The iconic Clint Eastwood role that Frank Sinatra turned down: “A darn good script”
Some actors are easy to mix up. Bryce Dallas Howard and Jessica Chastain, for example. The many Chrises of the Marvel Cinematic Universe. Tilda Swinton and David Bowie. Then, there are the actors who hold similar places in the film industry. Michael Cera and Jesse Eisenberg could easily trade places in most movies. Liam Neeson and Denzel Washington have both cornered the market for over 60 action heroes. And Joan Crawford and Bette Davis could have swapped any of their roles in the latter half of their careers.
When it comes to Clint Eastwood, there were several analogous celebrities, especially early in his career. He was a western icon in the mould of John Wayne, albeit of an entirely different generation. He and Burt Reynolds were often up for the same roles, and by the time he’d switched to action movies like Dirty Harry, he could easily be compared to other lethal silent types like Charles Bronson and Kurt Russell.
You could imagine Eastwood, Bronson, and Russell vying for the same roles. It isn’t hard to mentally replace Bronson with Russell in Death Wish or Russell with Eastwood in Escape from New York. One actor who absolutely doesn’t come to mind alongside these actors is Frank Sinatra. The 1940s crooner and Rat Pack progenitor was not really known for taking the counterculture by storm.
You could imagine him smoking cigars with the latest Mafia don at a casino while wearing a tux, but it’s harder to imagine him smoking weed with Dennis Hopper on a beach in Malibu with his shirt off. And yet, there was one film that only went to Eastwood because the ‘Fly Me to the Moon’ singer turned it down.
Dead Right was a script by Harry Julian Fink and Rita M Fink about a cop named Harry Callahan who is so determined to catch a serial killer that he takes the law into his own hands. Eventually retitled Dirty Harry, it became Eastwood’s most iconic character aside from The Man with No Name. Originally, however, the studio had other actors in mind. They went to Paul Newman first, but he turned it down, believing it to be too right-wing.
Then, they went to Sinatra, who loved it at first. In a 1970 interview, the singer said that he was planning to shoot the film in San Francisco and was very excited about it. “It’s a marvellous script,” he said, revealing that filming would begin in a matter of months. It had originally been set in New York, he explained, but he himself had requested the change to San Francisco. “I don’t think it’s ever been photographed as well as it should be,” he explained. “It’s a darn good script, it really is. Great suspense.”
Shortly thereafter, however, Sinatra backed out. He claimed it was because he broke his wrist while filming The Manchurian Candidate and would therefore be unable to lift the heavy magnum pistol that Harry wields, but Eastwood’s biographer, Marc Eliot, asserts that it was more likely that the singer got cold feet about playing such an unsympathetic character.
Whatever the reason, Sinatra’s exit allowed Eastwood to take his place, and the rest is history. He was more than willing to inhabit a nasty character, and he did so with such swagger and conviction that it led to four more films.
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