Clint Eastwood stood in a vocal booth singing "Sierra Nevada." The year was 1965, and the Rawhide star was in the studio recording a track for All the Hits with All the Stars, Vol. 4, part of a series of compilations albums featuring celebrities belting out popular songs. Clint's tune would close out Side A. He was no stranger to the music business. A few years earlier, the rising Western star had cut an entire album, Cowboy Favorites. He even sang a number called "Rowdy," about his studly Rawhide character. 

However, producer Kal Mann, who was overseeing All the Hits with All the Stars, was not impressed. After Clint crooned "Sierra Nevada," Mann told it to him honest — he would never make it as a singer.

"I know," Clint said, according to Patrick McGilligan's biography Clint: The Life and Legend. "But I'm going to make it big somehow."

Indeed, he did. A shelf loaded with four Oscars and an equal number of Golden Globes attests to that. But Mann was wrong. Clint did, in a way, "make it" as a singer. He earned fat paychecks for concerts, which counts in our book.

When Rawhide took a break from filming, Eastwood and his costar Paul Brinegar, who played the colorful cattle-drive cook Wishbone, would often team up to perform at rodeos and state fairs. 

The Eastwood-Brinegar duo promoted their availability in a 1962 issue of the trade publication Amusement Business Calvacade of Fairs. The advertisement proclaimed the actors were "available individually — as a duo or group." Your local agrarian festival could hire the performers for the mere price of… $15,000 for a single date! 

Gulp. That translates to about $125,000 in today's coin. Pretty sweet money for a guy who would "never make it."

As a bonus, Eastwood and Brinegar were frequently joined by fellow Rawhide star Sheb Wooley, perhaps the most musical member of the most musical Western cast. Wooley was the one, after all, who had scored a No. 1 hit with his novelty tune "The Purple People Eater." The show also welcomed crooning guest stars such as Frankie Laine.

If you're wondering, yes, Clint did demonstrate his pipes on camera for Rawhide. In the episode "Incident of the Hostages," Rowdy strums a guitar sings his signature, "Rowdy."

"I never had a love to call my own / A poor drover's life is always alone," he laments to his audience of Native American children.

A season earlier, he stood on a stage and beautifully sang "Beyond the Sun" in "The Pitchwagon."

Eastwood would go on to compose music for his acclaimed films, including singing the theme song to his hit Gran Torino. In 2007, Eastwood was awarded an honorary Doctor of Music degree from the Berklee College of Music. Yeah, he made it.