Clint Eastwood initially rose to fame playing the young cattle hand Rowdy Yates on Rawhide from 1959 to 1965. Though the young actor broke into TV starring in a western, it was a trilogy of Italian western films that would make him a bonified movie star. Of course, we’re referring to the “Man with No Name” films.

Director Sergio Leone’s A Fistful of Dollars, For a Few Dollars More, and The Good, the Bad, and the Ugly established Eastwood as an icon. However, those films didn’t hit the United States until years after their international release. This meant Clint signed onto several lesser projects while waiting for his A-list status to kick in.

Enter the infamous Paint Your Wagon, a period musical comedy starring Eastwood and that other noted song and dance-man, Lee Marvin.

How the Bizarre Musical Western Led to Clint Eastwood’s Directing Career

Due to production hell, The Good, The Bad, and The Ugly had shot Clint to superstardom by the time shooting began for the musical. However, the actor was unable to break free from his contract, meaning he had to toe the line with the ever-changing production. Paint Your Wagon was based on a Broadway musical from 1951. However, the movie underwent significant changes during production, including the introduction of a love triangle. To make matters worse, the gruff leading men were also made to play up a romantic angle between themselves in addition to leading lady Jean Seberg. Pretty cutting-edge, even for the free-love 60s.

Paint Your Wagon is considered quite a blunder in Eastwood’s career. It holds a dismal 33% on Rotten Tomatoes. The film is so infamous, that it was even parodied on The Simpsons. However, it is a treat to see notorious tough guy Lee Marvin ham it up in such an unusual project.

The script changes and production problems led Clint Eastwood to seek more creative control on future projects. Ultimately, this led the actor to also become a director. Just two years later in 1971, he would helm and star in the thriller Play Misty for Me. Essentially, we owe Eastwood’s prolific, Oscar-winning directing career to the debacle that was Paint Your Wagon.

Many fans point out that Eastwood has far from a fetching voice in Paint Your Wagon. However, the actor-director already proved his singing chops in a Rawhide tie-in album from 1962. Rawhide’s Clint Eastwood Sings Cowboy Favorites showcased that Clint could be a convincing crooner. Of course, Eastwood is an accomplished musician and has scored several films. He even performed his own vocals and music in the 1982 film, Honkytonk Man. Watch him tickle the ivories below.