Keith released the self-penned “Should’ve Been a Cowboy” as the first single from his self-titled debut album in 1993. The song topped the Billboard Hot Country Songs chart. It also broke into the publication’s all-genre Hot 100 chart, peaking at No. 93.

. @carrieunderwood honored the late @tobykeith at the Grand Ole Opry, performing “Should’ve Been a Cowboy” 🤠 pic.twitter.com/D2db1iQBcP

— CMU Fan ♡ (@TeamCarrie1212) April 14, 2024

Carrie Underwood Nails “Should’ve Been a Cowboy”

Underwood took the Opry stage in a sparkling blue dress and knocked her cover of “Should’ve Been a Cowboy” out of the park. One of the highlights of the overall stellar performance comes just before she moves into the second chorus. After being relatively restrained throughout the first two verses, Underwood shows a fraction of her vocal power with a big, extended note before launching into the chorus.

Toby Keith on the Inspiration Behind His Debut Single

In an interview with Billboard, Keith revealed the inspiration for his debut chart-topper. He recalled being in Dodge City, Kansas at a Gunsmoke-themed bar when he watched a guy get rejected by a cowgirl.

“I think we were actually at the Long Branch Saloon or Miss Kitty’s Saloon—it was something to do with Gunsmoke,” he recalled. “This highway patrolman who I had met on the trip, his name was John, he jumps up. He was probably 45 or 50 back then, and he runs over to this 25-year-old cowgirl. He was going to show her that he could bust a move,” Keith added.

“She turns him down. He comes over and said, ‘She says she doesn’t dance,’” he continued. However, about 15 minutes later, a young cowboy comes in, walks over to the same young lady, and they headed out to the dancefloor. “Everybody was making fun of him,” Keith recalled. “One of the guys said, ‘John, I guess you should have been a cowboy.’”

Then, Keith went into songwriting mode. “I thought, ‘I betcha never heard Marshall Dillon have any woman problems because Miss Kitty was always knocking his back door down.’ I just started writing it and it grew into Jesses James riding shotgun, and Gene and Roy. It all happened in about 20 minutes,” he concluded.

It only took him 20 minutes to write “Should’ve Been a Cowboy” and more than thirty years later, it’s still a certified banger.