Introduction
In the early spring of 1993, Oklahoma‐born singer-songwriter Toby Keith dropped his debut single, Should’ve Been a Cowboy, and with it he ignited a career that would leave an indelible mark on country music. This song became his breakout anthem long before the rest of the world caught up. It peaked at No. 1 on the Billboard Hot Country Songs chart that June.
But more than just charting, the track achieved what few debut songs ever do: it became the most-played country radio song of the 1990s, with over three million spins and counting.
The phrase “before it was a hit” takes on real meaning here—because in its earliest form, it was just a spirited composition by Keith, reflecting a yearning for freedom and the romanticism of the cowboy life.
The lyric “I should’ve been a cowboy / I should’ve learned to rope and ride” evokes a wistful parallel between the working life of the singer and the legendary Western mythos. The inspiration came from a real-life moment: Keith was in a honky-tonk and watched a highway patrolman try to dance with a woman, get turned down, and the guy sitting nearby quipped, “I guess you should’ve been a cowboy.” That moment stuck.
On record, Keith takes the idea and rolls it into a full-blown anthem of escapism and tough-guy charm.
In that sense, the performance clip of Toby Keith singing “Should’ve Been a Cowboy” in its early form—perhaps before full production, before radio saturation—captures a raw version of a song still breathing. A moment when the melody, lyrics and swagger were sitting on the cusp of something huge. As a throwback video shared by his official channels puts it: “Before it was a hit … it was just a song Toby shared with his friend [Troy Aikman].”
What makes this song’s rise so compelling is that it didn’t rely on gimmicks or crossover pop hooks; instead, it tapped into a core country sensibility—steel guitar, wide open imagery, a cowboy fantasy—but with Keith’s own modern swagger. It became not just his breakout moment, but an enduring part of his legacy. Over the next three decades, Keith would rack up numerous No. 1s, cross‐over hits, and build a reputation as the kind of artist who could straddle tradition and mainstream.
Watching a younger Toby Keith perform this anthem—on stage or in a behind‐the‐scenes clip—is to witness the early spark of what would become a major flame. It’s a reminder: sometimes a song precedes the superstar. And the anthem comes first. To revisit the original performance is to say thanks to that moment when a modest tune became a timeless piece of country music history.
So put on the clip, lean back, and listen to the passion, the twang, the swagger. Because before it was a hit, it was simply a song from a guy in a cowboy hat with big dreams—and it set the stage for everything that followed.