Introduction
On December 17, 1993, the country music landscape changed forever when a former oil field worker from Oklahoma named Toby Keith secured his first-ever No. 1 hit on the Billboard Hot Country Songs chart. The song, “Should’ve Been a Cowboy,” wasn’t just a chart-topper; it became the foundation of a legendary career and eventually earned the title of the most-played country song of the 1990s on radio.
The Story Behind the Song
Before the glitz of Nashville, Toby Keith Covel was playing bars with his Easy Money Band and working in the grueling Oklahoma oil fields. The inspiration for his debut single came from an unexpected moment in a hotel hunting trip. Keith watched a friend get rejected by a woman in a bar, and someone joked, “He should’ve been a cowboy.”
Keith took that line to heart. He reportedly wrote the song in a bathroom of that same hotel in about 20 minutes. The lyrics tapped into a deep American nostalgia, referencing iconic Western figures like Gene Autry, Roy Rogers, and the classic TV show Gunsmoke. It offered a romanticized escape from the complexities of modern life, longing for a world of “six-shooters” and “trail bosses.”
A Meteoric Rise
Released as his debut single from his self-titled album under Mercury Records, the track moved with incredible speed. In an era where debut artists often struggled for airplay, “Should’ve Been a Cowboy” resonated instantly with listeners.
The song’s success was driven by its:
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Authenticity: Keith’s booming baritone felt rugged and genuine.
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Catchy Hook: The “yippee-ki-yay” refrain was an instant earworm.
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The 90s Country Boom: The song arrived right as country music was exploding into the mainstream, led by the “Class of ’89” (Garth Brooks, Alan Jackson, etc.).
By the time it hit No. 1 on December 17, it had solidified Keith as a force to be reckoned with. It spent two weeks at the top of the charts and paved the way for three more Top 5 hits from his debut album alone.
Lasting Legacy
The impact of “Should’ve Been a Cowboy” extended far beyond 1993. According to BMI, the song eventually surpassed six million spins on the radio. To put that in perspective, if you played the song six million times back-to-back, it would play for over 30 years straight.
It became an anthem for the Oklahoma State Cowboys, played at sporting events to fire up the crowd, and remained a staple of Keith’s live shows until his passing in early 2024. For many fans, the song represents the “Goldilocks” era of country music—blending traditional Western themes with modern production.
Video
Lyrics
🎵 Let’s sing along with the lyrics! 🎤
I bet you’ve never heard ol’ Marshal Dillon sayMiss Kitty, have you ever thought of runnin’ away?Settlin’ down, would you marry meIf I asked you twice and begged you, pretty please?She’d have said, “Yes”, in a New York minuteThey never tied the knot, his heart wasn’t in itHe just stole a kiss as he rode awayHe never hung his hat up at Kitty’s placeI should’ve been a cowboyI should’ve learned to rope and rideWearin’ my six-shooter, ridin’ my pony on a cattle driveStealin’ the young girls’ heartsJust like Gene and RoySingin’ those campfire songsWoah, I should’ve been a cowboyI might of had a sidekick with a funny nameRunnin’ wild through the hills chasin’ Jesse JamesEnding up on the brink of dangerRidin’ shotgun for the Texas RangersGo west young man, haven’t you been told?California’s full of whiskey, women and goldSleepin’ out all night beneath the desert starsWith a dream in my eye and a prayer in my heart