The one movie Clint Eastwood hated making

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Tue 20 May 2025 17:36, UK

There are countless characters in the long and storied history of Hollywood that fall by the wayside quickly. To become a household name and have that name be remembered for decades, you need to have a sincere and serious cultural impact. Very few actors in the history of cinema can compare to the sheer cultural might of Clint Eastwood, with only a few American stars able to rub shoulders with the western icon, including John Wayne, Marlon Brando and James Dean.

One of the few actors to successfully transition into being a director, Eastwood never won an Oscar for any of his performances but has claimed four Academy Awards for his directing over the years. It is an impressive resume, no matter which way you look at it.  

As one of America’s greatest actors, it’s no surprise that he has featured in some of Hollywood’s very best movies, including Sergio Leone’s seminal Dollars trilogy and Don Siegel’s Dirty Harry. But, just like every actor, not every single one of his movies was perfect, and, in 1969, he made the surprising decision to feature in a musical, namely Joshua Logan’s Paint Your Wagon. 

Based on the Broadway show of the name, the musical tells the story of the survivor of a wagon crash who discovers gold before engaging in a love triangle where he and another man are vying for the love of a woman, Paint Your Wagon is never talked about for a reason.

Criticised by movie fans and critics alike, one of the most highly probed aspects of the film was Eastwood’s dodgy vocal performance. Pitching Eastwood, one of the toughest guys in Hollywood as a singing minstrel was never likely to go down particularly well, but even Eastwood wasn’t a fan of the performance, especially when he had to watch himself back.

“I was crazy enough to try anything,” the actor later admitted when talking about taking on the role so far out of his comfort zone. Eastwood continued: “I’ve always been interested in music, my father was a singer, and I had some knowledge of it. Although what I was doing in that picture was not singing”.

The actor had thought he was signing up for a gritty musical, having read the script, which he liked very much. Yet, further down the line, the screenplay became targeted at a much more general audience, with Eastwood admitting that the script got “much lighter, it just didn’t have the dynamics that the original script did. And that was another long shoot”.

Eastwood later admitted, “That was not as pleasant an experience as I was used to,” in relation to his role in the misguided musical, with the actor listing it alongside some of his least favourite movies of his entire career. Considering the massive number of movies he has made, finding itself near the bottom of the pile is tough, though not unexpected.

Paint Your Wagon certainly ranks beside Ambush at Cimarron Pass, a film that the actor calls, “probably the worst film ever made” before saying in caveat, “But I had the second lead in it, and an actor named Scott Brady was the lead. And the film was made in eight days. So it was really el speedo grande”.

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