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    Home » News » Toby Keith’s Debut Single, “Should’ve Been a Cowboy,” Went #1 On This Day 31 Years Ago

    Toby Keith’s Debut Single, “Should’ve Been a Cowboy,” Went #1 On This Day 31 Years Ago

    Brennen KellyBy Brennen KellyJune 5, 2024 Country Music
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    Legendary.

    Toby Keith has been a country music staple for the past thirty years. However, there was one hit that started it all for the “Courtesy of the Red, White and Blue“ singer.

    “Should’ve Been a Cowboy,” released on Feb. 12, 1993, was Keith’s debut single off his debut album also titled “Should’ve Been a Cowboy.” It debuted at #69 before rapidly climbing the charts and hitting #1 on June 5, 1993.

    The track was penned independently by Keith and paints a picture of his dreams of being a cowboy. The wistful song laments on how the country legend wishes he would have simply been a cowboy instead of living his seemingly boring life with the chorus singing,

    “I should’ve been a cowboy
    I should’ve learned to rope and ride
    Wearin’ my six-shooter, ridin’ my pony on a cattle drive
    Stealin’ the young girls’ hearts
    Just like Gene and Roy
    Singin’ those campfire songs
    Woah, I should’ve been a cowboy”

    The midtempo track is filled with allusions to famous Westerns, outlaws and actors. Marshall Dillon from Gunsmoke, Jesse James, Gene Autry and Roy Rogers are all featured throughout the song’s lyrics.

    “Should’ve Been a Cowboy” has left a lasting legacy on the world of country music, racking up over three million spins on country radio, making it the most-played country song of in the 1990s. 

    Since Keith’s tragic passing in February, “Should’ve Been a Cowboy” has been performed twice to honor the legendary singer/songwriter. Brooks & Dunn performed the song first at this year’s CMT Awards, followed by Jason Aldean‘s emotional, acoustic performance during the 59th annual ACM’s.

    And although we’ve all seen the music video over a dozen times, what’s one more gonna hurt? RIP big dog daddy.

    toby keith
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    Brandon Lake Responds To Fans Calling Him Out For “Changing” As He Finally Teases Full-Blown Country Era: “Can’t Keep Me Away From The Country Too Long”

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    October 1, 2026

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