Before he was one of the most bankable stars in Hollywood, Clint Eastwood was the star of the sixth-longest-running classic TV Western. From 1959 to 1965, Eastwood starred as Rowdy Yates, the young and sometimes rash cattle hand on Rawhide. During those years, Eastwood established himself as a Western actor, so Western roles were all that was available to him when the show ended. Clint made a name for himself on American TV, but three Italian movies catapulted him to international fame.

Sergio Leone's Dollars trilogy made a movie star out of the guy on Rawhide. A Fistful of Dollars, For a Few Dollars More, and The Good, the Bad, and the Ugly propelled Eastwood to new levels of fame. But the praise didn't come right away. While the first of those movies was released internationally in 1964, it didn't show up on American movie screens for several years later. In the interim, Eastwood starred in several movies and signed on to several more. Some of them were successes, like Hang 'Em High and Coogan's Bluff, but not all of his film roles were smash hits. 

By the time The Good, The Bad, and The Ugly made Clint Eastwood a superstar in America, he'd already signed a contract to appear in Paint Your Wagon. Production delays meant that by the time he was on set, Clint Eastwood was in a very different place in his career than he was when he originally agreed to be in the movie. Unfortunately for him, he was unable to wriggle out of the rapidly changing production and was held to his obligations.

Paint Your Wagon was positioned as an adaptation of the 1951 Broadway musical of the same name. However, by the time the movie was in production, the story was very different from the source material. While the story always took place during the California gold rush, the movie injected the tale with a nontraditional love triangle that then-contemporary audiences just weren't ready for. While the object of Eastwood and co-star Lee Marvin's affection was Jean Seberg, the production purposefully added some palpable romantic tension between the two male leads. 

Eastwood was frustrated with the delays and the changes to the story, and the difficulties ultimately led him into directing. Clint Eastwood never again appeared in a production that he didn't control, at least somewhat. And while he always had a tough-guy Hollywood persona, Eastwood as the paragon of hyper-masculinity is a direct reaction to the ways he felt betrayed by Paint Your Wagon.