Clint Eastwood names the most regrettable movie of his career: “The one picture I failed in”
Having conquered Hollywood on two fronts to go down in history as one of its most iconic actors and accomplished directors, Clint Eastwood shouldn’t have too many regrets over how his career panned out.
His famously gruff, grizzled, and no-nonsense personality in front of the camera, behind it, and away from it also means that he’s not one to get misty-eyed, dwell on the past or rue the things he should or could have done. Still, he wouldn’t be human if he didn’t have at least one movie that stuck in his mind as a missed opportunity, even if he was generally happy with his work.
The early 1970s were the single most pivotal period in Eastwood’s professional life and the point where he’d discover if he would sink or swim. He’d become synonymous with the western, with Sergio Leone’s Dollars trilogy turning him into a star and the genre’s new face, but a trio of successful European films wasn’t guaranteed to translate into Hollywood success.
1968’s Hang ‘Em High indicated that the actor’s tried-and-trusted gunslinger archetype translated well to American audiences, before the dismal Paint Your Wagon illustrated that the combination of Eastwood and the western wasn’t enough to polish a steaming cinematic turd.
1971 was undoubtedly the definitive year of his career, and according to Eastwood, he only went two-for-three. That was the year he made his feature-length directorial debut in Play Misty for Me and headlined Dirty Harry, which left The Beguiled on the outside looking in.
Directed by regular collaborator Don Siegel and released seven months before their seminal Dirty Harry, Eastwood went against type in a psychological thriller that the studio struggled to market. As a result of not knowing how to sell it to the general public, the literary adaptation received mixed reviews and flopped at the box office, which left the leading man feeling like he’d let everybody down.
“The one picture I failed in was The Beguiled,” he told Film Comment. “It was good for me personally, critically well-received, but it was very poor for the company that spent the money to produce it.” Eastwood’s biggest issues were with the plot, which he didn’t think was set up to give paying customers what they wanted to see.
“Maybe it couldn’t have been successful because the hero failed,” he pondered. “He tried to do everything through the back door. He wasn’t such a bad person; he was just trying to exist.” It wasn’t his usual type of character, and it wasn’t his usual type of film, leaving Eastwood to believe that he hadn’t done his job properly to bring enough depth and complexity to the role.
In the grand scheme of things, it didn’t really matter career-wise. By the time Play Misty for Me had established his directorial credentials and Dirty Harry had become a cultural phenomenon within the next few months, nobody was even talking about The Beguiled by the end of ’71. Then again, it’s easy to see why Eastwood thought he’d failed when his other two films that year had such a transformative effect on his trajectory, leaving it as the odd one out.
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