The onscreen humiliation Clint Eastwood refused to repeat: “I vowed I’d never do that again”

Movie stars have rarely come cooler than Clint Eastwood in his pomp, with the actor exuding effortless charisma and inspiring a thousand imitators. Still, he wasn’t above making an arse of himself onscreen, even if he swore he’d never let the same thing happen twice.

The industry icon’s shadow looms so large over cinema that he continues to inspire performances from his spiritual successors, male and female. Carrie-Ann Moss’ Trinity, Meryl Streep’s Miranda Priestly, Hugh Jackman’s Wolverine, Dwayne Johnson’s Black Adam, Mel Gibson’s Max Rockatansky, Angelina Jolie’s Fox, and Star Wars’ Boba Fett were all inspired by Eastwood, which is an eclectic spread.

His imposing physicality, piercing gaze, thousand-yard stare, curled sneer, and mastery of the grizzled one-liner have enshrined several of his greatest roles in industry folklore, with Quentin Tarantino going so far as to brand him the “sexiest motherfucker” to ever grace the silver screen. In short: he’s cool as fuck.

However, anyone can lose a dangerous amount of cool points if they do something they’re abjectly bad at, as Eastwood discovered to his detriment when he opted to sing for his supper in 1969’s Paint Your Wagon. He knew he was fighting a losing battle on set, and when the end results were shared with the world, he wasn’t the only person who thought it was the single most embarrassing performance of his career.

Not to put too fine a point on it, but the four-time Academy Award winner can’t sing for shit. That hasn’t stopped him from repeatedly trying to prove otherwise, though, with Paint Your Wagon hardly his first or last attempt. He released an album of cowboy songs during his Rawhide days, landed a number one country hit when he warbled ‘Bar Room Buddies’ with Merle Haggard on the Bronco Billy soundtrack, and duetted with Ray Charles on ‘Beers to You’ for Any Which Way You Can.

After being mercilessly dragged for his woeful attempts at convincing the public he had the chops to take top billing in a musical, Eastwood did the world a huge favour by never singing onscreen again. Even when he contributed to a soundtrack as a vocalist for the first time in almost three decades, he made sure his Gran Torino ditty played over the end credits.

Then again, in an interview with The Scotsman, a nerve was struck when the closing track was referred to as singing, with Eastwood interjecting to make it known that once was more than enough, and whatever he’s been doing in the recording booth ever since was a different discipline: “I vowed I’d never to that again,” he said.

Technically, he hasn’t. He’s released a couple of singles, but he hasn’t gone all-out to deliver a showstopping number in a film since 1969. Not that he completely abandoned his musical proclivities, with the legendary star focusing on composing instead and arranging the score for seven of his features, which is a damned sight better than hearing him garble his way through another song. Once was enough, and audiences will be forever grateful.

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