because the idea of a cop movie starring Eastwood and Charlie Sheen is, in concept, possibly too weird to be boring, but no… The Rookie is boring. It feels so much longer than the two hours it runs for, and seeing flat action sequences and continual scenes of Sheen and Eastwood clashing really gets old surprisingly fast.

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‘Firefox’ (1982)

Starring: Clint Eastwood, Freddie Jones, David Huffman

Describing Firefox will make it sound more interesting than it is, perhaps even more so than was the case with The Rookie. This is a Cold War movie that flirts with the sci-fi genre while (purportedly) being an action/thriller film, following Eastwood’s character, a skilled pilot, going to the USSR to steal a top-secret jet fighter that the Soviets are developing.

You’ve got paranoia, a clear objective, and Eastwood doing his usual stoic thing… it should all make for a fun movie, but outside a few brief moments of life here and there, Firefox is a rather plodding flick to actually watch. There’s a common sentiment that mediocre movies should be remade more than already good movies, and that could be said about Firefox, perhaps, if the Cold War was still going. It’s sadly relegated to being a relic of its time, and a pretty underwhelming/disappointing one at that.

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‘Hereafter’ (2010)

Starring: Matt Damon, Cécile de France, Bryce Dallas Howard

Firefox was unusual for being an (almost) science fiction movie directed by Eastwood, whose films tend to be grounded more in reality, and Hereafter is similarly novel for being kind of a fantasy movie; emphasis, maybe, on “kind of.” It’s mostly a drama, and it also plays out like a disaster movie, especially in its first act, thanks to one rather spectacular sequence early on that depicts the 2004 Indian Ocean tsunami.

The film follows a woman who miraculously survives said event, and the way she’s potentially mysteriously connected to two other people who have some kind of link to the afterlife. There are big ideas that are prodded at in Hereafter, but it never dives as deep into such things as it could or should. It comes close to being moving at times, but it’s the kind of film that just doesn’t stick the landing, and it ultimately becomes regrettably tedious to watch, at a certain point.

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‘J. Edgar’ (2011)

Starring: Leonardo DiCaprio, Naomi Watts, Armie Hammer

J. Edgar feels a little torn between being something subversive and unexpected, and something a little more by-the-numbers, as far as biopics go. Unsurprisingly, the central figure here is J. Edgar Hoover, and the film does what it can to capture a sizable chunk of his life, with Leonardo DiCaprio playing Hoover over numerous decades, complete with some pretty unconvincing old-age make-up.

It’s a movie that’s at its most interesting when exploring sexual repression, given that’s the kind of surprising part of what otherwise seems like a standard biopic about a noteworthy American individual from the 20th century. The engaging/striking stuff gets a little lost in the overall film, though, which can sometimes be overwrought and a bit dull. There are both things to admire and dislike in J. Edgar, in starkly equal measure, really.

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‘Blood Work’ (2002)

Starring: Clint Eastwood, Jeff Daniels, Anjelica Huston

Not quite a legendary thriller by any means, but a more or less competent one, Blood Work contains one of Eastwood’s final lead performances; indeed, he only had prominent roles in five movies since 2002. He’s been more focused on directing as he’s gotten older, it seems, and that’s resulted in some great movies. Not Blood Work, though. Not really. This one’s just okay.

It’s expected stuff as far as cop movies go, with Eastwood playing an FBI profiler who comes out of retirement to work on a case that involves tracking down a serial killer. It’s not very successful as a mystery movie, but provides some fun bursts of action here and there, and seeing an older Eastwood be gruff and sarcastic is always, at the very least, a little bit entertaining.

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‘The Gauntlet’ (1977)

Starring: Clint Eastwood, Sondra Locke, Pat Hingle

Long stretches of The Gauntlet are unfortunately a bit dull, but the movie comes alive at certain points at least, mainly when it focuses on delivering action. It’s got the sort of simple premise that fits well with that genre, being about a cop who’s tasked with escorting a high-profile witness out of Las Vegas, contending with the various people who want her dead.

