Clint Eastwood hates his first and only foray into the musical genre, which was Paint Your Wagon. Released in 1969, Paint Your Wagon was an off-brand project for the actor, who had made a name for himself as a Hollywood “tough guy” and one of its biggest Western stars. The film was one of several movies he’s made over the years that contrasted with his iconic image.
The 1969 musical was one of a handful of movies that Eastwood starred in after The Dollars Trilogy that he made in Italy with critically acclaimed director Sergio Leone. The success he achieved with A Fistful of Dollars, For a Few Dollars More, and The Good, the Bad, and the Ugly, culminated in Eastwood landing quite a few starring roles in big Hollywood movies. Most involved Eastwood playing protagonists that shared qualities made popular by his Man With No Name character. This was certainly the case for films like Hang ‘em High, but it certainly didn’t apply to Paint Your Wagon, a musical Eastwood made with Jean Seberg and fellow Western icon Lee Marvin.
Paint Your Wagon is universally disliked by Eastwood fans and critics alike. Many felt that a singing role just didn’t work for Eastwood (or Marvin). For the most part, this opinion of the film is shared by the actor, whose comments on the subject have made it abundantly how dissatisfied he was with the film. Eastwood signed on to the picture with high expectations for the movie. Unfortunately, rewrites to the script ruined what he originally thought would have been a good film [Empire Online]. Eastwood was incredibly frustrated with the filming process, as the production lasted much longer than planned. Numerous issues slowed down the shoot, causing it to go on for six months.
In the beginning, the Fistful of Dollars star was under the impression that Paint Your Wagon was going to be a musical unlike anything he had ever seen before. Early drafts indicated to him that it would be a dark story that revolved around an interracial romance, which wasn’t that common at the time. This interested Eastwood, but while shooting When Eagles Dare, he found out that the plan for Paint Your Wagon no longer had those elements. He strongly considered backing out but ultimately agreed to see the project through.
When looking at the finished product, it’s easy to why the actor found Paint Your Wagon so disappointing. The actor who played brooding, unbeatable gunslingers like the Man with No Name seemed grossly miscast as a singing cowboy. It created a terrible contrast with the image he had cultivated throughout the 1960s. Plus, the light-hearted tone is so different from the roles Clint Eastwood is typically associated with. There’s no telling what Paint Your Wagon could have been if it had remained the dark, musical Western the studio had sold him on in the first place.