All 5 Westerns Directed By Clint Eastwood, Ranked

Clint Eastwood's filmmaking efforts have been all over the map. Granted, from 2010 onward, his interests grew a lot narrower as he became infatuated with almost exclusively telling stories about modern American heroes, like the figures at the heart of "The 15:17 to Paris," "American Sniper," or "Sully." Still, for much of his career, he's shown an interest in various artistic passions. That's resulted in a filmography that's often been lauded by the general public and produced his best movies. When you're helming features for 50+ years, you're bound to churn out some bangers.

Shockingly, Westerns make up less of his filmmaking exploits than one might think. Despite Westerns being a cornerstone genre of Eastwood's acting resume and one of his most famous directorial efforts ("Unforgiven") belonging to this genre, Eastwood only directed five Westerns in his entire career. These motion pictures were released across all 50 years of his filmmaking tenure, hitting varied levels of artistic success. Ranking Clint Eastwood's Western directorial efforts from worst to best (based on their average Letterboxd ratings) exemplifies that even a confident director and Western veteran like this one couldn't crank out a winner every time.

Still, the best of Eastwood's Western directorial efforts (at least according to the Letterboxd crowd) make it apparent why this guy has such a towering reputation.

With 2024's "Juror #2," Clint Eastwood concluded a directorial career that started in 1971. His work behind the camera produced some big hits, as well as some deeply beloved artistic achievements. Unfortunately, Eastwood's filmmaking resume also includes some creative misfires that have largely been forgotten. Just before "Juror #2," Eastwood helmed the 2021 title "Cry Macho." Also playing the film's lead character, the legendary actor saddled up on a horse one more time for a title that's had far less staying power than the most revered Eastwood Westerns.

In this project, Eastwood played Mike Milo, a former rodeo fixture whose tasked with securing the son of his ex-boss from Mexico. Some Eastwood Westerns excel as maximalist entertainment. Others are contemplative ruminations on both the genre and human nature. "Cry Macho," alas, didn't work on either of those fronts. With an average Letterboxd rating of 2.8, most found this motion picture to be pretty forgettable. Eastwood's last time directing a Western was routinely criticized for lacking interesting characters and phoned-in visuals. The specificity littering earlier Eastwood directorial efforts in this genre was tragically absent.

That 2.8 rating does indicate some Letterboxd users found plenty to enjoy in "Cry Macho." By and large, though, this was a disposable Western that, thankfully, wasn't the final note of Eastwood's entire directorial career. "Juror #2" was a much better send-off.

As a bunch of lowly gold miners are attacked by men hired by the wealthy Coy LaHood (Richard Dysart), it's clear that the world of "Pale Rider" is off its moral axis. Luckily, "Preacher" (Clint Eastwood) soon strolls in to dish out justice. Things get more complicated, though, once LaHood insists on dishing out Marshall Stockburn (John Russell) to take care of these problems and Preacher. While the golden age of Western cinema was already a distant memory once "Pale Rider" hit theaters in 1985, it nevertheless existed in a decade that still produced some genre-defining Westerns. 

"Pale Rider" and its streamlined plot of Preacher protecting vulnerable gold miners has garnered a respectable enough reputation as another solid foray into the '80s Western domain. On Letterboxd, it has a 3.6 average rating, with many of the site's reviewers noting that Eastwood's filmmaking chops add extra juice to the proceedings. A little over a decade into his filmmaking career, his visual instincts were razor-sharp and ensured that the rowdiest "Pale Rider" set pieces sung. 

The distinctive costume design and memorable supporting performances were also highlighted as virtues across its Letterboxd entries. While not garnered as the next "The Good, The Bad, and the Ugly," "Pale Rider" still stands tall with its Western mayhem.

In 1971, the thriller "Play Misty for Me" marked the first time Clint Eastwood stepped behind the camera as a director. This was a project decidedly set in the modern world (Eastwood played a radio DJ) showing that he could anchor projects other than spaghetti Westerns. For his second filmmaking endeavor, 1973's "High Plains Drifter,", Eastwood returned to the cinematic field that launched him to stardom. It also marked the inaugural time Eastwood directed a Western, though it clearly wouldn't be the last.

Here, Clint Eastwood played The Stranger, whose hired by the folks of Lago to use his skills for killing to fend off a trio of criminals arriving to the territory. With an average 3.7 rating on Letterboxd, "High Plains Drifter" is held in solid regard by Letterboxd users, many of whom expressed shock over how brutal this title is. Anyone expecting a rootin'-tootin' escapist adventure is in for a jarring experience given how much Eastwood's The Stranger is depicted as terrifyingly as the "villains." 

This is the kind of moody Western fans of modern titles like "The Power of the Dog" need to see. Committing to that grim tone and some tremendous camerawork for the grisliest sequences didn't just guarantee "High Plains Drifter" a solid Letterboxd score. It also reaffirmed Eastwood as a filmmaking force of nature to look out for.

As early as the 1970s, Clint Eastwood was already playing around with the staples of the genre that birthed his movie star persona. "The Outlaw Josey Wales" is a must-watch '70s Western that still holds up today, poking the boundaries of what Westerns could be. In this title, Eastwood portrayed the titular Josey Wales, a Confederate Army soldier who recruits himself to avenge his murdered family. The Civil War eventually concludes, but the bloodthirsty Wales is still being hunted down. That becomes a problem once he begins attracting various societal misfits around him, who could find a bullet in their heads given how much violence follows Wales.

On Letterboxd, "The Outlaw Josey Wales" has a sterling 3.9 average rating. Among its fans is none other than "Mission: Impossible- Fallout" helmer Christopher McQuarrie, who penned a lengthy Letterboxd entry waxing poetic on the film's virtues, including how it subverts standards of typical revenge-oriented action films. He's certainly not alone in that effusive praise given that so many other Letterboxd reviews also heap positive marks on "The Outlaw Josey Wales," with its evocative atmosphere and impactful images especially getting shout-outs.

With "The Outlaw Josey Wales," Eastwood demonstrated that he could subvert audience expectations both in front of and behind the camera. The American Western wasn't content to rehash the genre's greatest hits.

Clint Eastwood continued directing movies of all genres for more than three decades after "Unforgiven" hit theaters. However, in many ways, this particular Western feels like the culmination of his entire career. Now older and wearier, Eastwood believably imbued regret and hard-earned wisdom into this particularly mournful Western. In "Unforgiven," the figures making up Old West myths aren't sacrosanct heroes, but vulnerable men haunted by the carnage they've dished out. If prior Eastwood Western directorial efforts dabbled in being revisionist Westerns, then "Unforgiven" went all in on this aesthetic to tremendous results.

Here, Eastwood played William Munny, a legendary slaughterer of human beings whose since turned into a farmer. When an opportunity to raise some cash for his kids arises, he reluctantly returns to the bounty hunter profession, which leads to him confronting the corrupt Sheriff "Little" Bill Daggett (Gene Hackman). Given the movie's tremendous Oscars success and influence on future projects like Taylor Sheridan's "Yellowstone,"  it's no surprise this title has an impressive 4.2 average Letterboxd rating. Many users especially hail Eastwood's commitment to a grim tone that effectively captures the bleak world Munny and his fellow Old West inhabitants live in.

Most reviews also note that this feature contains some of Gene Hackman and Morgan Freeman's greatest work. No wonder "Unforgiven" is the quintessential and creative peak of Eastwood's entire directorial career.