It’s one of several movies Eastwood starred in with Sondra Locke, but not one of the pair’s better ones. The Gauntlet does admittedly avoid overstaying its welcome too much, clocking in, mercifully, at under two hours, and it’s generally put together in a competent enough way. Things drag at certain points, though, and the overall film can feel surprisingly lifeless at times, even with the high stakes that seem inherent to its central story.

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‘Bronco Billy’ (1980)

Starring: Clint Eastwood, Sondra Locke, Geoffrey Lewis

It might sound like sacrilege, but Eastwood’s work as a director was far more inconsistent in the 1970s and 1980s than it was in the 1990s and 2000s, the latter two decades being when the filmmaker was generally at his best. Hell, you could even argue that the 2010s saw the release of generally better Eastwood films compared to his first two decades spent behind the camera. That sense of Eastwood bettering his craft can be appreciated if you’re willing to do a deep dive into his filmography.

But you will come across films like Bronco Billy, which just don’t really stand out or excel. To Bronco Billy and the credit of similar films, though, at least they don’t stand out in bad ways, either. This is just a very standard and perhaps overly loose-feeling romantic dramedy with a bit of a modern Western vibe. It comes and then it goes, all in just under two hours, and that’s that.

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‘Heartbreak Ridge’ (1986)

Starring: Clint Eastwood, Marsha Mason, Everett McGill

Clint Eastwood has directed a handful of great war movies in his time, though Heartbreak Ridge isn’t quite one of them. It’s tonally odd, not to mention a bit plodding, like many other less-than-great or generally mediocre Eastwood-directed flicks. The focus here is more on training than combat, which isn’t the problem; after all, consider how captivating something like Full Metal Jacket is while exploring that area of military life.

The problem is more than Heartbreak Ridge isn’t hugely engaging on an emotional front, nor particularly insightful in what it has to say about war. One could praise it for being neutral or seeming well-balanced, sure, but there’s still the problem of it not being entirely engaging. That might sound overly negative for a film that’s still admittedly competent, but Heartbreak Ridge just falls a bit short, and it’s kind of a disappointment, rather than a true hidden gem within Eastwood’s sizable filmography.

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‘The Eiger Sanction’ (1975)

Starring: Clint Eastwood, George Kennedy, Vonetta McGee

Once again, the word “competence” rears its not quite ugly head. Its underwhelming head? Disappointing head? That came out wrong. Um, yeah, The Eiger Sanction is sort of competent for an action/adventure movie. Nothing more, nothing less. The story is about an assassin out for revenge, and there is also a lot of snow, meaning it’s one of Eastwood’s chilliest movies.

Nothing more of any real note can be said here. The Eiger Sanction exists. Eastwood broods, comes out of retirement, and gets tangled up in some fairly ho-hum action set pieces. It might be easier to recommend if it was a little more brisk, but the film feels regrettably flabby thanks to its runtime, which exceeds two hours. Big Eastwood fans might find some enjoyable elements here, but otherwise, it’s hard to get too enthusiastic about this one.

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‘Honkytonk Man’ (1982)

Starring: Clint Eastwood, Kyle Eastwood, John McIntire

There are fans of Honkytonk Man, and some might consider it one of Clint Eastwood’s more personal and underrated movies, so that should be acknowledged. It’s almost a musical, too, being focused on a young boy and his uncle as they travel around during the Great Depression, the latter being a musician who’s struggling more than ever due to a nationwide lack of money.

Clint Eastwood stars alongside his son here, Kyle Eastwood, and Honkytonk Man is also one of several films directed by the former that showcases his passion for music. It is a very languidly-paced film, and that lack of tightness can make it drag at times, but it captures the era in which it’s set fairly well, and one gets the sense Eastwood certainly wasn’t on autopilot here. It just would’ve been great if the passion here was a little more infectious.

