Clint Eastwood called this 1950s Western the worst film of all time

In 2025, Clint Eastwood will officially celebrate his 70th year in the film industry. That’s only five years less than the average life expectancy of American men, so you could definitely call this a great success, even if he’s only played villains and bartenders since the Eisenhower administration. Of course, Eastwood did a little more. Working with filmmakers Sergio Leone and Don Siegel, Eastwood played an important role in reconfiguring the western/crime genre. He has also won the Oscar for Best Picture and Best Director twice (for Unforgiven and Million Dollar Baby) and, at age 94, will release his latest directorial effort, Juror #2, this November.

Eastwood has been so successful for so long that it’s hard to believe he ever really struggled. But 94 years is a hell of a long time, and this cinematic icon didn’t achieve movie stardom until he was 30. Before that, he starred in a number of unforgettable films and seemed to be on his way to a typical future as a television star.

Eastwood believed he was capable of more, but even he began to have doubts when he caught a glimpse of one of his first significant film performances in a B-Western that he considered an absolute stinker.

In a 2015 interview with The Hollywood Reporter, Eastwood recalled struggling as a contract player at Universal, which led to him landing the third role in a widescreen Western from 20th Century Fox that was like an episode of “F Troop” plays out without any intentional laughs. As Eastwood told THR, it almost put him out of business:

“[F]Finally one day I started getting a few roles and then I did a little film at Fox called Ambush at Cimarron Pass. It was probably the worst movie ever made […] But I had the second lead and an actor named Scott Brady was the lead. And the film was shot in eight days. So it really was el speedo grande. And I saw it. I saw it, it was playing as a second feature in North Hollywood. I watched the movie and said I was done. I have to go back to school. I have to do something else, I have to find another job.

Eastwood wasn’t finished yet. CBS liked his boys’ approach to western acting and cast him as aspiring cowboy Rowdy Yates in the hit TV western “Rawhide.” However, Eastwood quickly became tired of episodic television, which led him, while he was taking a break from series in 1964, to take the risk of filming a violent western in Spain at the time with the hardly proven Italian director Sergio Leone. The film was called A Fistful of Dollars, and at this point Eastwood’s walk turned into a veritable sprint toward international fame.

Ambush at Cimarron Pass is currently available to stream for free on YouTube, but the paint-by-numbers flick is only for Eastwood completists. Seriously, you should watch Pink Cadillac or The Rookie instead.