Clint Eastwood’s Best Role Was Nearly Snatched Away by Frank Sinatra

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After coming out of his Spaghetti Western era, Clint Eastwood may not have been able to reach true greatness without the support of Dirty Harry in the 1970s.

Clint Eastwood may not hold the youthful charm he once did in the 1950s or be the leading star of Spaghetti Westerns, but the Eastwood name can never be replaced as long as Hollywood stands. The movie star and cowboy actor of the century transitioned perfectly from the old talkies to the 21st-century Oscar-winner Million Dollar Baby without breaking a sweat.

Meanwhile, the industry stepping out of its Western fixation failed to outgrow and catch up to the rapidly transforming world outside. Their inability to adapt to the changing times and customs posed a huge red flag for the industry, marking the end of an era. Gone were the days of simplicity when all that the audience was curious about was if Frank Sinatra really had connections with the mob. The 1970s were all about the neo-noir classics and action thrillers.

Frank Sinatra vs Clint Eastwood: An Old Rivalry

While Hollywood flows through the ages, marking and highlighting each phase of cinematic evolution, the relationship between two rival actors coming up at the same time against the same audience can never be understated. Frank Sinatra‘s presence and ever-increasing popularity throughout the 50s and 60s earned him somewhat of a stink-eye from Clint Eastwood himself.

However, the situation took a turn when Ol’ Blue Eyes began to be courted for lead roles in major pictures, instead of the usual thoroughfare that concerned Eastwood. No longer was Hollywood a territory to be shared among actors like Paul Newman or Steve McQueen. The Sultan of Swoon claimed his stake in the business as well.

But while Sinatra had a flourishing music industry to fall back on, the identity of Clint Eastwood was utterly solidified as an actor. And the difference between these two identities becomes most obvious when one of them can turn down roles with shallow indignance while the other strives toward molding the role in the best manner possible to make a movie successful.

Frank Sinatra Almost Pushed Clint Eastwood Out of a Job

In the 1960s, California was plagued by the infamous Zodiac killer who terrorized the town for years without ever getting caught, despite sending letters taunting the police. Logically, the premise would be the plot and premise of a great noir in the making if it wasn’t so already real. Scripts were being developed in Hollywood and passed down to agents and developers.

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Soon enough, the role landed at the doorstep of Frank Sinatra, whose 1954 Oscar win gave him enough credibility to play a cop with conviction in the gritty neo-noir thriller. The film, on the other hand, was mutated to fit its Hollywood billing better, considering how the industry might be viewed as tone-deaf to be making a movie inspired by the Zodiac killings so soon after the real incidents. The new and improved title then became Dirty Harry.

Screenwriter John Milius tailormade the role for Sinatra after meeting the actor-singer at Warner Bros. However, William Friedkin, who was attached as the director for the film and had been involved in its preproduction, revealed, “We had prepared that for about six months, and then Sinatra pulled out. And the project was dead [so] we left…”

Later, actor Robert Davi divulged the real reason in an interview with Express UK, claiming [via Collider]:

[Milius] brought the .357 Magnum with him to show Sinatra. They were telling him the story and they go, ‘And this is going to be your gun’. And Sinatra picked up the gun and said, ‘I’m afraid it’s a little too big for my hands’ and that’s why he turned it down.

Although the reality behind the rejection was far more complicated than mere vanity, the story eventually floated down through the roster of available action stars and was turned down at every turn, including John Wayne, Robert Mitchum, Burt Lancaster, Steve McQueen, and even Paul Newman, before Clint Eastwood came into the picture (at Newman’s referral).

Decades later, it almost seems impossible to imagine anyone other than Eastwood in the titular role of Dirty Harry. The actor, through a few changes to the scripts, made the role so completely his that it has now become the most recognized role of Eastwood beyond the Dollars Trilogy from the 60s.

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