Clint Eastwood Reveals His Least and Most Favorite Roles

Cry Macho helmer Clint Eastwood has long cultivated a tough guy reputation in Hollywood, and this reputation was already established in 1969 when the actor decided to star in a little musical called Paint Your Wagon. Now the actor has opened up about his short stint as a musical star, and why it was one of his least favorite roles.

Eastwood, an American actor, director, and producer active in the entertainment industry since the 1950s, has long been regarded as a stalwart of the Western genre. As an actor, Eastwood got his big break in 1959 on the Western TV series Rawhide and then made a name for himself as the star of “Spaghetti Westerns” like Sergio Leone’s Dollars Trilogy, 1966’s The Good, the Bad, and the Ugly, and 1968’s Hang ‘Em High. Despite being considered a one-note actor early in his career, today, he is regarded as one of the greatest actors in film history, having received numerous awards and accolades throughout his career.

Although Eastwood is known for his stoic, tough-guy persona, signature squint, and gravelly voice, early in his career, he dabbled in music, developing as a boogie-woogie pianist and producing an album titled “Cowboy Favorites,” released on the Cameo label. With his musical past, perhaps it should come as no surprise that Eastwood also tried two-stepping and singing in the Western-themed musical, Paint Your Wagon.

Directed by Joshua Logan and co-starring Jean Seberg and Lee Marvin, Paint Your Wagon was based on the Broadway musical of the same name and cast Eastwood as Pardner, a hopeless romantic and the survivor of a wagon crash who discovers gold at the funeral of his brother. Although the film received mixed reviews when it debuted, including criticism of Eastwood’s singing, it is now a cult classic. But just because the film was popular with viewers that doesn’t mean that Eastwood enjoyed making it.

“I’ve always been interested in music, my father was a singer, and I had some knowledge of it,” Eastwood told Empire Magazine about his decision to take the role, per Far Out Magazine. “Although what I was doing in that picture was not singing.”

The actor continued, saying that his time on set “was not as pleasant an experience as” he was used to.

Related: Clint Eastwood’s 10 Most Iconic Movie Lines

Clint Eastwood’s Favorite Roles

Warner Bros.

While Eastwood has not specifically stated which of his films is his favorite, he has expressed admiration for a few of his roles. For example, in the past, he has mentioned that he enjoyed playing the character of The Man with No Name in the Dollars Trilogy.

Eastwood has also spoken highly of Unforgiven, which he directed and starred in. Speaking about the film in 1992, he told The Los Angeles Times, “I would never make a Western, just to make a Western. It has to be the story,” before going on to describe the film as one of the more personal projects he had worked on at that time.

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