Introduction

Watch Late Legend Toby Keith Perform Breakout Anthem ‘Before It Was A Hit’
The late, great Toby Keith, who passed away in February 2024, left behind a legacy defined by swagger, patriotism, and an unmatched ability to craft indelible anthems. While hits like “Courtesy of the Red, White and Blue” and “I Love This Bar” became stadium staples, it all started with a simple, powerful declaration: “Should’ve Been a Cowboy.”
For fans and music historians, discovering early, raw footage of a legend performing their breakthrough track before it exploded onto the charts offers a unique glimpse into the genesis of stardom. A now-treasured clip circulating online captures just that moment, showcasing Keith’s raw ambition and genuine talent years before he became the global superstar we remember.
The footage, believed to be from a small venue or a television appearance in the early 1990s, presents a younger, perhaps slightly nervous, but intensely focused Toby Keith. He isn’t wearing the designer denim or the signature cowboy hat that would later define his image. Instead, he’s simply a man with a guitar, sharing a story he had just written. The environment is intimate, lacking the polish and explosive production of the final 1993 studio recording that would launch his career into the stratosphere.

What is striking about this early performance is how fully formed the song already was. The powerful, yearning lyrics—detailing a life lived by the codes of the Old West and tipping a hat to icons like Matt Dillon and Gene Autry—were already present, delivered with the booming confidence that would become his trademark. The early rendition is stripped down, allowing the compelling narrative and Keith’s rich baritone voice to take center stage. You can hear the hunger in his voice, the anticipation of a track he clearly knew was special.
“Should’ve Been a Cowboy” didn’t just top the country charts; it crossed over, becoming the most-played country song of the 1990s. This early video, however, reminds us that the song’s brilliance didn’t come from market research or studio wizardry, but from the simple, authentic storytelling of a determined Oklahoma songwriter. It’s a powerful testament to the timeless nature of the music and the genuine grit of the man who created it. Watching him perform it then, you realize the legend wasn’t manufactured—it was merely waiting for the right moment to arrive.