The moment the first guitar strum echoed through the arena, the crowd knew exactly what was coming—and they couldn’t contain their excitement. Cheers erupted as Toby Keith launched into his career-defining hit, “Should’ve Been a Cowboy.” With his signature confidence and unmistakable voice, Keith took the lead, while Blake Shelton—one of today’s biggest country stars—added his smooth harmonies, blending past and present in a way that felt effortlessly perfect.
This wasn’t just a trip down memory lane. It was a full-on celebration of Toby Keith’s enduring influence on country music. Fans sang every single word, their voices rising with each verse. By the time the final chorus hit, the room was buzzing with energy, and the standing ovation that followed was nothing short of thunderous.
The performance was part of the ACM Awards’ special “ACM Throwback” segment, honoring 25 years of country classics. In 2018, Shelton had returned to the ACM stage after a long absence, keeping fans guessing about which song he’d perform. Many expected one of his own recent hits, but instead, he surprised everyone by teaming up with Keith to revive the 1993 anthem. The timing couldn’t have been better—it was also the 25th anniversary of the song’s release, which Keith was celebrating with his “Should’ve Been a Cowboy Tour XXV.”
Together, the two country powerhouses delivered a performance that was pure magic—electric, nostalgic, and overflowing with personality. Social media lit up afterward, with fans calling it one of the best moments of the night. One person summed it up perfectly: “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!”
It was more than just a duet. It was a reminder of why “Should’ve Been a Cowboy” will forever be a staple in country music history—and why Toby Keith and Blake Shelton will always be remembered as two of its greatest voices.
