Clint Eastwood Regrets His Most Unconventional Western

In 1967, Clint Eastwood's career took off overnight with the U.S. theatrical releases of "A Fistful of Dollars," "For a Few Dollars More" and "The Good, the Bad and the Ugly." This trilogy of newfangled Spaghetti Westerns directed by the brilliant Sergio Leone transformed Eastwood from a TV cowboy (as Rowdy Yates on CBS' "Rawhide") to a gunslinging antihero. The genre was reborn, and Eastwood was suddenly John Wayne for the Baby Boomer generation. He expanded his range and bolstered his popularity the following year by genre-hopping from Western "Hang 'Em High" to cop flick "Coogan's Bluff" to World War II spy thriller "Where Eagles Dare." By the time 1969 rolled around, he could do just about anything — and he did the unexpected.

Though musicals and traditional Westerns were declining in popularity, Paramount thought it could give them both a jolt by mounting a big-screen adaptation of the popular Alan Jay Lerner and Frederick Lowe 1951 musical "Paint Your Wagon." It's a rollicking show set during the California gold rush stuffed with memorable tunes and colorful characters. With veteran musical director Joshua Logan ("South Pacific" and "Camelot") at the helm, it seemed like a safe bet to at least break even commercially; at most, it could turn out to be a box office smash and a major Oscar contender.

Casting would be key, and that's where Logan turned a safe bet into an oddball gamble. Instead of casting musically inclined actors to play the lead roles, he went with the non-singing likes of Clint Eastwood, Jean Seberg, and Lee Marvin. The result wasn't a disaster per se, but Eastwood nevertheless regretted it.

In a 2017 interview with Empire, Eastwood credits perhaps a surfeit of newly earned confidence as the reason he opted to star as the gold-seeking Pardner opposite Lee Marvin's hell-raising Ben Rumson. "I was crazy enough to try anything," said Eastwood. "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."

Technically, it was. Aesthetically, it was not exactly pleasing. While Logan's leads couldn't quite carry a tune (Marvin is much worse), Jean Seberg was dubbed by veteran belter Anita Gordon to keep moviegoers from bleeding out from their ears.

Eastwood could see trouble was coming and tried to quit the production before shooting started, but Lerner and Logan flew to the set of "Where Eagles Dare" to convince him to stay on. Eastwood relented but went on to rue this decision. "Paint Your Wagon" took six months to shoot, an eternity for an efficient actor-director famous for bringing films in ahead of schedule and under budget. Though "Paint Your Wagon" did eventually find an audience, it's still remembered as an odd duck of a movie musical.