Looking back on Clint Eastwood's legendary career in Hollywood, there are multiple noteworthy moments that have turned him into the filmmaker he is today. He changed the trajectory of his career by agreeing to star in A Fistful of Dollars for a then-unknown director named Sergio Leone. He's won four Oscars between Unforgiven and Million Dollar Baby. Heck, he's one of the most successful western stars in history. But let's not forget about the time 50 years ago when he tried to sing. That's right...I'm talking about the western-themed musical that was one of the biggest flops of his career back in 1969 -- Paint Your Wagon. We're talking a musical with choreography and everything...starring Clint Eastwood.
It was no doubt a shock to everyone involved that the movie performed so poorly considering the amount of talent involved in bringing it to life. Eastwood was fresh off the Dollars Trilogy and reaching movie star status. Lee Marvin had found success through the 50s and 60s for films like The Killers and The Dirty Dozen. The film was based on a Broadway musical from the team Lerner and Loewe (Alan Jay Lerner and Frederick Loewe), known for hits like My Fair Lady and Brigadoon. Joshua Logan signed on to direct the film, known for winning a Pulitzer Prize for South Pacific and Oscar-winning screenwriter Paddy Chayefsky signed on to adapt the film version. It's an impressive list of talent but somehow it still just didn't land.
Read More: There's a Reason John Wayne and Clint Eastwood Never Worked Together
The storyline takes place during the California Gold Rush with Jean Seberg co-starring as Elizabeth, the love interest for both Eastwood's character "Pardner" and Marvin's character Prospector Ben Rumson. Ben first discovers Pardner after he narrowly survives a wagon crash in the mountains of California. While Ben buries the man's brother who perished in the crash, he discovers gold and builds up "No Name City" with Pardner as his partner. While the story works in the grand scheme of westerns, it didn't necessarily work as a musical despite having some incredible songs, some coming from Oscar winner Andre Previn. Harve Presnell (Rotten Luck Willie), Ray Walston ("Mad Jack" Duncan), Tom Ligon (Horton Fenty), and Alan Dexter (The Parson) round out the impressive cast as a unique set of characters in town.
Both Marvin and Eastwood do their own singing in the film. Eastwood's songs include "I Still See Elisa," "I Talk to the Trees," "Best Things," and "Gold Fever." There's even a musical number with the Nitty Gritty Dirt Band -- "Hand Me Down That Can o' Beans." Apparently, the budget for Paramount Pictures was incredibly high for the time, estimated to be over $20 million (over $180 million today). The studio even built their own Wild West town for filming in Oregon that cost over $2 million. They seemed to think that considering everyone involved it was a guaranteed hit.
While Marvin nearly saves the film with his strong comedic timing and genuine singing talent, it's clear it's just not Eastwood's thing. Which is interesting, because it wasn't even his first time singing! Rawhide's Clint Eastwood Sings Cowboy Favorites is actually decent and explains why the actor even signed on to appear in a musical in the first place. The movie may have been a flop at the box office with a seriously bizarre plot centered around a polyamorous relationship (true story) but one good thing came from it -- Eastwood started focusing on directing and turned into one of the most celebrated filmmakers of his generation. We'll take it!
Now Watch: Clint Eastwood: Meet the American Icon's 8 Children
Enjoy all things country?
Don't miss a story! Sign up for daily stories delivered to your inbox.