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.
As one of America’s greatest actors, there’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.
“I was crazy enough to try anything,” the actor later admitted, “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.
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”.

Clint Eastwood has been known around the world as a veteran director beyond all means. Eastwood, however, started his journey as an actor portraying several iconic and notable roles over the years.
Starring in Sergio Leone’s The Dollars Trilogy, Clint Eastwood starred in a genre of movies called Western spaghetti. Portraying the role of The Man with No Name, Eastwood’s dedication to the role is both commendable and a bit disgusting as he reportedly never washed his character’s cape over the course of three years!

Clint Eastwood in a still from The Mule
Clint Eastwood Wore An Unwashed Serape For Three Years!
Back in 1964, Italian director Sergio Leone released the iconic film A Fistful of Dollars. Portraying the story of an unknown riding into town with two opposing factions, the movie was essentially a cowboy movie with plenty of action scenes for people to enjoy.
In the movie, Clint Eastwood portrayed the role of The Man with No Name. Wearing a serape around his neck and carrying pistols in his holster, Eastwood’s character became notoriously famous from the movie. A year later, Leone released For a Few Dollars More, a sequel to the 1964 film, and Clint Eastwood reprised his role of The Man with No Name.
Finally, in 1966, Sergio Leone released The Good, the Bad and the Ugly, thus completing The Dollars Trilogy. As per a report by Outsider.com, Eastwood never washed his iconic cape throughout the shooting of The Dollars Trilogy. Alleging that the cape was a memorabilia of how far the character had come throughout these movies, Eastwood wore the same cape for three years without washing it once!
Sergio Leone Talked About Working With Clint Eastwood
Although it was Leone’s movies that made Eastwood famous in Hollywood, the director has had some complaints with the veteran actor. Comparing him to Robert de Niro, Sergio Leone revealed in an interview with American Film that Eastwood was like a block of marble!
“Robert De Niro throws him­self into this or that role, putting on a personality the way someone else might put on his coat, naturally and with ele­gance, while Clint Eastwood throws himself into a suit of armor and lowers the visor with a rusty clang.”
He further continued,
“[Clint] East­wood moves like a sleepwalker between explosions and hails of bullets, and he is always the same — a block of marble. Bobby [Robert De Niro], first of all, is an actor. Clint, first of all, is a star. Bobby suffers, Clint yawns.”
Despite whatever the director and Clint Eastwood had between them, the two went their separate ways at the end of The Dollars Trilogy. Eastwood went on to become an iconic actor with his portrayal of action characters and then later became a veteran director with a unique take on movies.

Some stars of Hollywood cinema are indelibly linked to American culture, with the likes of John Wayne, James Stewart, Steven Spielberg and Tom Hanks having made some of the medium’s most patriotic flicks. The actor and director Clint Eastwood is very similar, taking the reins of the western genre from Wayne in the late 20th century, thanks to such hits as The Good, The Bad and the Ugly and The Outlaw Josey Wales.
Rising to popularity in the early 1960s, largely thanks to his role in the TV series Rawhide, where he starred with Eric Fleming, Eastwood later found success on the silver screen, taking the lead role in Sergio Leone’s ‘Dollars’ spaghetti western trilogy, where he played the iconic and mysterious ‘Man With No Name’. By the end of the decade, he was well and truly an established star of contemporary Hollywood.
In the 21st century, with four Academy Awards and 11 nominations under his belt, Eastwood is considered a veteran of the industry who was born in a different time in Hollywood when the studio system era was slowly coming to an end. Much has indeed changed since the time the actor rose to fame, with the movie industry now far more complex due to the rise of streaming, whilst social values have also changed, thankfully becoming far more tactful and accepting of other races and sexual identities.
Yet, speaking in an interview with Esquire back in 2016, it doesn’t appear that Eastwood considers these changes particularly positive.
“Everybody’s getting tired of political correctness, kissing up,” the actor stated in response to how his hardy characters remain relevant in society.
Continuing, he added: “That’s the kiss-ass generation we’re in right now. We’re really in a pussy generation. Everybody’s walking on eggshells. We see people accusing people of being racist and all kinds of stuff. When I grew up, those things weren’t called racist”.
Clearly, a little upset that ‘things aren’t like they used to’, despite the clear social progress of contemporary life, Eastwood goes on to further define his thoughts on the “pussy generation”, exclaiming: “All these people that say, ‘Oh, you can’t do that, and you can’t do this, and you can’t say that.’ I guess it’s just the times”.
Naturally, this conversation led to the subject of Donald Trump, who was, at the time, about to win the 2016 Presidential Election. “What Trump is onto is he’s just saying what’s on his mind. And sometimes it’s not so good. And sometimes it’s…I mean, I can understand where he’s coming from, but I don’t always agree with it,” the actor says of the former President before adding that he doesn’t endorse him.
Take a look at the trailer for Gran Torino, starring Eastwood, a film that deals with political correctness, generational changes and modern-day racism, below.