"Do I feel lucky?" The 25 Best Clint Eastwood Movies, Ranked

As a legendary figure in the American film industry, it's safe to say that Clint Eastwood has done just about everything when it comes to movies. He first rose to prominence by starring in a Western TV series in the late 1950s (Rawhide) and then playing The Man With No Name in The Dollars Trilogy in the mid-1960s. From the 1970s onwards, he also became well-known for directing and producing movies, and he's occasionally composed music for his own work, too.

Having a career that spans more than six decades makes it difficult to rank Eastwood's films, given the quantity and relative quality of them all. He's continued to work into his 90s, too, with the upcoming Juror #2 having been announced as his final project. In celebration of his vast filmography, what follows is a ranking of the greatest films he's starred in or directed (or both), starting with the good (no bad or ugly to be found here) and ending with the best.

25 'Play Misty for Me' (1971)

Play Misty for Me was a significant Eastwood film, seeing as it was his directorial debut. He would grow as a director over the coming decades, arguably peaking as late as the 1990s or even the 2000s, meaning Play Misty for Me certainly isn't one of his very best, but it's more than solid.

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It's a thriller about a disc jockey having an interaction with a particularly intense fan who becomes obsessed with him, with her behavior gradually escalating towards violence. It's worth watching for Arrested Development fans, as it has a very memorable performance by a young Jessica Walter as the fan/stalker in what's probably her most well-known movie role.

24 'Two Mules for Sister Sara' (1970)

After spending much of the 1960s playing Western characters, Clint Eastwood ended up keeping the Western streak going by making his first role of the 1970s a Western one. The film in question is Two Mules for Sister Sara, which pairs a mercenary with a nun in the Old West, following the surprisingly explosive adventure they end up going on together.

Eastwood stars with Shirley MacLaine, who plays the title character and is arguably the film's protagonist. It delivers classic Western thrills, and feels pretty lean and no-nonsense overall. Even if it's not one of Eastwood's most famous Westerns, it's still worth checking out for anyone who considers themselves a fan of his.

23 'Space Cowboys' (2000)

Despite the title, Space Cowboys is certainly not a Western. It's instead a rare movie about space travel that's not science-fiction, with it following four men who used to be involved with the Air Force - and early steps towards space travel - in the late 1950s who are brought back into the fold some 40 years later for a dangerous mission.

It was directed by Eastwood and features him playing the lead role, with a strong supporting cast including Tommy Lee Jones, Donald Sutherland, and James Garner. Its premise is a little out there and maybe kind of silly, but there's a certain amount of fun to be had with the movie, and at least the outlandish plot makes it stand out within Eastwood's filmography.

22 'Kelly's Heroes' (1970)

30 years before Space Cowboys, Clint Eastwood and Donald Sutherland starred in another movie together: Kelly's Heroes. It presents a surprisingly comedic story set during World War II, centering on a group of American soldiers who team up to go behind enemy lines to rob a bank.

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In being an irreverent war movie that emphasizes humor, it scratches a similar itch to the (admittedly more serious) M*A*S*H, also released in 1970 and also starring Donald Sutherland. Few of the comedies Eastwood's starred in are among his overall best movies, making Kelly's Heroes worth celebrating (and watching).

21 'The Beguiled' (1971)

Though the 2017 Sofia Coppola adaptation of The Beguiled is likely better known to modern viewers, this 1971 version shouldn't be overlooked. It takes place during the American Civil War, and centers on a soldier from the North (played by Eastwood) having to seek refuge at a Southern school, where seven women tend to him and also appear to fall for him.

Far from being a romantic film, though, it's more tense and dramatic in nature, with conflict arising when it becomes clear the women may not want him to leave, even after he's healed. It's a slow and quite strange movie, but it's unique and executes the potentially tricky premise relatively well for a film of its age.

20 'Where Eagles Dare' (1968)

Even by 1968 standards, Where Eagles Dare feels a little old-fashioned, but it is an impressively made and sometimes quite exciting World War II movie. It's about a daring rescue mission to retrieve an American general who's being held captive inside a heavily-guarded castle in Germany.

It stands out against Kelly's Heroes, as it's a more serious war movie without much by way of comedy, but also, as far as war movies go, it's more about action, heroism, and excitement than showing the horrors of combat. For those who don't mind WWII movies that aren't necessarily heavy on anti-war messages, Where Eagles Dare will very likely get the job done.

