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Clint Eastwood

Clint Eastwood Once Called Frank Sinatra’s Reasons for Turning Down ‘Dirty Harry’ a ‘Lame Excuse’

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

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.”

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Clint Eastwood

Dirty Harry: 5 Ways He’s Clint Eastwood’s Best Character (& 5 Alternatives)

After starring in Don Siegel’s gritty police thriller Dirty Harry, Clint Eastwood reprised the title role of Inspector “Dirty” Harry Callahan in a grand total of four sequels, from Magnum Force to The Dead Pool. Callahan is arguably Eastwood’s greatest role, making full use of his strengths as an actor and giving him plenty of dramatic material to sink his teeth into, but there are a bunch of other close contenders.

The actor’s decades-long career has been lined with iconic characters. From Sergio Leone’s spaghetti westerns to his own directorial efforts, Eastwood has played a ton of roles that have come close to matching Callahan as a screen icon.

10. Dirty Harry Is The Best: He’s A Quintessential Antihero

Clint Eastwood is best utilized when he’s given less than perfect people to play. His gruff demeanor and icy stare are beautifully matched to antiheroes who do questionable things and try not to look back.

Harry Callahan is a quintessential antihero, breaking away from the police’s codes of conduct if they stand in the way of what he sees as the right course of action.

9. Alternative: Frankie Dunn

Although Million Dollar Baby was marketed as a female version of Rocky, it becomes a much more depressing affair after its midpoint twist in which its protagonist, budding boxer Maggie Fitzgerald, is disabled at the beginning of her promising career.

Clint Eastwood co-stars as Maggie’s trainer Frankie Dunn, who champions her through her first few fights and then has to contend with the heartache of her sudden paralysis.

8. Dirty Harry Is The Best: He’s Eastwood’s Darkest Character

The best acting plumbs the darkest depths of the human soul, from Martin Sheen’s turn as Captain Willard in Apocalypse Now to Al Pacino’s portrayal of the corruption of Michael Corleone in The Godfather trilogy.

Clint Eastwood is one of the world’s greatest actors in terms of playing dark roles. As a cop who will torture suspects without thinking twice, Harry Callahan is easily Eastwood’s darkest role.

7. Alternative: Josey Wales

The title role in The Outlaw Josey Wales is a challenging one, as he’s a farmer whose family is murdered by the Union during the Civil War who then joins a Confederate guerrilla army in pursuit of vengeance.

In addition to directing The Outlaw Josey Wales as a magnificent study of the Civil War, Eastwood starred as one of his most iconic characters.

6. Dirty Harry Is The Best: He’s Morally Complex

Unlike a lot of gun-toting detectives in Hollywood cinema, Harry Callahan isn’t depicted as a clear-cut hero. He’ll bend the law in order to catch a bad guy or he’ll feel justified in killing if he thinks it will prevent more killing.

The audience isn’t expected to be on Harry’s side at every turn, but the moral gray area in which he operates means he’s never anything less than compelling.

5. Alternative: Walt Kowalski

In Gran Torino, Eastwood stars as Walt Kowalski, a Korean War veteran who now lives in a neighborhood filled with Korean gangsters. As he’s caught in a gangland conflict, he confronts his own prejudices and makes the ultimate sacrifice in a harrowing finale.

The actor’s ice-cold glare was perfect for the role of Kowalski. He plays the role as a typical crotchety old neighbor, but with a dark side that’s as clear as day.

4. Dirty Harry Is The Best: He Has Most Of Eastwood’s Quotable Lines

Over the course of an incredible career that spans seven decades and counting, Clint Eastwood has uttered a ton of memorable lines on the big screen that have been quoted by fans ever since.

But the majority of his most beloved quotes belong to Harry Callahan, like “Go ahead, make my day,” “A man’s got to know his limitations,” and “You’ve gotta ask yourself one question: ‘Do I feel lucky?’ Well, do ya, punk?”

3. Alternative: William Munny

Eastwood gave the perfect swansong to the outdated genre that spawned his career with the bleak revisionist western Unforgiven. Years after turning his back on a life of killing to lead a simple farming existence, William Munny is reluctantly recruited for one last gig as an outlaw.

The movie is a grisly tale of redemption as Munny strives to exact brutal vigilante justice, but it also takes every chance to remind viewers that he’s no hero.

2. Dirty Harry Is The Best: A Lot Of Eastwood’s Subsequent Roles Emulated Harry

After the success of Dirty Harry, the title character became Clint Eastwood’s defining role, to the point that many of his subsequent roles were written to emulate Harry’s blunt, unconventional style.

Eastwood had made his name as a cowboy in Italian westerns and playing an iconic detective on the streets of San Francisco ensured him a career in contemporary American thrillers.

1. Alternative: The Man With No Name

Between 1964 and 1966, Clint Eastwood teamed up with Sergio Leone to create three of the greatest westerns ever made. With A Fistful of Dollars, Leone recontextualized Kurosawa’s Yojimbo for the Wild West and pioneered the spaghetti western. With The Good, the Bad, and the Ugly, he perfected the genre.

Across all three movies, Eastwood played the fabled Man with No Name, a gunslinging drifter who chases bounties and plays gangs against each other.

