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Clint Eastwood did not believe that he had many acting roles left to do at his age. However, Eastwood had already made a backup plan if he or the viewers had enough of his acting. His main intention for stepping into the director’s shoes in his 1971 filmPlay Misty for Mewas to stay behind the camera even after retiring from acting. It came as a blessing since Eastwood won his first Oscar as a director for his 1992 filmUnforgiven.

In 2004, he won his second Oscar, again as a director, forMillion Dollar Baby. Moreover, he has directed five actors in Oscar-winning performances. Throughout these years, Eastwood also took up some acting roles, like in his 2004 directorial venture, despite his insecurities about acting.
Clint Eastwood’s Acting Insecurities Turned Him Into An Oscar-winning Director
Clint Eastwoodadapted the bookRope Burns: Stories from the Cornerinto the filmMillion Dollar Babyin 2004 and decided to play the role of trainer Frankie Dunn himself. Eastwood found the underappreciated boxing trainer to be interesting and believed thathe could pull it off like any other actor. When asked whether he still liked to act in a 2005 interview with Film Comment, Eastwood had a rather interesting answer.
“He is the one who my friends talk about”: Matt Damon Had a Life-Changing Experience With Clint Eastwood He Believes That Made Him a Better Actor
He admitted that he loved to act but had often threatened to quit due to his old age at the time. He believed that he couldn’t do a lot of great roles at that age. He went on to share that his directing career was a backup plan in case he had to stop his acting career at some point. He believed that he could still remain a part of films as a director. Eastwood shared withFilm Comment:
You know, I do. I’ve threatened to quit, but maybe that’s a defense mechanism, because there aren’t enough good roles at my age. That’s probably true, and if it is, I’ll stay behind the camera. The reason I started directing 37 years ago was I thought some day I or the audience would probably look at the screen and say, ‘That’s enough of that.’

He further went on to share that he particularly enjoyed directing his filmMystic River, which came beforeHilary Swank‘s boxing drama. In the 2003 film, Eastwood solely worked as a director, and he had a great time observing other actors conquering difficult scenes during filming. He shared:
I had a great experience directing the last film [Mystic River] without being in it. I’m always amazed looking at other actors when they’re conquering the difficulties of different sequences. But this one, I thought Frankie Dunn is interesting, and I’ll be able to do it as well as the next guy.

Million Dollar Babywon four major awards out of its seven nominations at the 77th Academy Awards. TheDirty Harryactor was recognized with the Best Director Oscar, and his film received the Best Picture Oscar. Swank andMorgan Freemanwere also the recipients that year in acting categories.
Clint Eastwood’s First Oscar-Winning Film Was a Mythbreaking Western
Clint Eastwood’s first Oscar win came as a director, and it also came for his last Western movie,Unforgiven. He decided to give up on the genre since he didn’t want to tell the same old stories again. However, he went out with a bang sincehe deconstructed the genreitself with the 1992 film.
“He wanted to sit on the porch and smoke his pipe”: Clint Eastwood’s Comment About His Favorite Movie Villain Should Put Thanos on Oscar Winner’s List
Many people considered his film as anti-Western initially since it destroyed many of the genre’s long-standing myths. He once said that the film wasn’t“anti-Western”but rather a“mythbreaking Western”(via Far Out Magazine). He toldEmpirethatUnforgivenwas the“perfect last Western”for him, as he shared:
I felt like that was the genre I became known in, it had been so good to me, and that this would be the perfect last western for me.

The film broke the concept of a black-and-white hero with William Munny’s dark, ugly backstory, making him a grey-shaded character.Gene Hackman‘s cruel character broke the good guy image of the Town Sheriff in Westerns. S*x workers were shown in a more positive light, and the film showed a cowboy who vows to never take another life after his first kill.
Million Dollar BabyandUnforgivenare now available for rent on AppleTV+.
Hashim Asraff
Senior Writer
Articles Published :3019
Hashim Asraff is a Senior Entertainment Writer at FandomWire, with over 2,800 articles published on celebrity culture, comic book movies, and major TV franchises. With a background in Sociology and a keen interest in pop culture, Hashim brings a unique lens to breaking news stories, character deep-dives, film rankings, and fan-driven perspectives.His coverage often includes the MCU, DCU, hit network shows, and celebrity profiles, giving readers a rich blend of entertainment and analysis. A longtime fan of crime and investigative series, Hashim has watched thousands of episodes of NCIS, Criminal Minds, Law & Order: SVU, Bones, Blue Bloods, and The RookieA passionate storyteller and wordsmith, Hashim has also worked as a ghostwriter and managed multiple social media handles. He brought his writing expertise to FandomWire to also pursue his lifelong love for cinema and television.
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Clint Eastwood