Six years before directing the infamous (and over-hated) Heaven's Gate, Michael Cimino directed Thunderbolt and Lightfoot, an engaging movie that pairs Eastwood and Jeff Bridges together. It's a somewhat comedic crime/action movie, feeling like a buddy comedy in a way, given Eastwood and Bridges make for a mismatched pair who need to work together to pull off an ambitious bank robbery.

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It's got the kind of grit, pacing, and moral ambiguity you can reliably expect from a crime/thriller that came out in the 1970s, and the two leads are surprisingly great together. It's an easy-to-watch and underrated Clint Eastwood movie, possibly overshadowed by many of the other great movies he was in around this time.

18 'Pale Rider' (1985)

1985's Pale Rider and 1973's High Plains Drifter merge together to some extent, as both make for dark and compelling Westerns with Eastwood playing a mysterious figure who's employed by a group of people in need, though under somewhat different circumstances in each.

Pale Rider centers on a preacher played by Eastwood, and what happens when he stands up for a village who are being targeted by a mining company that wants their land. It's effective at presenting what feels like a more realistic and downbeat depiction of the West than what you'd see in a more traditional Western, and it makes for a powerful and sometimes unsettling watch.

17 'In the Line of Fire' (1993)

In the Line of Fire features Eastwood playing a Secret Service agent who feels continued guilt about being unable to protect John F. Kennedy on the day of his assassination. He's shown to return to the job 30 years later, becoming tested when a potential assassin threatens the life of the current President.

It's a very Clint Eastwood role, and he slips into it well, almost to the point where he feels like he's on autopilot at some points. Beyond Eastwood's screen presence, In the Line of Fire additionally benefits from Wolfgang Petersen's typically skilled direction, and it also features a compelling villainous performance from John Malkovich.

16 'Richard Jewell' (2019)

The 2010s were far from the most consistent decade in Clint Eastwood's directing career, with some slightly underwhelming movies alongside a few good ones. Richard Jewell thankfully fits into the latter category, and its 2019 release ensured that Eastwood's 2010s did end on a relative high.

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It dramatizes a real-life story about the titular character - a security guard - thwarting a planned pipe bomb attack at the 1996 Summer Olympics, initially being hailed as a hero, though eventually becoming a suspect and having his life impacted severely through a trial by media situation. It's an engaging look at the way the news and poor police work can create a living nightmare for someone, with the film also benefiting from strong performances, most notably Paul Walter Hauser and Kathy Bates.

15 'The Outlaw Josey Wales' (1976)

The Outlaw Josey Wales is a violent and action-packed Western, having the kind of edge that made The Dollars Trilogy from the 1960s stand out. Clint Eastwood directed the film and played its titular character, a Western anti-hero who protects the downtrodden in a lawless West through (often) violent means.

It's one of Eastwood's toughest and most intense Westerns, and it's those qualities that help it stand out. Narratively, it might not sound particularly great or unique, but it's the style and the commitment to showing the brutality of the Old West which helps it shine and ultimately endure as one of Eastwood's best Westerns.

14 'A Perfect World' (1993)

There's a strong case to be made that A Perfect World is Clint Eastwood's most underrated directorial effort. In addition to directing, he also plays a supporting role in the film, with its story being about an escaped convict who finds himself in an unlikely friendship with a young boy while on the run from the law.

Eastwood plays the Marshal in charge of the pursuit, while Kevin Costner gives one of his best performances in the lead role, playing the convict. It's a surprisingly gentle movie, considering it's definable as a crime/thriller, and has a strong emotional core that serves to give the film's fairly standard narrative a welcome (and less expected) fresh coat of paint, so to speak.

13 'American Sniper' (2014)

American Sniper is easily Clint Eastwood's highest-grossing film, proving to be incredibly popular, especially in the U.S. It's also perhaps his best film of the 2010s, being a biographical war film about U.S. Navy SEAL Chris Kyle, who's known for being the deadliest marksman in U.S. military history​​​​.

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It's a tense and unnerving watch, and largely shines because of its central performance from a very committed Bradley Cooper. Its popularity meant it generated a great deal of discussion shortly after release, with some criticisms levied its way because of a perception that it's pro-war, though Eastwood himself has stated he intended for it to reflect anti-war sentiments.

