Why Clint Eastwood Stopped Making Westerns With Sergio Leone

Yahoo Entertainment

By Joe Roberts

April 1, 2026

Sergio Leone's "Dollars" trilogy reinvigorated Westerns and turned Clint Eastwood into a star. But after making three films with Leone, Eastwood simply wasn't interested in recycling the Man with No Name and had grown tired of the director's approach to filmmaking.

Eastwood is the kind of screen legend they simply don't make any more. But without Leone he might never have ascended to the heights he ultimately did. With his "Dollars" trilogy, the Italian filmmaker transformed Eastwood from ramrod Rowdy Yates on CBS's "Rawhide" into the gruff, laconic Man with No Name. Though it took some time for the "Dollars" trilogy to be released in the United States, and initial reviews weren't exactly glowing, "A Fistful of Dollars, "For a Few Dollars More," and "The Good, the Bad and the Ugly" ultimately gave Eastwood a movie career.

How did Eastwood feel about his "Dollars" trilogy? Well, as detailed in the book "Clint Eastwood: Interviews, Revised and Updated"," he viewed the films as "satire" — sendups of both the Western and the Akira Kurosawa movies on which they were based. Nonetheless, he was both grateful and had great respect for his three Spaghetti Westerns, even if he wasn't interested in making any more.

Sergio Leone tried to recruit Clint Eastwood for a gangster epic

After Sergio Leone finished rewriting the rules of filmmaking with 1966's "The Good, the Bad and the Ugly," he envisioned making several more movies with Clint Eastwood. But Leone didn't necessarily want to continue the saga of the Man with No Name. In fact, his first post-"Dollars" trilogy idea revolved around the writer Herschel Goldberg, aka Harry Grey, whose book "The Hoods" had inspired the director. The semi-autobiographical novel focused on Jewish-American organized crime during the Prohibition era, but Leone wanted to expand the story into something more broad; an exploration of American gangsterism in general.

There was only one man Leone wanted for the project: Eastwood. The director envisioned his "Dollars" trilogy star as playing an Irish gangster, but without a script or even a treatment, the actor himself was less than enthusiastic. Eastwood recalled the never realized project in a post from the official Clint Eastwood Archives, "He had this idea about doing a gangster movie. He said, 'What about Irish gangsters? You could play an Irish gangster.'" But the idea never evolved into anything more — at least it didn't do so quickly enough for Eastwood. "It was always just there," he added, "always hanging there."

Ultimately, the actor wasn't interested in something barely-even half-formed. "I like to know the joke," he said. "I don't want someone to tell me a joke and not give me the punch line." With his star non-committal, Leone moved away from the gangster epic idea and drifted back towards Westerns. But the director hadn't given up on re-teaming with the leading man of his "Dollars" trilogy and tried to secure Eastwood's services for his new vision. Alas, the actor had many of the same reservations.

Clint Eastwood walked away from Sergio Leone after The Good, the Bad and the Ugly

Clint Eastwood's decision to star in 1964's "A Fistful of Dollars" was an easy one. In "Clint Eastwood: Interviews, Revised and Updated," the actor is quoted as saying, "I had nothing to lose. I had a job waiting in TV and I knew if it was a flop nobody would ever see it anyway." But by the time Leone started developing follow-up Westerns, Eastwood had evolved. Now a major star with specific preferences, the actor was uninterested in making any more Westerns with Leone if it meant rehashing the "Dollars" trilogy or entertaining the director's extemporaneous approach to movie-making (even the idea behind "The Good, The Bad, and The Ugly" was improvised).

After abandoning his Irish gangster idea (at least for the time being) Leone moved on to developing 1968's "Once Upon a Time in the West" and 1971's "Duck, You Sucker!" Eastwood wasn't interested. According to FarOut magazine, the actor said, "They were just repeats of what I'd been doing. I didn't want to play that character anymore." In "Conversations with Clint: Paul Nelson's Lost Interviews with Clint Eastwood, 1979-1983" the actor elaborated on how Leone's interests diverged from his own:

"[Leone] wanted to go more into a kind of spectacle thing. I think Leone more envisioned himself as a David Lean à la Italiano, and that's understandable. He just wanted to make bigger, more elaborate projects."

Ultimately, Charles Bronson ended up playing the role meant for Eastwood in "Once Upon a Time in the West." After the follow-up, "Duck! You Sucker," Leone finally brought his gangster epic to fruition with 1984's "Once Upon a Time in America," sans Eastwood, who that same year starred in a terrible gangster movie that Roger Ebert absolutely hated.