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    Home » News » 30 Years Ago Today, Toby Keith’s “Should’ve Been a Cowboy” Went #1

    30 Years Ago Today, Toby Keith’s “Should’ve Been a Cowboy” Went #1

    Brennen KellyBy Brennen KellyJune 5, 2023 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 was released on Feb. 12, 1993, as Keith’s debut single on his debut album, also titled Should’ve Been a Cowboy. It debuted at #69 before rapidly climbing the chart and hitting #1 on June 5, 1993.

    The track is penned independently by Keith and paints a picture of his dreams of being a cowboy. The wistful song laments on how Keith 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. The smash hit has racked up over three million spins on country radio, making it the most-played song on country radio in the 1990s.

    Listen to it here:

    Featured toby keith
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    July 11, 2025

    Zac Brown Band Released Their Grammy-Winning Album “Uncaged” 13 Years Ago Today

    July 10, 2025

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    July 9, 2025

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    July 9, 2025

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