A career as long and successful as the one enjoyed by Clint Eastwood isn’t going to come laden with many regrets, but the iconic actor and filmmaker vividly recalls one production as being so nightmarish that he considered walking away before cameras had even finished rolling.
Obviously, he didn’t and persevered until the final day of principal photography, only for his performance to be savaged, the response from critics and audiences to be generously described as anaemic at best, and the end result to endure more than half a century on as one of Eastwood’s most excruciating and misguided efforts on either side of the camera.
Eastwood has played some of the most indelible characters in cinema history, won four Academy Awards for his efforts as a director and amassed a legion of fans spanning generations, while history is destined to remember him as one of the silver screen’s greatest-ever legends. However, despite his best efforts to convince people otherwise, he was never cut out to be a singer.
He released an album of cowboy ditties at the peak of his Rawhide days, crooned his way through several songs that appeared in his movies, and clearly envisioned himself as a triple threat of actor, filmmaker, and musician, but Paint Your Wagon is evidence enough that he didn’t have the chops, or the pipes, to pull it off.
“I was crazy enough to try anything,” he told Empire of his disastrous foray into a full-blown musical. “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.”
At least he’s honest enough to admit that he was crap because he was. Paint Your Wagon was a massive misfire, but it also suffered through its fair share of behind-the-scenes difficulties. The script went through so many rewrites and revisions that it was barely recognisable to the one that had enticed Eastwood in the first place, which made his patience wear awfully thin.
The delays dragged on for so long that the star had the time to shoot Where Eagles Dare during his downtime, and he was ready to wash his hands of Paint Your Wagon completely until scribe Alan Jay Lerner and director Joshua Logan “flew over and talked me back.” The war thriller was shot in England, Austria, and Germany, so the fact two of the key creatives crossed continents to twist Eastwood’s arm indicates just how close he was to abandoning the ship.
Even in its finished form, Paint Your Wagon “didn’t have the dynamics that the original script did,” and shooting going massively over budget and behind schedule struck a nerve for a professional like Eastwood, who acknowledged that the film “was not as pleasant an experience as I was used to.”
There were 17 months between the first day of shooting on Paint Your Wagon and its premiere. Between those two points, Eastwood was ready to quit before being talked down from the ledge, only to power through a script he didn’t like for the sole purpose of the picture turning a minuscule profit and its lasting legacy being the mockery he faced for his terrible singing voice.