Actor/Director Spotlight: Clint Eastwood

91 and still kicking, we look at the career of Clint Eastwood as his new movie opens this weekend

One of the most prolific and iconic figures in the history of filmmaking just won’t quit. Clint Eastwood is 91 years old (!), he’s appeared in over 50 films and directed almost 40, and he has a new movie out this weekend called Cry Macho, in theaters and streaming on HBO Max. 

Starting out as a TV Western actor in the 1950s, Eastwood has gone through many career iterations since. He gained international recognition as the Man with No Name in Sergio Leone’s iconic Spaghetti Western trilogy in the 60s. Throughout the 70s and 80s, he began directing some of his own films while also becoming the famous antihero Dirty Harry in five movies. By the 90s, Eastwood had morphed into an award-winning filmmaker and living legend. Known as one-take Clint, he’s been churning out a new movie almost every year for decades now. 

Movie history owes so much to Eastwood, so the least we could do is devote an entire newsletter to the man and the myth. Read on as we break down some of his most legendary roles and films. 

Billy recommends…

A Fistful of Dollars (streaming on Amazon Prime)

The cinema marriage of Clint Eastwood and Sergio Leone is one of the most unique pairings in film history. An Italian director fascinated by the American west brings a now iconic American film legend, Clint Eastwood, into the limelight for the first time. It is just one of the best “inside Hollywood” stories to tell. A non-American in Leone seems to fully understand, or create, the mythos for the western film genre. At age 91 Eastwood is sticking to what has made him famous by directing a modern western, Cry Macho. He is forever linked to the genre. There is no sense in shying away from it now.  

Back in 1964… yes, A Fistful of Dollars was made in 1964… Eastwood was an unknown commodity. The stoic nature that he provides in his breakout performance is what he is known for to this day. Stoicism almost always leaves room for great mystery and Leone purposefully leans into that quality of his lead character. Modern day cinema has plenty of original characters that start off in a similar place, but the enticing nature of that mystery leads greedy Hollywood to show us too much about a character in future projects. Here we get all that same mystery without the explanation and the story is all the better for it.

Our “man with no name” comes in 3 different iterations: A Fistful of Dollars, For a Few Dollars More, and The Good, The Bad, and The Ugly. Each provides more context for the west region and the atmosphere, but no more clarity for where our character comes from. We just want to spend time with this character because of the enticing landscape, inventive filmmaking, and an all time soundtrack from Ennio Morricone.

The stoicism that this character exemplifies is instilled in Eastwood to this day. The man is 91 and is churning out content with no sign of stopping. His films during the new millennium have not been my cup of tea generally, but he is worthy of seeking out to this day. The man clearly likes making things and that is what Do You Like Apples is all about. Embracing the world of film at every turn even when it seems impossible to take it all in. Eastwood is one of the cornerstones of American filmmaking. Don’t let his notoriety fool you, though. Like his breakout character, he is stoic and mysterious. Use this time to try and understand the legacy of Eastwood’s career by watching some of our suggestions.

Drew recommends…

Gran Torino (streaming on HBO Max)

No character has become more identified with late period Clint Eastwood than Walt Kowalski from Gran Torino. With his heart of gold peeking out beneath a “get off my lawn” racist disposition, the character made Eastwood into the grouchy grandpa that everyone not-so-secretly wanted. Gran Torino earned just shy of $270 million worldwide at the box office in 2008, the biggest hit of Eastwood’s long and storied directorial career until 2014’s American Sniper. While it may not be Eastwood’s artistic height, Gran Torino proved he could keep delivering characters that reexamined his own iconic persona well into his old age. 

I’m pretty confident Eastwood is the only one that could’ve convincingly pulled off the Walt character. Here’s a bigoted old widower that sits on his porch smoking and drinking while staring daggers and muttering slurs at his Asian neighbors, his shotgun at the ready if anyone dares step on his property. Walt is a Korean War vet and retired Detroit-area auto worker that can’t stand the multicultural shift in his community. Because of the history we have with Eastwood as a no-nonsense movie hero, only Clint could realistically play Walt the old racist and still make a sympathetic turn toward redemption of some kind. 

It’s very easy to imagine Gran Torino’s Walt as geriatric Dirty Harry or any of the stoic action heroes of Eastwood’s younger days, mostly because his acting style -- growling his lines through a squinting grimace -- hasn’t changed all that much. What makes this such a fascinating film for his career is how it complicates our view of those cinematic icons. Walt’s flawed worldview is front and center as he alienates himself from his community and his own family, while only finding purpose when he reluctantly forms a bond with his teenage Hmong neighbor, Thao. With a surprisingly humorous tone, Gran Torino asks us to reevaluate the righteous and invincible figures of Eastwood’s past. If you end up as a bitter and isolated old man, maybe you need to learn how to accept those different from you. 

Of course, we still know who will wind up the hero of Gran Torino. Your sympathy may vary for a character that uses insults and slurs with every other word, but I respect that the movie remains true to Walt to the very end. Even if the writing gets a little overwrought in the second half, Gran Torino doesn’t lean on any corny grand realizations. Instead, Walt’s antipathy fades just enough for him to dispense Clint Eastwood vengeance of a different kind than we had become accustomed to. 


Unforgiven (streaming on HBO Max)

*This is a re-post from an April 2021 newsletter

Right before the thunderous climactic stretch of Clint Eastwood’s masterpiece Unforgiven, a young hired killer named the Schofield Kid tells Eastwood’s Will Munny that the men they just killed “had it comin’.” As Munny looks off into the distance with that famous Clint grimace, he makes a corrective: “We all have it comin’, Kid.” Right there in that exchange is the crux of the 1992 Best Picture winner Unforgiven, the Western to end all Westerns. 

After a long and fruitful career as one of the two iconic Western figures (John Wayne is the other), Eastwood hung up his spurs on the genre with Unforgiven, claiming he had said all he wanted to say. His timeless film successfully deconstructed both the traditional Western and the whole Eastwood cinematic persona…

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  • Guillermo del Toro is back on December 17 with Nightmare Alley, another fantasy-horror movie from the Mexican filmmaker. The cast on this one is truly one of the best of the year with Bradley Cooper, Cate Blanchett, Willem Dafoe, Toni Collette, Rooney Mara, and more all starring. Check out the trailer here

  • Christopher Nolan is preparing his new film, which is about one of the fathers of the atom bomb, J. Robert Oppenheimer. After spending most of his career with Warner Bros, Nolan has found a new studio home at Universal. The Hollywood Reporter went in depth on the deal Nolan struck for his new project

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