Relative to the number of professionals to have plied their trade in the industry since the advent of the moving image, the names to become legends are infinitesimally small. And yet, Clint Eastwood has managed to do it twice over.
In front of the camera, he’s one of the most iconic figures in Hollywood history, a generation-spanning legend responsible for a number of timeless characters and lines of dialogue that became woven into the fabric of pop culture, with a persona that’s inspired peers, colleagues, and contemporaries covering decades and multiple genres.
Behind it, he’s a four-time Academy Award-winning filmmaker who gained renown as one of the most efficient and accomplished auteurs of the last 50 years. Eastwood never makes waves behind the scenes, never butts heads with the studio, never goes over his allotted budget, and doesn’t waste so much as a second take unless he really has to.
With that in mind, trying to settle on the most definitive entries in Eastwood’s filmography is an arduous task because there are so damned many of them. From 1955’s B-tier schlocker Revenge of the Creature to 2024’s Juror No 2, his 40th feature as a director, there’s no shortage of candidates to choose from.
However, there is a trio that stands head and shoulders above the rest, albeit for very different reasons. Any career with designs on longevity needs to ride the incoming waves, adapt, and evolve to stay fresh and relevant, something Eastwood has managed with aplomb.
Most people in their 90s would take it easy, put their feet up, and luxuriate in the fruits of their labours. Eastwood isn’t most people, of course, which is why he’s still putting his nose to the grindstone and keeping himself busy. Obviously, he’s much closer to the end of his career than he is to the beginning, but his run wouldn’t be anywhere near as legendary if it weren’t for the following three features.
A Fistful of Dollars (Sergio Leone, 1964)
It might be stating the obvious to point towards the first instalment in the Sergio Leone trilogy as the genesis point of Eastwood as a movie star, but that doesn’t make it any less true.
Everything audiences have come to know, love, appreciate, and regularly impersonate about the actor’s signature spate of onscreen tics, traits, and characteristics were first glimpsed in A Fistful of Dollars, making the ‘Man With No Name’ one of cinema’s most enigmatic icons in the process.
It was only the fifth time Eastwood had ever been credited in a feature, and it was the first major leading role of his motion picture career. As far as making an impression right out of the gate goes, exuding star power, screen presence, and quiet charisma in an influential western that breathed new life into an entire genre is one of the most impressive ways anybody has ever gone about it.
Every Which Way but Loose (James Fargo, 1978)
Yep, it’s the orangutan movie. Most people wouldn’t look at the frivolous comedy caper as being one of Eastwood’s most definitive films, but dig a little deeper, and it’s much more deserving of that distinction than anything else he made post-Dollars. And yes, that includes Dirty Harry.
Between The Good, the Bad and the Ugly and Every Which Way but Loose, Eastwood solidified his stardom and underlined his action hero credentials in films like Hang ‘Em High, Coogan’s Bluff, Where Eagles Dare, Thunderbolt and Lightfoot, The Eiger Sanction, and the first three entries in the Harry Callahan franchise.
Meanwhile, his nascent directing career took off after his 1971 debut, Play Misty for Me, which was followed by another five features, including The Outlaw Josey Wales. Eastwood was a made man on two fronts, but sharing the screen with a simian was the epitome of his ironclad self-belief on a level that nothing he made during that period could match.
The star’s representatives told him it was a bad idea and actively tried to dissuade him from signing on. Eastwood, ever the savvy operator, knew that if Every Which Way but Loose turned out the way he imagined, it would add new shades to his screen persona and inform audiences that he wasn’t too shabby at the whole comedy thing.
What was the end result? It was the best box office opening weekend of his entire career, and by the time the dust had settled, it was the highest-grossing film he’d ever starred in. Not only that, but Only Which Way but Loose would remain his top-earning effort at the global box office for 14 years, and adjusted for inflation, it’s never been topped as the highest-grossing starring vehicle in his filmography.
Unforgiven (Clint Eastwood, 1992)
It simply couldn’t be anything else, with Unforgiven regarded as Eastwood’s magnum opus on either side of the camera and a movie that serves an important function well beyond the confines of the silver screen.
His crowning achievement as a filmmaker, the long-gestating passion project won the leading man and director his first two Oscars for ‘Best Picture’ and ‘Best Director’, and was immediately welcomed as one of the greatest westerns ever made.
Doubling up as his swansong to the genre that made him who he is and carrying every ounce of that baggage into the story, exclamation points rarely come as definitive as Unforgiven. It was the culmination of everything Eastwood had become over the preceding 30 years, drawing a line under his association with the western in seminal style.