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‘Absolute Power’ (1997)

Starring: Clint Eastwood, Gene Hackman, Ed Harris

It’s easy to mix up Absolute Power with various other action/crime/drama movies from the 1990s, which was a decade when people seemed willing to name such films as generically as possible. Or, maybe the star power was what counted here, over any kind of catchy title, because there are some big names in Absolute Power, including Gene Hackman, Ed Harris, Laura Linney, and Judy Davis (alongside Eastwood himself, of course).

The plot here is about a thief witnessing a murder that involves the President of the United States, and then going on the run after being in the wrong place at the wrong time puts his life in danger. It’s a paranoia-heavy film that should be a bit more gripping than it is, but it’s nonetheless solid and only a little disappointing. With appropriately tempered expectations (hard to do when that cast is so good, admittedly), it’s a pretty decent watch.

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‘Sully’ (2016)

Starring: Tom Hanks, Aaron Eckhart, Laura Linney

Not to be mixed up with a certain Robert Zemeckis movie about the aftermath of a risky airplane maneuver that saved lives, Sully is differentiated from that one (Flight) because it’s directly based on a true story. It stars Tom Hanks as a pilot who landed a malfunctioning plane on the Hudson River, which ended up saving the lives of the 150+ people on board.

Sully kind of peaks with the inciting incident, and the bulk of the movie (you know, the aftermath) fails to be quite as dramatically interesting. But it does succeed in a retelling of a still fairly recent actual event, all the while being solidly acted and assembled from a filmmaking perspective. Insert joke about Eastwood being on autopilot here (but autopilot Eastwood, it has to be said, can still crank out a decent film).

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‘The Mule’ (2018)

Starring: Clint Eastwood, Bradley Cooper, Laurence Fishburne

There’s more simplicity to be found in the very straightforward The Mule, which is, as of writing, the penultimate Clint Eastwood film he both starred in and directed. It’s a movie that sees him going back to the ever-familiar crime genre, with the story here focusing on an elderly man who, due to desperate financial stress, ends up becoming a drug courier.

Owing to Eastwood’s age, and the age of his character, The Mule is, by design, hardly a thrilling kind of crime film, but it’s an empathetic and sometimes emotionally successful one. It depicts a kind of hardship faced by those who are aging in a blunt and generally honest way, and in its lighter moments, The Mule can also be surprisingly life-affirming and even a little funny.

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‘Changeling’ (2008)

Starring: Angelina Jolie, John Malkovich, Jeffrey Donovan

Changeling is a pretty grueling watch; if not Eastwood’s absolute bleakest, then it might be a contender. The premise here involves a woman’s child going missing for several months, and then further complications ensuing when she’s “reconnected” with him, but is firmly of the belief that the kid is – to paraphrase the King of Pop – not her son.

It’s another one of these Eastwood-directed films that’s pretty good, albeit not exactly great. Angelina Jolie is very good here in the lead role at least, and there are other solid performances to be found here (Clint Eastwood movies that aren’t The 15:17 to Paris can be relied on to generally contain good acting). You might not be wowed overall, then, by Changeling, but it’s still pretty satisfying as a drama with a period setting.

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‘True Crime’ (1999)

Starring: Clint Eastwood, Isaiah Washington, LisaGay Hamilton

Sorry, but Blood Work, Absolute Power, and True Crime do kind of blur together, so forgive any commentary for the last of those sounding a touch familiar. These three Eastwood movies all have crime/drama/thriller elements, came out around the same time, and share a similar feel… not to mention the fact that all are, unfortunately, a little sluggish from a pacing perspective.

Thankfully, the acting here’s dependably good, and True Crime has something of a pulse at times thanks to a story about a journalist who believes a man on Death Row is actually innocent. It could’ve benefited from being a little more breathless and/or exciting, but True Crime – once more – gets the job done. And, to its credit, it’s perhaps a touch more compelling than either Blood Work or Absolute Power.

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‘Jersey Boys’ (2014)

Starring: John Lloyd Young, Vincent Piazza, Michael Lomenda

Clint Eastwood’s passion for music emerges once more in Jersey Boys, which is kind of the closest he’s come to directing a Martin Scorsese crime movie. You could even argue that Scorsese would’ve done this material a little better (there’s profanity, some mob elements, a narrative spanning years, voiceover, and Joe Pesci… not as an actor, but as a character!), but there’s still something fun about seeing Eastwood tackle it.

