Credit: Far Out / TCM

“That is really tough”: the 1961 song Clint Eastwood wants to delete from history

Sun 3 May 2026 17:45, UK

You can tell that Clint Eastwood always wanted to be a singer, and you can also tell that he’d have never made it if he weren’t an actor, because, as harsh as it sounds, he can’t sing worth a fuck.

There are singers who can act, and there are actors who can sing. Eastwood is neither of those things, but that hasn’t stopped him from chancing his arm in the recording booth on numerous occasions, and all the evidence points to a man who, as iconic as he is, cannot carry a tune under any circumstances.

In 1963, his first album hit the shelves, which sought to capitalise on his growing fame as the star of a popular TV series, while also allowing him to indulge his other dream. Rawhide’s Clint Eastwood Sings Cowboy Favorites is exactly as described, but it didn’t sell very well, and plans for a tour were scrapped.

Did that deter him? Absolutely not. He sang again in Paint Your Wagon, which is every bit as horrific as it sounds, and even the four-time Academy Award-winning icon admitted that a musical western was something he should have listened to his instincts over and walked away while he still had the chance.

He did record a track that hit number one on the country music charts, though, with Bronco Billy‘s ‘Bar Room Buddies’ alongside Merle Haggard, finding plenty of fans among its target audience, while he also duetted with Ray Charles on ‘Beers to You’ from the Any Which Way You Can soundtrack.

Eastwood’s association with crooning would end in 2008 when he growled his way through the title track from Gran Torino that played over the end credits, but it was an early 1960s song that left him wishing it had been permanently consigned to the scrapheap, with the embarrassment palpable when it was played right in front of him.

At the peak of his Rawhide popularity, Eastwood unleashed ‘Unknown Girl of My Dreams’ on an unsuspecting world in 1961, which was his first solo single as a recording artist. It didn’t chart, obviously, but when he heard a snippet of it in 2008, he immediately began suffering from a severe case of full-body cringe.

“Thank you for not playing the whole record,” he acknowledged. “That’s what music was all about in the ’60s. Everything was starting to get into the rock and roll era, and it wasn’t complicated. But you have to… listen, you think looking at yourself on the screen is tough? That is really tough.”

Eastwood wasn’t wrong when he pointed out that “the arrangements are really corny,” but that’s just one of the many problems ‘Unknown Girl of My Dreams’ has, the most notable being that it’s just awful.