Toby Keith's Debut Single "Should've Been a Cowboy" Remains One of His Biggest Hits

The 1993 song spent two weeks at No. 1 and helped establish the country star's signature sound.

Published on Feb. 13, 2026

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Toby Keith's debut single "Should've Been a Cowboy" was released on February 12, 1993 and became one of the biggest hits of his career. The song, which Keith wrote himself, spent two weeks at the top of the Billboard Hot Country Songs chart and helped establish the country star's traditional country sound and storytelling style. The song was inspired by an encounter Keith witnessed at a bar in Kansas, where an older man was rejected by a younger woman before a cowboy swooped in and took her to the dance floor.

Why it matters

"Should've Been a Cowboy" was a breakthrough hit for Toby Keith, setting the tone for his long and successful career in country music. The song's traditional country sound and relatable narrative resonated with fans and helped cement Keith's status as one of the genre's leading artists of the 1990s and 2000s.

The details

Keith wrote "Should've Been a Cowboy" solo, drawing inspiration from an encounter he witnessed at a bar in Kansas after a hunting trip. He saw an older man get rejected by a younger woman before a cowboy came in and swept her onto the dance floor, prompting someone to remark "I guess you should've been a cowboy." The song became the lead single from Keith's self-titled debut album, which was released about two months after the single. "Should've Been a Cowboy" spent two weeks at No. 1 on the Billboard Hot Country Songs chart and helped establish Keith's signature sound of strong songwriting, throwback values, and old-school country traditionalism.

  • "Should've Been a Cowboy" was released on February 12, 1993.
  • Toby Keith's self-titled debut album was released about two months after the single, in April 1993.

The players

Toby Keith

An American country music singer, songwriter, record producer and actor who has released 20 number-one singles and is one of the genre's most successful and influential artists of the past three decades.

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What they’re saying

“He jumps up, and he was probably 45 or 50 back then. And he runs over by a 25-year-old cowgirl, and he says he was gonna show how he can bust a move. She turns him down, and then a few minutes later, he comes back and says she don't dance. So they're giving him a bunch of steam over it.”

— Toby Keith, Singer-songwriter (The Boot)

“So that was not quite 15 minutes later, a young cowboy comes in, and off they go on the dance floor. Everybody's making fun of him. And somebody says, 'John, I guess you should've been a cowboy.'”

— Toby Keith, Singer-songwriter (The Boot)

The takeaway

Toby Keith's debut single "Should've Been a Cowboy" helped establish the country star's signature sound and storytelling style, setting the stage for his long and successful career in the genre. The song's traditional country elements and relatable narrative resonated with fans and cemented Keith's status as one of the leading artists of 1990s and 2000s country music.