32 Years Ago Today: Toby Keith Released “Should’ve Been a Cowboy” — And It Still Rides Strong 🤠🎶
On February 12, 1993, a then-unknown singer from Oklahoma released his debut single — a twangy, swagger-filled anthem called “Should’ve Been a Cowboy.” Thirty-two years later, that song doesn’t just live on — it rides stronger than ever, etched into the heart of country music history.
Toby Keith, only 31 at the time, had written the song in a hotel room, inspired by a conversation and a few laughs. But what started as a casual idea quickly became a cultural lightning bolt. “Should’ve Been a Cowboy” galloped straight to No. 1 on the Billboard Hot Country Songs chart and would go on to become the most-played country song of the entire 1990s, with over 3 million spins on radio.
“I’d have been a cowboy, baby…”
“Riding my pony on a cattle drive…”
With those opening lines, Toby didn’t just introduce himself — he redefined what it meant to be bold, be proud, and be country.
The song paints a romantic picture of the Old West, referencing classic cowboy icons like Gene Autry and Roy Rogers, and mixing it with modern charm and a bit of mischief. But more than anything, it was an anthem for dreamers — for everyone who ever imagined a life of freedom, grit, and wide-open skies.
What made “Should’ve Been a Cowboy” so special wasn’t just its catchy hook or radio-friendly melody — it was the attitude behind it. It was confident without being cocky, nostalgic without being dusty. And it introduced the world to a voice that would become one of the most recognizable and beloved in modern country music.
Today, the song is more than a hit — it’s a staple. It’s played at rodeos, tailgates, country bars, and military homecomings. It’s been covered by countless artists, quoted on T-shirts, and sung loud by every fan who grew up with it in their bones.
Even after Toby Keith’s passing in 2024, the song has taken on a deeper meaning. For many, it now feels like a spiritual signature — the moment the world first heard that fearless, unapologetic Oklahoma spirit that would carry Toby through a legendary career.
“Every time I hear it now,” one fan posted recently, “I don’t just think of cowboys — I think of Toby. I think of the voice we lost and the fire he left behind.”
And that fire is still burning.
As we mark 32 years since its release, “Should’ve Been a Cowboy” stands tall — not as a relic, but as a reminder of everything country music can be: honest, rough-edged, free-spirited, and proudly unpolished.
It was the first ride.
And it’s still one of the best.
Because Toby Keith didn’t just sing about cowboys —
he became one.