Jersey Boys is mostly about Frankie Valli and the forming of the Four Seasons, exploring the ups and downs that came with forming the group and touching upon how they were somewhat connected to the mob. It’s an uneven film for sure, and not always an enthralling one, but it comes alive at certain points and ends up being a solid – and sometimes distinctive – take on the music biopic genre.

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‘Space Cowboys’ (2000)

Starring: Clint Eastwood, Tommy Lee Jones, Donald Sutherland

It doesn’t matter if the title sounds stupid and the movie itself might be flawed; one does not simply turn down a movie that stars Clint Eastwood, Donald Sutherland, and Tommy Lee Jones, among others. There are lots of cool old people in here being cool old dudes, and that makes Space Cowboys a quintessential “dad film,” for those who are either older men or simply have that dad frame of mind.

And, sure, dad movies don’t always get critical acclaim or feel particularly clever, but sometimes, their blunt charm is just what the doctor ordered. Space Cowboys follows a bunch of old guys going on a generally entertaining trip into space, reliving their youths while engaged in a rather high-stakes mission. It’s kind of a hangout movie, it’s kind of dumb, but it’s also sort of hard to resist, and might well qualify as underrated, all things considered.

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‘Sudden Impact’ (1983)

Starring: Clint Eastwood, Sondra Locke, Pat Hingle

It’s hopefully not controversial to say that the Dirty Harry series commenced with what was easily its best film, and eventually ended with its worst (the fifth). Near to the end (but not a nadir) was Sudden Impact, the fourth featuring Harry Callahan, and the only Dirty Harry movie to be directed by Clint Eastwood himself. Interestingly, each of the five movies had a different director, too.

Anyway, with Sudden Impact, the narrative involves Callahan having to deal with a female vigilante who’s out getting very justifiable, and violent, revenge on numerous terrible people. There are questions raised by the film surrounding what she does versus what Callahan does, and though it’s never as in-depth as would be ideal, Sudden Impact is admirable for giving viewers something to chew on at least, alongside being another fairly entertaining Dirty Harry sequel, on more of a gut/basic level.

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‘Invictus’ (2009)

Starring: Morgan Freeman, Matt Damon, Tony Kgoroge

A historical film that doesn’t take place all that long ago in the overall scheme of things, while also functioning as something of a sports movie, Invictus is about rugby being used as a way to try and bring people together in South Africa right after the apartheid era. It is exactly what you’d expect it to be, but there’s nothing too wrong with that when beats are sufficiently hit and appropriate emotions are mined.

Like too many Clint Eastwood films to mention, Invictus is a little longer than it needs to be, but there’s more here that works than doesn’t work. It’s also better than the other Eastwood-directed movie starring Matt Damon (Hereafter), but it’s not as good as the other films Eastwood directed Morgan Freeman in (more on those Best Picture winners in a bit).

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‘Cry Macho’ (2021)

Starring: Clint Eastwood, Eduardo Minett, Natalia Traven

This placement might raise some eyebrows, but those sentimental about Clint Eastwood and his legacy will likely find parts of Cry Macho to be genuinely moving (while other parts are, sure, a bit clunky). This is, as of 2025, the final movie Eastwood has starred in, and will probably be his last, given the man’s now in his mid-90s and Cry Macho feels so effectively like a swansong, too.

It’s one of the actor/director’s lesser Westerns, sure, but it almost shouldn’t be compared to them. It’s a gentler, slower, and – appropriately – older-feeling Western than anything else Eastwood’s made within the genre, but it feels like a fitting cinematic equivalent of a victory lap for someone whose career took off thanks to the Western genre; as mentioned before, on both the TV screen in the late 1950s and during the 1960s on the big screen.

