Late Country Legend's First No. 1 Hit Is Still Making Country Music History
On what would have been Toby Keith's 65th birthday, fans are remembering the country icon through the song that started it all.
Long before hits like "Courtesy of the Red, White & Blue," "Beer for My Horses" and "As Good as I Once Was," Keith introduced himself to country music with "Should've Been a Cowboy." Released in 1993 as his debut single, the song quickly climbed to No. 1 on the Billboard Hot Country Songs chart, launching a career that would span more than three decades.
But its success didn't end there.
"Should've Been a Cowboy" went on to become the most-played country song of the 1990s on radio, racking up more than three million spins and cementing its place as one of the defining songs of the decade. More than 30 years after its release, the track remains one of Keith's signature songs and continues to find new audiences.
Fans are still celebrating the song online.
On Reddit, fans are calling the Keith tune "one of many of his best songs!"
"The older I get the more I appreciate his older music and purposefully try to forget his newer stuff," another added.
"I'll always love this one," another fan chimed in. "One of the few songs I can recite nearly every word without hearing a lick of it."
Others called the song their "go-to" for karaoke.
Keith once revealed the inspiration for the song came after watching an older man get turned down for a dance at a bar, only to see a younger cowboy arrive moments later and win the woman's attention. The moment sparked the now-famous title and eventually became one of country music's biggest crossover hits.
Keith died on Feb. 5, 2024, at age 62 after battling stomach cancer. However, his music continues to resonate with fans old and new.
Following his death, "Should've Been a Cowboy" returned to the country charts, a testament to the enduring popularity of the song that introduced the world to one of country music's biggest stars.
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This story was originally published July 7, 2026 at 9:15 PM.