Clint Eastwood’s 5 Worst Western Movies, Ranked

Clint Eastwood’s film career includes major awards, enduring box-office successes, and collaborations with some of cinema’s most respected performers. Still, no matter how far his work has extended beyond the genre, Eastwood remains inseparable from the Western. His breakthrough came as the Man With No Name in the 1960s, followed by films such as “The Outlaw Josey Wales,” which confirmed his natural command of the frontier setting. With the darker, reflective “Unforgiven” in 1992, Eastwood cemented his status as the genre’s leading figure outside the John Wayne tradition.

That reputation does not mean every Eastwood Western was a classic. Considering the number of films he led, a few disappointments were inevitable. Alongside his celebrated Westerns—many of which rank among the genre’s finest—are five lesser entries, ranked from least disappointing to worst according to their average Letterboxd ratings. Looking back at these films offers an intriguing snapshot of how Eastwood’s Western career developed over the decades.

None of these movies is likely to appear on a list of essential Westerns. Even so, they reveal just how extensively Eastwood explored the genre that ultimately became his cinematic trademark.

Ben Platt playing a teenager in “Dear Evan Hansen.” The original “Rent” cast reuniting for the film version despite having long outgrown their characters. James Corden’s much-discussed work in “Cats.” Movie-musical history is filled not only with beloved classics but also with casting decisions that left audiences wondering who approved them. One of the strangest examples is Clint Eastwood taking a starring role in the Western musical “Paint Your Wagon.”

Eastwood had already established himself as the hard-edged Man With No Name in ambitious spaghetti Westerns such as “The Good, the Bad and the Ugly,” films that challenged conventional Hollywood formulas. His sudden appearance at the center of a traditional studio musical was therefore difficult to understand. The decision was even more questionable because Eastwood was hardly celebrated as a singer. Set during the California Gold Rush, the film follows men competing to purchase Elizabeth Woodling (Jean Seberg), the wife of a Mormon. This wildly unconventional production holds a 3.2 average rating on Letterboxd, although some viewers admire its fearless commitment to excess.

For most viewers, however, the spectacle of Lee Marvin and Eastwood singing their way through the Old West could not justify a 164-minute running time. The film has at least enjoyed a second life through a memorable “Simpsons” joke many years after its release.

In “Joe Kidd,” the title character has supposedly left his bounty-hunting past behind. As Western heroes often discover, though, old lives have a way of returning. Frank Harlan (Robert Duvall) pressures Kidd into tracking down Luis Chama (John Saxon), sending him back into the saddle and into a series of confrontations across the frontier. The film had an impressive creative lineup: John Sturges, director of “Bad Day at Black Rock” and “The Great Escape,” was behind the camera, Elmore Leonard wrote the screenplay, and Lalo Schifrin supplied the score.

That combination of talent suggested the possibility of a major Western, but “Joe Kidd” developed a far quieter reputation. Its 3.2 Letterboxd average indicates that it has supporters, yet many viewers consider it merely adequate. The most frequent criticism is aimed at a screenplay that never gives the story much individual character or momentum.

For some Letterboxd users, the film’s cast and crew mainly served as reminders of stronger work by the same artists. “Joe Kidd” is not unbearable, but it falls well short of the essential Westerns that fans consider required viewing.

The films most often cited as Clint Eastwood’s finest do not tell the whole story of his career. He began working in movies during the 1950s, including the Western comedy “The First Traveling Saleslady.” The Ginger Rogers vehicle centers on Rose Gillray, a corset entrepreneur who attempts to rebuild her business and pay off debts by selling steel wire to Texas cattle ranchers. During her journey, she meets colorful figures including Lieutenant Jack Rice, played by Eastwood, while Barry Nelson portrays her eventual romantic interest, Charles Masters.

Seeing Eastwood as a supporting performer in an ensemble comedy is unusual enough, especially when compared with the stern, commanding Western persona he would later develop. “The First Traveling Saleslady” also places him in a broad, joke-heavy setting that feels far removed from his usual screen image. That novelty makes the film worth noting for fans, but its 3.0 Letterboxd average reflects its shortcomings. Flat characters, dated and uncomfortable gender politics, and weak humor have all contributed to its poor reputation.

The most animated Letterboxd reactions often come from viewers surprised to learn that Eastwood appears in the movie at all. That discovery may be entertaining, but it cannot carry an entire feature. “The First Traveling Saleslady” remains more of an Eastwood curiosity than a satisfying film in its own right.

Eastwood has been unusually candid about his dislike of “Ambush at Cimarron Pass,” the 1958 Western directed by Jodie Copelan. Running just 73 minutes, the film stars Scott Brady as Sergeant Matt Blake, a soldier who joins forces with cowboys while crossing dangerous territory controlled by Indigenous people. Eastwood plays Keith Williams, with Margia Dean appearing as Teresa Santos, the story’s main female character. Eastwood was so disappointed by the production—and by his own performance—that he once feared it might end his acting career. Instead, he would remain in the Western world and eventually find considerably greater success.

Viewers who have sought out “Ambush at Cimarron Pass” generally understand Eastwood’s harsh assessment. Its 2.9 Letterboxd average reflects complaints about the film’s visibly limited budget. While financial constraints can sometimes encourage inventive filmmaking, here they result in a production that looks cheap and lifeless. Critics have also pointed to rigid performances and Copelan’s lack of visual energy.

What prevents “Ambush at Cimarron Pass” from sinking even lower among Letterboxd’s worst Westerns is the unusual chance to watch Eastwood at the very beginning of his career. That historical interest, however, does little to make the film itself compelling—a conclusion Eastwood reached long ago.

Eastwood has directed numerous acclaimed movies, but his filmmaking became noticeably less energetic in the 2010s. Films such as “Jersey Boys” and “The 15:17 to Paris” were criticized for their muted gray visuals and cautious storytelling. Even strong performers including Paul Walter Hauser and Sam Rockwell struggled to bring momentum to 2019’s “Richard Jewell.” The vivid violence and force of Eastwood’s early Westerns seemed increasingly distant from the subdued style of his later directorial work.

That criticism also followed “Cry Macho,” the 2021 film in which Eastwood plays former rodeo rider Mike Milo, who travels to Mexico to bring home his ex-boss’s son. With a 2.8 average rating on Letterboxd, the movie was often described as slow-moving, visually basic, and burdened by unnatural dialogue. Several viewers also found its conclusion overly calculated and predictable. Others, however, appreciated the film’s relaxed pace and gentle mood as an alternative to the louder, faster style common in contemporary cinema.

Overall, “Cry Macho” received little of the broad acclaim associated with Eastwood’s earlier work. Its return to the Western was fitting, particularly as one of his final filmmaking projects, but the familiar setting was not enough to overcome the concerns that shaped the film’s largely lukewarm Letterboxd reception.