2nd Most Badass Clint Eastwood Movie After Gran Torino Almost Cast Frank Sinatra Instead


Clint Eastwood’s decades-long acting career is bejeweled with some of the most memorable endeavors movie-goers have seen. He rose to top stardom with his spaghetti Westerns and kept offering audiences something exciting to look forward to with each release. One project in particular, which spanned multiple installments, birthed a genre-defining thriller and a performance by the leading star that was dubbed his career’s best at the time.

We are, of course, talking about Dirty Harry. Although not everyone embraced the film with open arms upon release, its long-lasting legacy endures despite debates around alleged problematic themes and undertones. It is currently one of the most well-known titles linked with Eastwood. People can’t fathom anyone else playing the part. However, like most renowned roles in pop culture history, Eastwood had to join a long line of actors considered for portraying the titular character.

Famous singer and actor Frank Sinatra was among the many deemed suitable for the role.

Dirty Harry Is Among Clint Eastwood’s Most Well-liked Endeavors

The neo-noir action thriller film, helmed by Don Siegel and eventually expanded into a film series, was released on December 23, 1971. The Dirty Harry story drew upon the real-life case of the Zodiac Killer. It featured the titular character, a no-nonsense police inspector, hunting down a psychopathic serial killer named Scorpio. The movie amassed $36 million against a budget of $4 million and was reckoned a blockbuster. Not only was the endeavor a commercial success, but it also reaped critical favor. However, the release wasn’t free of controversy.

While most reviewers were warm to the Siegel-directed project, others sparked a debate regarding Dirty Harry’s controversial undertones. Many people were disturbed by its violent content. Some couldn’t connect to the morally dubious characters. It was even banned in Finland for over a year! However, the most polarizing criticism came from critics like Roger Ebert, who stated, “The movie’s moral position is fascist. No doubt about it.” It also spurred discussions about police brutality and the role of law enforcers.

Despite such controversial reviews, Dirty Harry garnered an overall favorable reception, solidifying its standing in popular culture and film history. Siegel’s movie has an approval rating of 89% on Rotten Tomatoes and an audience score of 90%.

Its blockbuster stature prompted the production and release of follow-up installments, with the fifth and last being The Dead Pool (1988). Irrespective of what the consensus around the film is, Dirty Harry remains a certified Clint Eastwood classic.


But there was a minute chance of the now 93-year-old Hollywood actor and filmmaker never embodying Inspector Harry Callahan. Instead, Frank Sinatra would have charmed audiences in the iconic brown tweed sport coat.

Frank Sinatra Nearly Played Dirty Harry

Dirty Harry is widely regarded as Clint Eastwood’s career-defining role. However, before he could step into the shoes of the no-nonsense police inspector, other talents emerged as top contenders. Among such individuals were John Wayne, Steve McQueen, Robert Mitchum, Burt Lancaster, etc. One of the most prominent names and someone who best fit Callahan’s character profile was renowned singer and actor Frank Sinatra.

Alas, Sinatra, initially linked to the premise, departed the project. In an interview with MTV, Clint Eastwood was asked about the singer’s initial involvement with Dirty Harry. In response, the Gran Torino alum divulged the reason behind Sinatra’s exit. Following is what Eastwood commented:

“I guess they tried to get a lot of people for it. They tried Frank Sinatra, Robert Mitchum, and Steve McQueen. Then, they finally ended up with Frank Sinatra. I was in postproduction [on Play Misty for Me], and they called up and asked, ‘Are you still interested in Dirty Harry?’ I said, ‘What happened to Frank Sinatra?’ And they said, ‘Frank Sinatra’s got some problem with his hand, and he can’t hold a gun.’”

The Young at Heart alum couldn’t use the Dirty Harry gun because of his wrist injury. Eastwood called Sinatra’s reason for leaving “a pretty lame excuse.” After being approached for the part, the Unforgiven star set down one condition:

“I said, ‘I’ll do it.’ But since they had initially talked to me, there had been all these rewrites. I said, ‘I’m only interested in the original script.’ [The rewrites had changed] everything.”

That’s how Clint Eastwood landed one of his best-known roles. Given the number of individuals that were approached for the part initially, it seemed possible that it was a fated occurrence for the Million Dollar Baby star!

Dirty Harry (1971) is available for streaming on Amazon Prime Video.

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