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

Clint Eastwood with a horse in Cry Macho
Image via Warner Bros.

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 16, 2021
Director
Clint Eastwood
Cast
Clint Eastwood , Dwight Yoakam , Fernanda Urrejola , Brytnee Ratledge , Horacio Garcia Rojas , Paul Alayo
Runtime
125
Main Genre
Drama

29 'Every Which Way but Loose' (1978)

Appeared as Philo Beddoe

Clint Eastwood driving while his pet orangutan flips someone off from the passenger seat in Every Which Way but Loose
Image via Warner Bros.

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.

Every Which Way But Loose
PG
Comedy
Action

Release Date
December 20, 1978
Director
James Fargo
Cast
Clint Eastwood , Sondra Locke , Geoffrey Lewis , Beverly D'Angelo
Runtime
114 minutes

Rent on Apple TV

28 'Sully' (2016)

Directed by Clint Eastwood

Tom Hanks as Sully with wind blowing on his face while looking to the distance in Sully.
Image via Warner Bros. Pictures

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

Clint Eastwood and Anjelica Huston in Blood Work
Image via Warner Bros.

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
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

Clint Eastwood standing at a marina looking at someone off screen in Magnum Force

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.

Magnum Force (1973)
R

Release Date
December 25, 1973
Director
Ted Post
Cast
Clint Eastwood , Hal Holbrook , Mitchell Ryan , David Soul , Felton Perry , Robert Urich
Runtime
123 minutes

Rent on Apple TV

25 'Play Misty for Me' (1971)

Appeared as Dave Garver

Clint Eastwood looking forward at someone while sitting at a bar with Jessica Walker behind him in Play Misty for Me
Image via Universal Pictures

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.

Play Misty for Me
R
Psychological
Thriller
Release Date
October 20, 1971
Director
Clint Eastwood
Cast
Clint Eastwood , Jessica Walter , Donna Mills , John Larch
Runtime
102

Watch on Netflix

24 'Two Mules for Sister Sara' (1970)

Appeared as Hogan

Two Mules for Sister Sara - 1970
Image via Universal Pictures

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
GP
Where to Watch

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Release Date
May 28, 1970
Director
Don Siegel
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.

Rent on Apple TV

22 'Kelly's Heroes' (1970)

Appeared as Kelly