Clint Eastwood’s 5 Worst Western Movies, Ranked from Bad to Worst

Clint Eastwood’s career has included Oscar victories, major box-office successes and collaborations with some of cinema’s most respected performers. Still, even Eastwood would likely acknowledge that his public image remains inseparable from the Western. His breakthrough came as the mysterious Man With No Name in the spaghetti Westerns of the 1960s, and movies such as “The Outlaw Josey Wales” confirmed his natural authority in the genre. With the darker, more reflective “Unforgiven” in 1992, Eastwood cemented his reputation as one of the defining Western stars of the modern era—perhaps the genre’s most prominent leading man after John Wayne.

That iconic status does not mean every Clint Eastwood Western was a triumph. Considering the number of films he headlined, a few misfires were inevitable. Alongside his most celebrated Westerns—many of which rank among the genre’s essential classics—are five less successful entries, ranked here from the least disappointing to the weakest according to average Letterboxd ratings. Looking back at these movies offers an intriguing view of how audiences have assessed the less polished corners of Eastwood’s Western filmography.

None of these films is likely to appear on a list of the greatest Westerns ever made. Even so, they demonstrate just how extensively Eastwood worked within the genre that ultimately became his cinematic trademark.

Movie musicals have never been short of baffling casting decisions, from Ben Platt playing a high school student in “Dear Evan Hansen” to the original “Rent” cast returning for the film long after aging out of their roles. James Corden’s work in “Cats” also remains a frequent source of bewilderment. Among the more surprising examples is Clint Eastwood taking a leading role in the Western musical “Paint Your Wagon.”

Eastwood had already become famous for playing the enigmatic Man With No Name in bold, revisionist spaghetti Westerns such as “The Good, the Bad and the Ugly.” Against that background, seeing him headline a traditional Hollywood musical felt especially strange. The casting was even harder to understand given that Eastwood was not known for his singing voice. Set during the California Gold Rush, “Paint Your Wagon” follows men competing to purchase Elizabeth Woodling (Jean Seberg), the wife of a Mormon. The 164-minute film currently holds a 3.2 average rating on Letterboxd, although some viewers appreciate its fearless commitment to its wildly unconventional concept.

For many others, however, watching Eastwood and Lee Marvin sing their way through the Old West was not enough to justify the movie’s lengthy running time. “Paint Your Wagon” has nevertheless lived on through its memorable afterlife in pop culture, including a memorable “The Simpsons” joke years after its release.

In “Joe Kidd,” the title character believes his days as a bounty hunter are behind him. As Western heroes often discover, though, the past has 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 another series of shootouts across the frontier. The film brought together an impressive creative team: John Sturges, director of “Bad Day at Black Rock” and “The Great Escape,” Elmore Leonard as screenwriter and Lalo Schifrin providing the score.

With that much talent involved, “Joe Kidd” seemed positioned to become a major Western. Instead, its reputation has remained relatively muted compared with the genre’s most acclaimed films. Its 3.2 Letterboxd average indicates that the movie still has supporters and works as a straightforward entertainment for some viewers. Many critics on the platform, however, describe it as merely adequate, pointing to a script that lacks a distinctive voice.

For some Letterboxd users, the film’s accomplished cast and crew mainly highlighted the stronger movies those artists had made elsewhere. “Joe Kidd” is not necessarily painful to watch, but its routine storytelling keeps it well below the essential Westerns that serious fans are encouraged to see.

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Eastwood’s best-known films represent only part of his long screen career. He began acting in the 1950s, including a supporting appearance in the Western comedy “The First Traveling Saleslady.” The Ginger Rogers vehicle stars her as Rose Gillray, a corset-business owner who attempts to rebuild her company and pay off debts by selling steel wire—a vital corset material—to Texas cattle ranchers. During her journey, she crosses paths with Lieutenant Jack Rice, played by Eastwood, while Barry Nelson portrays her eventual love interest, Charles Masters.

For audiences accustomed to seeing Eastwood dominate a Western, his role as one member of a larger comic ensemble in “The First Traveling Saleslady” can feel unusual. So too can the idea of the typically stoic star appearing in a broad, joke-heavy comedy. That novelty may interest dedicated Eastwood fans, but the film’s 3.0 Letterboxd average reflects its limited appeal. Flat characters, dated and troubling gender politics, and weak humor all contribute to its lackluster reputation.

The most enthusiastic Letterboxd reactions often come from viewers surprised to learn that Eastwood appears in the movie at all. That discovery makes for an amusing piece of trivia, but it cannot carry an entire film. “The First Traveling Saleslady” ultimately fails to stand out on its own merits.

Eastwood has been 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, who joins forces with cowboys while attempting to survive hostile territory controlled by Indigenous people. Eastwood appears as Keith Williams, with Margia Dean playing Teresa Santos, the story’s principal female character. Disappointed by the movie and unhappy with his own performance, Eastwood once feared the experience might force him to give up acting altogether. Fortunately, he would go on to find considerably greater success in the Western genre.

The small number of viewers familiar with “Ambush at Cimarron Pass” generally share Eastwood’s negative assessment. Its 2.9 average Letterboxd score reflects complaints about the movie’s visibly limited budget. Low resources can sometimes encourage inventive filmmaking, but here they mostly leave the production looking drab and underdeveloped. Reviewers have also criticized the stiff acting and Copelan’s lack of visual energy.

What prevents “Ambush at Cimarron Pass” from sinking even lower among Letterboxd’s worst-rated Westerns is the curiosity of watching Eastwood at such an early stage of his career. Even that historical interest, however, cannot transform the film into a particularly engaging Western.

Eastwood has directed many outstanding films, but his output became noticeably more restrained and sluggish during the 2010s. Movies such as “Jersey Boys” and “The 15:17 to Paris” were marked by muted gray visuals and few bold creative decisions. Even strong performers, including Paul Walter Hauser and Sam Rockwell, could not fully rescue the plodding “Richard Jewell” in 2019. The energetic violence and visual flair of Eastwood’s spaghetti Westerns had largely given way to a much flatter late-career style.

That criticism followed “Cry Macho,” his 2021 drama about former rodeo star Mike Milo, who travels to Mexico to bring his former employer’s son home. The movie earned a 2.8 average rating on Letterboxd, with viewers objecting to its basic visual design and unnatural dialogue. Several reviewers also found the ending overly manipulative and easy to predict. Others, however, welcomed the film’s relaxed pace and understated warmth as an alternative to the noisy spectacle of many contemporary releases.

Overall, “Cry Macho” received nowhere near the widespread acclaim associated with Eastwood’s earlier work. It was fitting that one of his final directing projects returned him to the Western, the genre that launched and defined his career. Unfortunately, that sense of closure was not enough to earn the 2021 film a stronger critical response on Letterboxd.