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Clint Eastwood

Why Clint Eastwood Only Acts In Movies He Directs (And When It Started)

Clint Eastwood has largely acted in movies that he was also directing throughout a large portion of his career – so why is this, and when did it start? He will forever be remembered for the Westerns he starred in, however, his directing career reads as a mightily impressive one. Even the films that he has directed but not appeared in, have also gone on to achieve incredible commercial and critical success. His latest western Cry Macho was released last year, and had Clint Eastwood starring, directing, and producing. But why does he only seem interested in appearing in movies that he directs himself?

Clint Eastwood found his way onto TV screens with his breakout role in Rawhide. He then went on to achieve incredible fame and success as ‘the Man with No Name’ in the legendary Dollars Trilogy, directed by none other than Sergio Leone. However, in 1971 he took up dual roles of being both in front and behind the camera in Play Misty for Me, and so marked the beginning of his incredible career in directing. From here on out, the Dirty Harry star was more interested in being the conductor of his own orchestra – to the extent that Eastwood literally even composed music for the soundtracks on many of his films.

Since then, Clint Eastwood never took his foot off the gas when it came to directing and his success in the area is plain to see. Prime examples of this are his four Academy Award wins, two each for Best Picture and Best Director for Unforgiven and Million Dollar Baby respectively, as well as his two Best Actor nominations. Eastwood has never explained why he only acts in movies he directs, but it is clear to see it is a method that works for him – with this likely being the main reason his film efforts have taken this direction. While he had been self-directing for many years previous, the release of White Hunter Black Heart in 1990 marked the beginning of Clint Eastwood acting solely in films he was directing. From this point, he would only appear in front of the lens if he was also the man behind it.

Clint Eastwood had reportedly become frustrated with the atmosphere and pace of some film sets and wanted to create his own environment for making movies. He explained in his book Film Craft: Directing that “sets didn’t have to be nerve-wracking or bell-ringing or booby-trapped as it was with some“. So when Clint Eastwood directed his movies, he encouraged a “comfortable and calm environment on set” and kept the scenes moving. Many actors who have worked with him have said that most shots are done in one or two takes, which is astonishingly efficient – in fact, Eastwood is said to have taken over directing in the 1976 film The Outlaw Josey Wales because he believed it was being directed at too slow a pace.

At 91, it is of no surprise that Clint Eastwood’s movie career is at a point where he has decided that no one is going to tell him what to do besides himself. The exception to this came in 2012, when he starred in Trouble with the Curve – but that was the first project that he had acted in and not directed since his cameo appearance as himself in the 1995 film Casper. What movie Eastwood does next is anyone’s guess. Clint Eastwood has shown he is willing to work with directors in the not-so-distant past, but it’s evident that the actor is clearly someone who likes to work at his own pace – and with such a lengthy history in the industry, it makes sense he uses all his range of abilities to ensure this pace is set.

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Clint Eastwood

Clint Eastwood To Direct & Star In 70s Rodeo Drama

Clint Eastwood sets the 1970s-era drama Cry Macho as his next movie. An iconic Hollywood legend with a career spanning 8 decades, Eastwood continues to work at a rapid pace despite now being 90 years old. Though Eastwood in recent years has largely restricted himself to working behind the camera, the star did step back before the lens in 2018 for The Mule, which went on to gross $174 million at the worldwide box office.

As reported by Deadline, Eastwood is again ready to pull double duty as actor and director for his next project, the Warner Bros. drama Cry Macho. Though the film does not yet have an official greenlight from the studio, and even though COVID restrictions are in place everywhere, Eastwood is said to already be scouting locations. Frequent Eastwood collaborator Nick Schenk penned the script, based on a screenplay by Cry Macho novelist N. Richard Nash, who passed away in 2000. Interestingly, Eastwood’s fellow action icon Arnold Schwarzenegger was originally set to play the lead role in an adaptation of the same book back in 2011.

Set in 1978, Nash’s Cry Macho follows a washed up rodeo star who develops a bond with a young Mexican boy after getting involved in a scheme to take the boy away from his alcoholic mother. Over the course of the story, the boy learns what it means to be a man from his hard-scrabble elder while Eastwood’s character receives a measure of redemption. Warner Bros. is hoping the new film marks a return to form for Eastwood after his last effort Richard Jewell proved to be somewhat of a disappointment, grossing just $43 million worldwide on a budget of $45 million. Indeed, Cry Macho sounds like a solid vehicle for Eastwood, with its neo-Western story involving the unlikely bond between an older man and a youngster in need of some guidance.

Set in 1978, Nash’s Cry Macho follows a washed up rodeo star who develops a bond with a young Mexican boy after getting involved in a scheme to take the boy away from his alcoholic mother. Over the course of the story, the boy learns what it means to be a man from his hard-scrabble elder while Eastwood’s character receives a measure of redemption. Warner Bros. is hoping the new film marks a return to form for Eastwood after his last effort Richard Jewell proved to be somewhat of a disappointment, grossing just $43 million worldwide on a budget of $45 million. Indeed, Cry Macho sounds like a solid vehicle for Eastwood, with its neo-Western story involving the unlikely bond between an older man and a youngster in need of some guidance.

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