Clint Eastwood names the best movies of his career: “Sometimes you trip over things and it comes out good”
Clint Eastwood’s career is a tapestry of varied successes. Beginning in the 1950s with the television series Rawhide, he quickly transitioned into movie stardom through Sergio Leone’s Dollars Trilogy. While cementing his status as one of Hollywood’s most bankable stars, Eastwood began directing films, starting with 1971’s Play Misty for Me. As it turned out, he was exceptionally talented behind the camera, going on to craft a directorial career even more illustrious than his acting one. Somewhere along the way, as one does, he also became the mayor of Carmel, California.
In total, Eastwood has won four Academy Awards for ‘Best Director’ and ‘Best Picture’ and earned seven further nominations across two decades. At 94, he’s released yet another critically acclaimed film, Juror #2, which may earn him several more accolades.
After such an illustrious career, it would surely be difficult to pick favourites, but Eastwood did just that in a 2021 interview with Parade. When asked whether there were any roles he felt proudest of, the filmmaker said, “I think it changes – for the better. I’m thinking of Unforgiven. I had done a lot of westerns, but this had a different story element to it. The Outlaw Josey Wales was an interesting story. And Million Dollar Baby. Sometimes you just trip over things, and it comes out good – or bad.”
Eastwood plays a similar character in all three films, even though one of them (Million Dollar Baby) is not a western. He’s in his comfort zone as a loner with a violent streak who maintains his own code of ethics independent of the society around him, but he imbued each role with subtle differences.
Released in 1976, The Outlaw Josey Wales was one of Eastwood’s earliest forays into directing. In it, he plays a former Civil War soldier-turned-outlaw seeking to avenge the brutal murder of his wife and son. It was a box office smash when it was released and became an instant western classic.
1992’s Unforgiven was seen as a revival of the western genre. Starring Eastwood as a retired gunslinger who returns for one last gig, it earned the director his first two Oscars – ‘Best Director’ and ‘Best Picture’ – and a nomination for ‘Best Actor’.
Million Dollar Baby was a departure for the western icon. Hilary Swank plays an amateur boxer trying to become a professional, and Eastwood plays her reluctant trainer, who becomes a father figure. It’s a more emotional role than Eastwood’s previous work, and earned him yet another nomination for ‘Best Actor’ and wins for ‘Best Picture’ and ‘Best Director’.
It’s no coincidence that all of these films were directed by Eastwood himself, and while it’s not surprising that he chose them given their calibre and near-universal acclaim, it’s worth pausing to acknowledge how rare it is for actors to successfully direct themselves as actors. Kevin Costner, Bradley Cooper, and George Clooney have all done it, but it rarely yields their best performances.
Eastwood is an outlier for consistently directing and acting in films that became commercial successes, and it’s safe to say that most critics would agree that the movies he singled out are indeed some of his best work both as a director and as an actor.
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