"Do I feel lucky?" The 30 Best Clint Eastwood Movies, Ranked (2024)

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 No. 2 having been announced as his final project.

There are a ton of Clint Eastwood movies out there, both the ones he's directed and starred in (and of course, sometimes, he does both). The prolific nature of the man who is Clint Eastwood means diving into his filmography can be daunting, but there are some of the best Clint Eastwood movies out there, all serving as good entry points. 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.

30 'Cry Macho' (2021)

Appeared as Mike Milo

Cry Macho is likely going to be the final Western Clint Eastwood will ever make. No one's going to call it one of his greatest, but it's still surprisingly good and certainly bittersweet, with Eastwood directing and starring in this movie about an ex-rodeo star helping an old boss by traveling to Mexico to find said boss's missing son.

It's a fairly low-stakes and perhaps even relaxing film, which feels fitting, given its star and director was in his early 90s when it got made. It's a solid swansong to the genre that made Eastwood a star back in the 1960s film-wise, or as far back as the 1950s TV-wise, and is worth a watch for any fans of his who may have missed it.

Cry Macho

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Release Date

September 17, 2021

Director

Clint Eastwood

Cast

Natalia Traven , Eduardo Minett , Dwight Yoakam , Clint Eastwood , Horacio Garcia-Rojas , Fernanda Urrejola

Runtime

104 minutes

Main Genre

Drama

29 'Every Which Way but Loose' (1978)

Appeared as Philo Beddoe

It's silly enough that perhaps some would call it more of a so-bad-it's-good movie rather than a genuinely good one, but either way, there is a certain stupid appeal to Every Which Way but Loose. It's a largely plot-free movie, and follows a man and his orangutan as they go through life causing chaos and getting into various fights.

It was nevertheless a hugely successful movie as far as the box office was concerned, and has a certain novelty for being perhaps the goofiest movie Eastwood ever starred in. He's best known for being a tough guy on-screen in generally serious movies, so there's a charm in watching him play a goofier sort of role in a very silly movie like this one.

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28 'Sully' (2016)

Directed by Clint Eastwood

Not quite a classic biopic/historical drama film, but still a pretty good one, Sully tells the dramatic real-life story of Captain ‘Sully’ Sullenberger, a pilot played by Tom Hanks. The film details how he saved the lives of 155 passengers on board his plane by making a risky landing onto the Hudson River, and then follows the aftermath ofg the incident, including how Sullenberger was investigated in a manner that threatened his public image and career.

It probably peaks early, thanks to the entire crash sequence being its most thrilling aspect, but everything that follows is still reasonably compelling to watch. Grounded by a typically strong Hanks performance, decent direction from Eastwood, and a brief runtime of just 96 minutes, Sully largely works.

Sully

PG-13

Biography

Drama

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Release Date

September 9, 2016

Director

Clint Eastwood

Cast

Tom Hanks , Aaron Eckhart , Laura Linney , Valerie Mahaffey , Delphi Harrington , Mike O'Malley , Jamey Sheridan , Anna Gunn

Runtime

96 Minutes

27 'Blood Work' (2002)

Appeared as Terry McCaleb

Standing as one of Clint Eastwood's more underrated movies, Blood Work shows the director in solid late-career form, given he was in his 70s by the time he made this one. It follows an FBI profiler coming out of retirement to investigate a case surrounding a serial killer, as he believes his own blood analysis may provide a clue to this person's identity.

It takes itself seriously, but there are a few offbeat moments throughout that give it some additional personality, and the supporting cast, which includes Jeff Daniels and Anjelica Huston, is also strong. It doesn't set the crime/thriller genre on fire by any means, but Blood Work still works, and makes for a good watch.

