The movies Clint Eastwood called the greatest risks of his career

For a Hollywood icon synonymous with westerns and tough guy roles, Clint Eastwood has always had a career with more variation than critics give him credit for. In fact, he has taken countless risks as both an actor and director over the last 50 years. For instance, he released a western musical at the height of his fame as a gunslinger, made an action movie with an orangutan sidekick, and directed an adaptation of a Broadway musical with a cast filled almost entirely by theatre actors unknown to mainstream Hollywood audiences. He also directed a movie about a terrorist attack on a French train and cast the actual people from the real-life incident in the film. This is not a man who isn’t willing to roll the dice on occasion – but there are three other films Eastwood believes were the greatest risks of his career.

During a 1996 interview with Charlie Rose, Eastwood was asked what he considered the most significant swings he’d taken in his career, and he quickly noted three films. The first was The Beguiled, a 1971 southern gothic psychological thriller directed by Don Siegel. It cast Eastwood as a wounded Union soldier recovering in a Confederate all-girls school during the American Civil War. The themes of the movie centred on sex, revenge, violence, and the consequences of a man having relations with multiple women. Throughout the film, Eastwood’s Corporal John ‘McBee’ McBurney is duplicitous and manipulative but is emasculated by the female characters.

Naturally, this was as far away from Eastwood as a rootin’ tootin’ cowboy as you could get – and audiences didn’t care for it. Universal struggled to know how to market the film, so it put Eastwood on the poster wielding a gun. This suggested an action movie, which couldn’t have been further from the truth. Eastwood was so frustrated with how the studio handled the film that he refused to work with it between 1975 and 2008.

Ultimately, Eastwood tried to play against type in The Beguiled, and it didn’t pay off for him. He felt that audiences and critics didn’t want to see him as a “loser”, musing, “Dustin Hoffman and Al Pacino play losers very well. But my audience likes to be in there vicariously with a winner. That isn’t always popular with critics. My characters have sensitivity and vulnerabilities, but they’re still winners.”

Eastwood also considered his 1982 comedy musical Honkytonk Man a huge risk. He directed and starred in the film, which may have simply been too nice and low-key for its own good. It had the worst opening weekend of any of his films and ended its run as his least successful film at the box office for a decade.

Finally, in 1980, Bronco Billy was a film Eastwood considered a risk but also believed to be his “definitive” movie. Once again, he tried to go the funny route while still staying within the guardrails of a drama. The film told the tale of the struggling owner of a Wild West show, and it was one of Eastwood’s first attempts to make a meta-commentary on his career. In fact, he once said, “It was an old-fashioned theme, probably too old-fashioned since the film didn’t do as well as we hoped. But if, as a film director, I ever wanted to say something, you’ll find it in Bronco Billy.” It’s clear the film, even though it’s been somewhat forgotten in the Eastwood canon, is a hugely important one to the man himself.

In the end, Eastwood has always been willing to try things he’s never attempted before, and that’s hugely admirable. Sometimes, these risks pay off, and sometimes, they don’t – but he’s never let it stop him from taking another swing.

In 2014, he told Daily Actor about his overriding philosophy: “I just never let the old man in. I was always looking for new things to do. I rightfully or wrongly always thought I could do anything.”

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