As soon as the first chords rang out, the audience erupted in cheers, recognizing the legendary hit that launched Toby Keith’s career. With his signature swagger and unmistakable voice, Keith led the way, while Shelton—one of country’s modern superstars—added his own smooth vocals, creating a perfect harmony that bridged generations of country music.
The performance wasn’t just about nostalgia; it was a celebration of Keith’s lasting impact on the genre. Fans sang along to every word, reliving the magic of the 1993 classic that has stood the test of time. By the final chorus, the energy in the room was electric, and as the duo wrapped up their unforgettable duet, they were met with a roaring standing ovation.
It was a moment that reminded everyone why Should’ve Been a Cowboy remains one of country’s most beloved anthems—and why both Toby Keith and Blake Shelton are true legends of the genre.
In 2018, Blake Shelton graced the ACM Awards stage for the first time in a long while, stirring excitement among fans about his choice of song for the occasion. There was much speculation about which hit song he would perform, with guesses ranging from his recent single “I Lived It” to the award-nominated “I’ll Name the Dogs.”
However, Shelton took everyone by surprise by choosing a classic tune for a special performance. Teaming up with country music legend Toby Keith, they delivered a nostalgic performance for the ACM’s “ACM Throwback” segment, celebrating the 25th anniversary of hits from 1993.
Their collaboration brought Keith’s debut hit, “Should’ve Been a Cowboy,” back to the limelight. This performance was particularly special as it coincided with the 25th anniversary of the song, which Keith was commemorating with his “The Should’ve Been A Cowboy Tour XXV.”
The duo’s performance at the ACM Awards was nothing short of electrifying, with the audience on their feet, singing along, and applauding enthusiastically. It was clear that Shelton and Keith’s rendition of “Should’ve Been a Cowboy” stood out as a highlight of the evening, demonstrating their seamless chemistry and shared talent in a performance that was both epic and unforgettable.
Feedback from the performance was overwhelmingly positive, with many fans taking to social media to express their excitement. Comments ranged from accolades for the night’s standout moment to heartfelt messages for Toby Keith, highlighting the deep impact of their joint performance.
One viewer noted, “Based on crowd and viewer response, this collaboration was one of the best things to happen on the stage that night!”
Another fan expressed a more personal sentiment, saying, “My two favorites on the stage together. Man I’m sure gonna miss you Toby! Have fun playing music with those angels! See you again someday Big Guy!”