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‘Flags of Our Fathers’ (2006)

Starring: Ryan Phillippe, Jesse Bradford, Adam Beach

The lesser part of a war duology, though still quite good in its own right, Flags of Our Fathers is partly about the Battle of Iwo Jima, seen from the U.S. perspective, and partly about its aftermath. On both fronts, there’s a particular focus on a famed photograph showing six men raising an American flag on Mt. Suribachi, uncovering the truth behind it and how those captured in the image dealt with life after the battle was over.

Effectively anti-war in its approach to one of many battles fought during World War II, Flags of Our Fathers is somber, gritty, and sometimes quite moving. It was released the same year as Eastwood’s superior companion film about the Battle of Iwo Jima (to be elaborated on a little down the line), but both halves of this overall story – well, two halves of the same story, arguably – are nonetheless worth experiencing.

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‘Midnight in the Garden of Good and Evil’ (1997)

Starring: John Cusack, Kevin Spacey, Jude Law

With a fairly long title and a relatively long runtime of 155 minutes, Midnight in the Garden of Good and Evil feels wider in scope than many other Clint Eastwood movies dealing with crime and justice. Eastwood’s returned to exploring such themes time and again, doing so in ways that were inferior to this film, but at the same time, Midnight in the Garden of Good and Evil is exceeded in quality by various other thematically similar Eastwood movies.

Still, there’s a certain eeriness to this one that’s easier to admire, with its plot concerning a reporter looking into a high-stakes murder trial that involves one very wealthy individual. Midnight in the Garden of Good and Evil doesn’t need to be more than 2.5 hours long, but most of it is pretty good, and it ends up feeling as though it’s one of Eastwood’s more underappreciated efforts overall, even with a few flaws holding it back from true greatness.

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‘Play Misty for Me’ (1971)

Starring: Clint Eastwood, Jessica Walter, Donna Mills

It’s understandable why Jessica Walter is best known for Arrested Development, but as far as film performances go, Play Misty for Me is probably her most famous/memorable. Essentially, she plays an obsessive fan of a disc jockey (played by Eastwood), with the film being a slow-burn thriller about her obsession growing increasingly dangerous and, eventually, violent.

Play Misty for Me is also noteworthy for being the first feature film Clint Eastwood directed, and came out the same year he starred in the first Dirty Harry film. So it’s a little overshadowed by that one, but it works as a pretty good – and unabashedly direct – thriller, and it is of undeniably strong quality for a directorial debut. Following this one, Eastwood did indeed move on to both greener and, uh, browner(?) pastures.

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‘High Plains Drifter’ (1973)

Starring: Clint Eastwood, Verna Bloom, Marianna Hill

Funnily enough, here’s Clint Eastwood’s second feature film as director, High Plains Drifter, which was a minor improvement upon his debut, Play Misty for Me. As a film, it’s kind of a big deal, because after starring in a fair few iconic Westerns, Eastwood tried his hand for the first time at directing one here, and he did a far from bad job.

Also starring in the film, High Plains Drifter sees Eastwood as a gunfighter who stumbles into a town, proves his alarming skill with a gun, and then gets hired by the townspeople there to kill a few more men. It’s a slow and atmospheric Western that gets pretty dark and unsettling at times in a way that feels novel, mitigating the fact that the pacing does make it feel a little uneventful at times, at least on a narrative front. But for evoking the unique mood it does, this one’s worth seeking out.

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‘Richard Jewell’ (2019)

Starring: Paul Walter Hauser, Jon Hamm, Kathy Bates

The 2010s wasn’t as fruitful a decade as the 2000s were, regarding Clint Eastwood and the films he directed, but Richard Jewell did sneak into the former decade, and worked as a more than solid drama inspired by real events. That puts it in line with Sully, having another story about someone’s act of heroism leading to intense scrutiny, but it handles such a premise – and the relevant themes – in a more compelling fashion.

It’s competently written and edited, though ultimately elevated by its performances, with Paul Walter Hauser (in the titular role) and Kathy Bates being especially great. It’s another Eastwood film that kind of starts, plays out, and then ends the way you’d expect it to, but hey, it’s efficient, well-acted, and covers an interesting real-life story, so that all makes Richard Jewell feel like more than enough.

