Remember How Frank Sinatra Almost Played Dirty Harry?

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Clint Eastwood as the title character in the 1971 film ‘Dirty Harry’ (AP Photo/Warner Bros.)

Dirty Harry’s vigilante police detective Harry Callahan is one of the defining roles of Clint Eastwood’s career — but it was meant to be played by Frank Sinatra. In an interview for Alec Baldwin’s podcast Here’s the Thing, director William Friedkin (The French Connection, The Exorcist) revealed that he’d spent months developing the gritty 1971 crime drama with the crooner-turned-actor in mind.

“My producer, a guy named Phil D’Antoni, he and I were going to do Dirty Harry with Frank Sinatra,” said Friedkin. “And we had prepared that for about six months and then Sinatra pulled out. And the project was dead [so] we left and did The French Connection.” (While Sinatra’s involvement with Dirty Harry is well-documented, Friedkin’s connection to the film has rarely been discussed.)

Sinatra is said to have dropped out of Dirty Harry because of an injury. According to the book Gods Like Us: On Movie Stardom and Modern Fame by film critic Ty Burr, “a broken wrist sustained during The Manchurian Candidate eight years earlier meant that Old Blue Eyes couldn’t hold the heavy Magnum pistol comfortably.” However, the film — all about a heroic rogue cop who refused to follow the rules, leading Newsweek to call it “a right-wing fantasy” —would have lined up with Sinatra’s increasingly right-leaning political beliefs. In 1970, former Democrat Sinatra, reportedly shaken by the Kent State massacre, announced that he was backing Ronald Reagan for governor. He remained a staunch supporter throughout Reagan’s presidency.

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Frank Sinatra in the 1962 thriller ‘The Manchurian Candidate’

After Sinatra and Friedkin left Dirty Harry behind, the film was made by director Don Siegel with Clint Eastwood in the title role. The movie was a huge hit, and Eastwood went on to star as Callahan in four sequels: Magnum Force (1973), The Enforcer (1976), Sudden Impact (1983), and The Dead Pool (1988).

Meanwhile, the fifty-something Sinatra opted to play another anti-hero with “dirty” in front of his name: the title role in the 1970 comic Western Dirty Dingus Magee, which was ignored by audiences and blasted by critics. In retrospect, Dirty Harry seems like a missed opportunity for Sinatra, whose acting career began to peter out in the 1970s. Though best remembered as a singer, Sinatra had a long and accomplished film resume, including his Oscar-winning performance in 1953’s From Here to Eternity, his harrowing, Oscar-nominated turn as a heroin addict in 1955′s The Man With the Golden Arm, and his acclaimed performance in the 1962 thriller The Manchurian Candidate.

As for Friedkin, he made a different movie about a corrupt police officer: The French Connection, which won the Academy Awards for Best Picture, Best Director, Best Actor (Gene Hackman), and Best Adapted Screenplay in 1972. Years later, Friedkin still sees a connection between the film he made and the film he didn’t. “Those of us who made films in the ‘70s were not following the zeitgeist: we shaped it,” Friedkin wrote in a 2008 essay for The Guardian. “We no longer believed in a man on a white horse. We knew he was flawed because we were flawed. Dirty Harry would shoot a suspect in cold blood and audiences would applaud. When Popeye Doyle shot the French hitman in the back in my film The French Connection, audiences around America stood and cheered.”