12 'Flags of Our Fathers' (2006)

There's significantly less chance of people watching Flags of Our Fathers and interpreting it as pro-war, putting it in contrast with the slightly less clear American Sniper. It centers on several young American soldiers who fought in the Battle of Iwo Jima in World War II and were involved in the iconic photograph "Raising the Flag on Iwo Jima," which signified America's victory.

Beyond showing the conflict in confronting detail and with alarming realism, it also serves to show what happened to the young soldiers after they returned from fighting, and the difficulties that came with going back to civilian life. Flags of Our Fathersforms one half of a duology, with the other film - which shows the Battle of Iwo Jima from the Japanese perspective - being the better of the two (more on that later).

11 'The Bridges of Madison County' (1995)

The Bridges of Madison County is likely the most romance-heavy film Clint Eastwood has ever directed and/or starred in (he does both here). As such, it distinguishes itself pretty clearly from his more action-oriented films, given he makes films within the crime, war, Western, and thriller genres far more often.

Here, he stars with Meryl Streep in a movie about a married woman having a brief but intense affair with a photographer when he comes to the area to take photographs for National Geographic. It shows that Eastwood probably could've made a career out of making romance films if he'd wanted to, because The Bridges of Madison County proves to be a surprisingly moving and effective film.

10 'A Fistful of Dollars' (1964)

A definitive Spaghetti Western classic that made Eastwood a movie star and also established filmmaker Sergio Leone as one to keep an eye out for, A Fistful of Dollars is pretty great, to say the least. It also serves to kick off The Dollars Trilogy in style, following Eastwood's character attempting to take out two different gangs who are disturbing the peace in a small town by playing them off against each other.

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For as good as A Fistful of Dollars is, it's probably the "worst" of the three Eastwood and Leone collaborations. However, calling such a significant film the "worst" in any capacity feels wrong, so maybe it's just better to say that the movies that follow - in 1965 and 1966 respectively - are somehow even better.

9 'Escape from Alcatraz' (1979)

Escape from Alcatraz was one of the best movies from 1979, which is saying something, because it was a strong year for cinema overall. It's a heavily dramatized take on an infamous real-life escape attempt from the famed Alcatraz Prison in the San Francisco Bay, which occurred in the early 1960s.

It gets away with some historical inaccuracies, given it never feels like it's trying too hard to be based on a true story, and also, it's just super entertaining as is. It was one of the best movies Eastwood did with director Don Siegel; they made four films together between 1968 and 1971, with Escape from Alcatraz also being their last.

8 'Gran Torino' (2008)

Just as a certain Best Picture-winning movie from 1992 gave Eastwood a chance to say a bittersweet farewell to the kinds of characters he used to play in Westerns, Gran Torino feels partially designed to give a character like "Dirty" Harry Callahan a fitting send-off. There is a familiarity to the character Eastwood plays here, sure, but it's given a new spin owing to the fact that it's a film about getting older, falling behind on changing times, and finding redemption.

Eastwood plays a Korean War veteran who gradually befriends a neighboring Southeast Asian family and assists them when they come under threat from local gangs. It's bittersweet and very sentimental; some might also call it cheesy. But there is an earnestness to the film that makes it quite touching and powerful when it needs to be, ensuring it stands as one of the better Eastwood movies of the 21st century.

7 'Letters from Iwo Jima' (2006)

While Flags of Our Fathers was a compelling and sometimes devastating war movie, its companion film, Letters from Iwo Jima, is even more striking. It follows the Japanese forces on Iwo Jima as they become overwhelmed by the size of the U.S. Army, eventually coming to terms with the fact that a traditional victory may not be possible.

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There's something about the story here - and the way it's told - that makes it an extremely powerful war movie. By showing the conflict from a different side (and with Japanese dialogue), it serves to make Flags of Our Fathers and Letters from Iwo Jima a remarkable duology, highlighting the humanity, pain, and different kinds of losses felt on both sides of one terrible and tragic conflict.

6 'For a Few Dollars More' (1965)

Everything good about A Fistful of Dollars is made even better in the second Leone and Eastwood collaboration, 1965's For a Few Dollars More. Eastwood returns as The Man With No Name (he does get a new nickname here at least), and the film sees him team up with a bounty hunter after they both realize they're going after the same target (albeit for different reasons).

The story's more exciting, the scope is noticeably bigger, Ennio Morricone's score is even better than his score for the first film, and Eastwood plus Lee Van Cleef make for a great pairing. It somehow gets even better than this, as far as The Dollars Trilogy is concerned, but it does need to be stressed that this middle film is still fantastic.