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‘Bird’ (1988)

Starring: Forest Whitaker, Diane Venora, Michael Zelniker

Okay, this is the last time a Clint Eastwood movie will be described as too long, but it is the biggest thing that holds Bird back from being a top-tier work by the director. It’s an engaging biopic about Charlie ‘Bird’ Parker that sprawls out across 161 minutes, in a way that some might find dull, while others might see it as the cinematic equivalent of improvising in a fittingly jazzy way.

It wanders around and rambles, but that could be part of the point; it feels intentional, so viewing it that way makes the length arguably a little more understandable. And Bird is striking as a portrait of a skilled and iconic – yet also troubled – artist, with its approach, style, and length working to set it apart from most other music-focused biopics out there.

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‘Breezy’ (1973)

Starring: William Holden, Kay Lenz, Roger C. Carmel

Released the same year as High Plains Drifter, Breezy is easily one of the most overlooked Clint Eastwood films, and one of his most distinctive. It’s a fairly straightforward romantic drama, and though not the only film of the director’s that could be described as such, it’s still not the kind of movie Eastwood’s typically associated with, as either an actor or director.

With Breezy, it was the first movie he directed that he didn’t also star in (though he has an uncredited cameo, Alfred Hitchcock-style). Instead, William Holden and Kay Lenz star in this, playing two very different people – of very different ages, too – who form a strange kind of connection after crossing paths by chance. That age gap is indeed what Breezy explores, and it does so tastefully for something of its age, but it would be understandable if some modern-day viewers turned on the movie because of the premise flat-out.

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‘Juror #2’ (2024)

Starring: Nicholas Hoult, Toni Collette, Chris Messina

Call it recency bias if you want, but Juror #2 is genuinely a very good courtroom drama that was remarkably released the year Clint Eastwood turned 94, and even if the film hadn’t been good, that achievement in itself would still be impressive. If it’s to be his directorial swansong, then it really wouldn’t be a terrible one to go out on, because Juror #2 is a very Eastwood-esque exploration of justice and morality.

Juror #2 concerns a man who’s sitting on the jury for a murder trial, and finds himself torn between saving himself and doing what he’s supposed to when he realizes he may have inadvertently played a role in the crime itself. It’s a well-paced and admirably lean movie, packed with strong performances and, though not flashy, it’s easy to watch and surprisingly entertaining.

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‘The Bridges of Madison County’ (1995)

Starring: Meryl Streep, Clint Eastwood, Annie Corley

Alongside Breezy, The Bridges of Madison County is another rare romantic drama directed by Clint Eastwood, though he stars in this one, unlike that other 1973 film. But then again, the best performance in this one’s ultimately given by Meryl Streep, playing a housewife who strikes up a brief but passionate romance with Eastwood’s character, a photographer.

There’s a certain sadness that hangs over much of The Bridges of Madison County, by design, making it bittersweet; not entirely lacking in sentimentality or tenderness, in other words. It’s a film that seeks to capture how love can be tumultuous and defined by heavy ups and downs, even when it’s between two people who met when they were (more than) almost young. It’s mature, patient, and successful in showing a different side to Eastwood as a director.

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‘American Sniper’ (2014)

Starring: Bradley Cooper, Sienna Miller, Kyle Gallner

The best Clint Eastwood film made since 2010 is American Sniper, which serves as both an interesting war movie and an undoubtedly strong biopic. It’s about U.S. Navy SEAL Chris Kyle, taking something of a Flags of Our Fathers-like approach by exploring scenes of combat alongside the experience of returning home after fighting and struggling to readjust to civilian life.

It was also a bit divisive, at least among some circles, but American Sniper does feel like it’s trying to make you think about whether war and the notion of heroism can exist side by side. Some might feel it celebrates what it shouldn’t, some might feel it’s appropriately critical or at least neutral, while some might feel it celebrates something it should. American Sniper doesn’t really judge, but it does ask questions. Few people feel neutral about it, and that’s impressive for a film directed by someone who, during production, was well into their 80s.

