On This Day in 1993, Toby Keith Introduced Himself to the Country Music World with His No. 1 Debut Single “Should’ve Been a Cowboy”

On this day (February 12) in 1993, Toby Keith kicked off a career full of hits with his debut single “Should’ve Been a Cowboy.” He wrote and released the song as the first single from his self-titled debut album. The song went to No. 1 on the Billboard Hot Country Songs chart and would go on to become the Oklahoma native’s signature song.

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“Should’ve Been a Cowboy” wasn’t just a debut single. It was an opening salvo from an artist who would dominate the country airwaves throughout the ‘90s and early 2000s. It was also a look at Keith’s singing ability as well as his songwriting—a killer combination that would land him 16 career No. 1 singles.

[RELATED: The Embarrassing Dancefloor Rejection Behind Toby Keith’s Debut Single and First No. 1 “Should’ve Been a Cowboy” ]

“Should’ve Been a Cowboy” climbed to the top of the Billboard Hot Country Songs chart and stayed there for two weeks upon its initial release. Then, after Keith died last February, it was one of five of his songs that re-entered the chart, landing at No. 12 more than 30 years after it first hit the airwaves.

It also became the go-to song for those who wanted to pay tribute to Keith during their concerts. They didn’t have to make a big, sappy speech in honor of the hit-making country star and his legacy. Instead, several artists performed his debut single and everyone understood that it was a nod to Keith and the impact he made on the genre.

The Story Behind Toby Keith’s Debut Hit

Toby Keith wrote “Should’ve Been a Cowboy” while on a hunting trip in Kansas with some friends. After a long day in the woods, he and the guys went to a local watering hole to have a few beers. “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,” Keith recalled. “He was going to show that he could still bust a move,” he added.

The cowgirl told Keith’s newfound friend that she didn’t dance and sent him back to his pals. “About 15 minutes later, a young cowboy comes in—and off they go on the dance floor,” Keith said. “Everybody was making fun of him, and one of the guys said, ‘John, I guess you should have been a cowboy.’”

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