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Dirty Harry is one of the most important roles in actor Clint Eastwood’s career. It helped further catapult Eastwood into megastardom, with a character that’s still quoted and referenced to this day. But as some know, the part was originally supposed to be singer Frank Sinatra’s to take, but he dropped out of the project.

When Eastwood later learned why Sinatra dropped out of Dirty Harry, the Oscar-winner thought it wasn’t a legitimate reason. But rather, it was an excuse.

Clint Eastwood was told a lot of actors rejected the role because of political reasons

Clint Eastwood smiling while wearing a suit.
Clint Eastwood | Michael Kovac/Getty Images

Eastwood wasn’t the first actor approached to play the hardened detective. Many actors, from Oscar-winner John Wayne to Paul Newman, were given the opportunity to crack the role. However, according to Eastwood, they eventually shied away from the part because of potential controversies.

“I was told when I first got the script that other actors had liked it but had reservations about the political elements of it,” Eastwood once told MTV News. “But even at that age, I was not afraid of it. To me, it was an exciting detective story. It was a fantasy. Here’s a guy who is so dogmatic that nothing is going to stop him when his mind is made up.”

Eastwood was aware that, because of the film’s controversies and political leanings, many critics had choice words for the movie. But that didn’t make Eastwood think any less of the film.

“I didn’t care less. Somebody else called it a fascist masterpiece,” he continued. “People are always calling people names, the great right-wing conspiracy or the great left-wing conspiracy. You make a movie, and if somebody reads something into it, then great, more power to him. [Director] Don Siegel and I were both very moderate politically. We didn’t think much of it. We just had a good time with it.”

Clint Eastwood called Frank Sinatra’s reasons for turning down ‘Dirty Harry’ a lame excuse

Frank Sinatra was another actor who was supposed to play the iconic detective. In fact, as far as Eastwood knew, Sinatra had already accepted the role. But he was later informed that complications prevented Sinatra from actually starring in Dirty Harry.

“I was in postproduction [on Play Misty for Me], and they called up and asked, ‘Are you still interested in Dirty Harry,’” Eastwood recalled. “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.’ That sounded like a pretty lame excuse, but it didn’t matter to me. 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 Cry Macho star insisted on the original because there were changes made to the first Dirty Harry story he didn’t agree with.

“They had marine snipers coming on in the end, and I said, ‘No. This is losing the point of the whole story, of the guy chasing the killer down. It’s becoming an extravaganza that’s losing its character,’” he elaborated.

Clint Eastwood didn’t believe ‘Dirty Harry’ could be made in today


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Eastwood doesn’t feel that today’s generation of audiences and cinephiles would’ve accepted Dirty Harry. That’s because, when compared to his time, Eastwood felt the more modern generation was a bit too soft.

“A lot of people thought it [Dirty Harry] was politically incorrect,” Eastwood said at the Cannes Film Festival (via Yahoo). “That was at the beginning of the era that we’re in now, where everybody thinks everyone’s politically correct. We’re killing ourselves by doing that.”

The J. Edgar director has long since held this belief about today’s generation. In an interview with Esquire, he expressed his thoughts even more candidly.

“We’re really in a p**** generation. Everybody’s walking on eggshells,” Eastwood said. “We see people accusing people of being racist and all kinds of stuff. When I grew up, those things weren’t called racist. Secretly everybody’s getting tired of political correctness, kissing up.”