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‘White Hunter, Black Heart’ (1990)

Starring: Clint Eastwood, Jeff Fahey, Charlotte Cornwell

Is White Hunter, Black Heart the most underrated Clint Eastwood movie? Maybe! It’s the kind that you’re unlikely to really learn about unless you do a deep dive into his filmography, or try to watch everything he starred in and/or directed. It’s a genuinely fascinating and unfairly overlooked film, following an American director who splits his time in Africa between filming and hunting, increasingly pursuing the latter over the former, causing inevitable drama.

Eastwood gives an incredibly committed performance here as a truly flawed man, and directs the entire film with a similar amount of skill. White Hunter, Black Heart has continually interesting insights into violence, creativity, and obsession, taking a simple premise and doing complex things with it thematically. It also makes great use of its setting, being among Eastwood’s best-looking movies in the process.

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‘Pale Rider’ (1985)

Starring: Clint Eastwood, Michael Moriarty, Carrie Snodgress

Sure, the premise of Pale Rider is similar to High Plains Drifter, but the approach and overall feel differ, making both Clint Eastwood Westerns inevitably worth seeking out. Eastwood’s a mysterious stranger once again (shock, horror) who’s gruff and skilled with a gun, and finds himself hired by some desperate townspeople to protect them against the aggressive forces of a nearby mining company.

He’s not quite the Man with No Name here, but Eastwood does play a man who says he’s a preacher, and he is only credited as “Preacher,” so perhaps you can link Pale Rider thematically to those older Sergio Leone Westerns starring Eastwood. It’s a visually striking watch and another worthy exploration of familiar themes, characters, and iconography. Eastwood just does this kind of Western so well that it’s kind of hard to resist, even with the sense of déjà vu.

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‘A Perfect World’ (1993)

Starring: Kevin Costner, Clint Eastwood, Laura Dern

A Perfect World isn’t a perfect movie, but it’s also not far off. It came out one year on from Clint Eastwood’s first (of two) Best Picture wins, and while not quite hitting the same highs, proved to be far from a disappointing follow-up. It takes a strange premise and makes it work shockingly well, following the odd friendship that forms between a convict on the run and a young boy he kind of kidnaps.

There would’ve been many ways for A Perfect World to go wrong, but it generally sidesteps such potential issues and emerges as a really strong crime-flavored road movie. Eastwood’s good in a supporting role, and Kevin Costner turns in one of his very best performances in the lead role here, as the oddly likable escaped prisoner. It’s a little underrated, perhaps, and a lot of good.

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‘The Outlaw Josey Wales’ (1976)

Starring: Clint Eastwood, Chief Dan George, Sondra Locke

If it weren’t for one other movie released in 1992, The Outlaw Josey Wales would ultimately stand as the best Western Clint Eastwood ever directed. It’s still probably his most shocking and confronting, exploring violence in a way that felt unflinching, even back in the rather uncompromising decade for filmmaking that was the 1970s.

It’s unsurprisingly a movie that sheds light on the outlaw side of life, back in the Old West, but does so in a way that makes its titular character (played by Eastwood) an antihero; someone initially hellbent on revenge, but then has a greater purpose thrust upon him. There’s an energy and anger felt in The Outlaw Josey Wales that ensures it still packs a punch, and a strong argument to be made that it was the first truly great film Eastwood directed.

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‘Gran Torino’ (2008)

Starring: Clint Eastwood, Christopher Carley, Bee Vang

As previous films have likely shown by now, Clint Eastwood isn’t opposed to having his films get a little sentimental, though it might well be Gran Torino that’s his biggest tearjerker… in a good way, it should be stressed. This is one of four great movies Eastwood directed between 2003 and 2008, all being responsible for the 2000s standing as the director’s single best decade (and, again, all these were made while Eastwood was in his 70s).

