All children look up to their parents, and, for at least a period of their lives, most dream of following in their footsteps with their career. Though he’s known today as a grizzled western movie star, as a child, Clint Eastwood was just a boy who wanted to be like his father.

Clint Eastwood’s father wasn’t an actor but a singer, which inspired Eastwood to dip his toes in the world of musicals for a production of Paint Your Wagon. In an interview with Empire, Clint Eastwood described the experience.

“I was crazy enough to try anything,” Eastwood said of attempt at singing. “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.”

In addition to his frustration with his lack of singing ability, Paint Your Wagon wasn’t a smooth production. The finished product wasn’t at all what Eastwood was told it would be, which left an even worse taste in his mouth.

According to Clint Eastwood, Paint Your Wagon was “much lighter” and “didn’t have the dynamics that the original script did”. Though he gave it an honest effort, his single musical effort was “not a pleasant experience” for Eastwood, and he decided right then and there that he would leave the singing to his father.

Luckily, it wasn’t long before fate intervened. Just two years later, a little-known film entitled Dirty Harry fell into Clint Eastwood’s lap, and the rest is history.

Clint Eastwood Discusses the ‘Worst’ Movie He Ever Made

There’s no question that Clint Eastwood has had an incredibly successful career in movies. Even those who aren’t fans of westerns can’t deny that seldom few actors can say that they’ve been in Hollywood for 70 years.

That said, no one can have a 70-year career without at least one flop. And for Clint Eastwood, that project came in the form of Ambush at Cimarron Pass, one of the first Western movies he ever did. It’s safe to say that Eastwood despises that film, as he once called it “the worst film ever made.”

In an interview with The Hollywood Reporter, Clint Eastwood explained that he hated the film so much it almost put a premature end to his acting career. “The film was made in eight days. And I saw it. I went to see it, it was playing a second feature in North Hollywood. I want to see it and I saw that film and I said, ‘I’m through. I’ve got to go back to school. I’ve got to do something else, I’ve got to get a job of other sorts.”

Thankfully for Eastwood fans, he didn’t go through with this decision and fate intervened once again. “Finally I accidentally ran into somebody out at CBS on Beverly Boulevard,” Eastwood recalled. “And they were doing a Western called Rawhide. And they cast me as one of the leads.”