Blood Work

R

Drama

Action

See Also

Every Clint Eastwood Movie, Ranked And In Release Order35 Clint Eastwood movies, ranked from worst to best - Time OutClint Eastwood movies: 20 greatest films ranked worst to best

Crime

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Release Date

August 9, 2002

Director

Clint Eastwood

Cast

Clint Eastwood , Jeff Daniels , Anjelica Huston , Wanda De Jesus

Runtime

110 minutes

26 'Magnum Force' (1973)

Appeared as Inspector "Dirty" Harry Callahan

The Dirty Harry series could often be relied on to provide solid action movie fare, and besides the original, the best in the series would have to be the second movie, Magnum Force. It's about Police Inspector Harry Callahan investigating a group of shady police officers, and making certain startling discoveries that continually place him in further danger.

It's the kind of movie where viewers will know what they're getting in for, and those expecting a gritty and fast-paced - if sometimes simplistic - Eastwood action movie will have a blast. The sequels released after this one represented something of a dip in quality, but fans of Eastwood will likely get a kick out of the first two Dirty Harry movies at least.

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25 'Play Misty for Me' (1971)

Appeared as Dave Garver

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.

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.

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24 'Two Mules for Sister Sara' (1970)

Appeared as Hogan

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 Western's female 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.

Two Mules for Sister Sara

PG

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Release Date

May 28, 1970

Director

Don Siegel

Cast

Clint Eastwood , Shirley MacLaine , Manolo Fábregas , Alberto Morin

Runtime

114 Minutes

Main Genre

Western

23 'Space Cowboys' (2000)

Appeared as Colonel Francis D. "Frank" Corvin, Ph.D., USAF (Ret.)

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.

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22 'Kelly's Heroes' (1970)

Appeared as Kelly

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.

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).

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21 'The Beguiled' (1971)

Appeared as Corporal John 'McBee' McBurney

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.

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20 'Where Eagles Dare' (1968)

Appeared as Lt. Morris Schaffer

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.

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Appeared as "Thunderbolt"

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.

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.

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18 'Pale Rider' (1985)

Appeared as The Preacher

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.

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17 'In the Line of Fire' (1993)

Appeared as Secret Service Agent Frank Horrigan

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.

In the Line of Fire

R

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Release Date

July 8, 1993

Director

Wolfgang Petersen

Cast

Clint Eastwood , John Malkovich , Rene Russo , Dylan McDermott , Gary Cole , Fred Dalton Thompson

Runtime

128

Main Genre

Action

16 'Richard Jewell' (2019)

Directed by Clint Eastwood

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.

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.

Richard Jewell

R

Drama

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Release Date

December 13, 2019

Director

Clint Eastwood

Cast

Nina Arianda , David Shae , Ian Gomez , Mitchell Hoog , Sam Rockwell , Randy Havens , Paul Walter Hauser , Olivia Wilde , Kathy Bates , Jon Hamm

Runtime

129

15 'The Outlaw Josey Wales' (1976)

Appeared as Josey Wales

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 that helps it shine and ultimately endure as one of Eastwood's best Westerns.

The Outlaw Josey Wales

PG

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Release Date

June 30, 1976

Director

Clint Eastwood

Cast

Clint Eastwood , Chief Dan George , Sondra Locke , Bill McKinney , John Vernon , Paula Trueman

Runtime

135 minutes

Main Genre

Western

14 'A Perfect World' (1993)

Appeared as Chief "Red" Garnett

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.

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13 'American Sniper' (2014)

Directed by Clint Eastwood

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​​​​.

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.

American Sniper

R

Biography

Drama

Action

War

Where to Watch

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Release Date

December 25, 2014

Director

Clint Eastwood

Cast

Bradley Cooper , Sienna Miller , E.R. Ruiz , Luke Grimes , Jake McDorman , Max Charles

Runtime

132minutes

12 'Flags of Our Fathers' (2006)

Directed by Clint Eastwood

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 Fathers forms 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).

Flags of Our Fathers

R

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Release Date

October 18, 2006

Director

Clint Eastwood

Cast

Ryan Phillippe , Jesse Bradford , Adam Beach , John Benjamin Hickey , John Slattery , Barry Pepper

Runtime

132

Main Genre

Drama

11 'The Bridges of Madison County' (1995)

Appeared as Robert Kincaid

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.

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