Of these four movies, Gran Torino has the biggest part for Eastwood to play in front of the camera, portraying a Korean War veteran who learns to overcome prejudice and ultimately finds redemption for the things he believed and did in the past. There is very little about Gran Torino that’s subtle, when it comes to exploring things like racism and generational gaps, but it gets away with it because it’s an intensely sincere movie. It is blunt, and sometimes messy, but it means well, and proves supremely stirring when it needs to be.

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‘Mystic River’ (2003)

Starring: Sean Penn, Tim Robbins, Kevin Bacon

Gran Torino was bittersweet, in many ways, but Mystic River was mostly just bitter, standing as a truly harrowing crime/drama film about grief and the lingering consequences it can have at its most intense. Three men are all impacted in different ways when one of them suffers an unthinkably awful tragedy, leading to the unraveling of certain – and continually distressing – truths.

That’s all to say that Mystic River is not a fun or entertaining movie in the traditional sense, but it’s extremely engrossing, even if you might find that one watch is enough (it’s a tough one to try and revisit, once you know what’s coming). It’s a movie that digs deep and hits hard, showcasing Eastwood at his best as a director while also having some great acting, with Sean Penn and Tim Robbins, in particular, both turning in career-best performances.

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‘Million Dollar Baby’ (2004)

Starring: Hilary Swank, Clint Eastwood, Morgan Freeman

The darkness keeps coming and it don’t stop coming, because one year after Mystic River, Clint Eastwood directed another devastating movie: Million Dollar Baby. This feels like a deconstruction of a typical sports movie; the kind that’s not afraid to say: “You might want something really badly, but that doesn’t, by any means, ensure you’ll get what you’re after.”

That’s life, but that’s not usually what sports movies go for, so that means Million Dollar Baby really stings. It’s remarkable, though; again, not a fun movie, but one that’s engrossing for just about every minute of its runtime. It understandably became the second movie directed by Eastwood to win Best Picture, and he gives a great performance here, too, as do Hilary Swank and Morgan Freeman.

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‘Letters from Iwo Jima’ (2006)

Starring: Ken Watanabe, Kazunari Ninomiya, Tsuyoshi Ihara

The second part of a duology, with the first part being the aforementioned Flags of Our Fathers, Letters from Iwo Jima is the even stronger half. It’s an unbelievably powerful anti-war film, exploring the Battle of Iwo Jima once more, but this time centering on the Japanese perspective. Hopelessness and death hang heavy throughout. Sympathetic and very human characters are introduced, fleshed out, and then killed without warning. On it goes. It never stops being upsetting.

It works to make Flags of Our Fathers hit harder, too, when one assesses the whole picture and sees what a horrible battle this was for all involved. But when judged individually, Letters from Iwo Jima is the one that hits harder. It is an incredibly sensitive movie, hitting all the emotional notes it needs to without relying on melodrama or forced sentimentalism. It’s still too early to say for sure, but decades from now, it might well emerge as Eastwood’s most timeless film; the one that could well endure the longest.

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‘Unforgiven’ (1992)

Starring: Clint Eastwood, Gene Hackman, Morgan Freeman

Yet for as good as those 2000s releases are, Clint Eastwood’s single greatest achievement as a director was a movie he made a little earlier: Unforgiven. Well, “earlier” comparatively speaking. Unforgiven is still a film that feels late-era, in the sense that it feels like an older, wiser, more mature, and more brutally honest Western than anything Eastwood had been involved with before. Legacy and the past are explored, both narratively and thematically.

In front of the camera, it’s probably Gene Hackman who shines the brightest, but Eastwood’s performance here could debatably be his greatest, Morgan Freeman is fantastic, and Richard Harris – though not in the movie much – does temporarily steal the movie. Behind the camera, Clint Eastwood’s never done better work, though. Unforgiven is tense, exciting, emotional, surprising, tragic, uncompromising, and startlingly entertaining/approachable. It just does everything right, never really hitting a false note. On top of being the best-directed Clint Eastwood movie, Unforgiven is also just flat-out one of the greatest Westerns ever made, too. Some Best Picture wins are divisive, but this one was more than well-deserved.

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