Clint Eastwood Has Frank Sinatra to Thank for ‘Dirty Harry’: Here’s Why

by Matthew Wilson
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Frank Sinatra really made Clint Eastwood‘s day, and year, and also career. The legendary singer was in line to play Detective Harry Callahan. Moving away from westerns, Eastwood then swooped-in for the now-iconic role.

It’s hard to imagine anyone else wielding the .44 Magnum revolver. Alongside the Man With No Name, Callahan became one of the two roles that defined the icon’s career. But in an alternate universe, the “My Way” singer stepped into the detective role instead.

Director William Friedkin almost directed the film with Sinatra in the leading role. Friedkin, known for films like “The Exorcist,” discussed one of cinema’s what-ifs. Speaking on Alec Baldwin’s podcast “Here’s the Thing,” Friedkin pondered his time in development on the project.

“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.’”

Sinatra backed out of the role due to a hand injury. Sinatra experienced a broken wrist while filming “The Manchurian Candidate” eight years prior. Though his wrist healed, he couldn’t put a lot of weight on it. The singer found he was literally unable to hold the weight of the .44 Magnum revolver comfortably. He bowed out of the project.

Clint Eastwood Replaces Frank Sinatra

Eastwood and director Don Siegel came in to replace both Friedkin and Sinatra on the story. Upon release, “Dirty Harry” proved to be massively successful with audiences. It also spawned one of cinema’s most iconic lines with the “Make my day, punk.”

Eastwood later went to star in four sequels to the film: “Magnum Force” (1973), “The Enforcer” (1976), “Sudden Impact” (1983), and “The Dead Pool” (1988).

Meanwhile, Sinatra was less fortunate. Audiences may not remember, but the singer had a successful film career as well. He won an Oscar for his role in 1953’s “From Here to Eternity,” and was nominated once more for 1955’s “The Man with the Gold Arm.” In the 1960s, he continued to find work, turning a great performance in the aforementioned “The Manchurian Candidate.”

But the singer’s acting career began to dry up in the 1970s. He played in the “Western Dirty Dingus Magee,” which was savaged by critics and audiences alike. These days Sinatra is more remembered for his songs and voice than his acting chops. Meanwhile, Eastwood has had a long and prosperous acting career.

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