Introduction
The country music world was deeply shaken on February 5, 2024, when beloved singer Toby Keith passed away at age 62 after a courageous battle with stomach cancer. Among those mourning his loss was fellow Oklahoma native and country superstar, Carrie Underwood.
Underwood, who shared a strong connection with Keith through their shared roots and mutual respect, offered one of the most moving tributes following his passing. Alongside a collection of heartfelt photos showing their time together over the years, she wrote:
“Saddle up the horses, Jesus, because a true blue COWBOY just made his ride up to heaven! Introduce him to all the Okies and sign that boy up for the choir! We’re gonna miss you, Toby, but my heart has no doubt that you are standing in the presence of our King right now. See you again someday, friend.”
Carrie’s Emotional Opry Performance: “Should’ve Been a Cowboy”
Back in 2022, Carrie had the honor of performing Toby Keith’s iconic debut single, “Should’ve Been a Cowboy,” when he received the BMI Icon Award—an evening that celebrated his influence on generations of artists.
Then, in April 2024—just two months after his death—Carrie stepped into the revered circle of the Grand Ole Opry and once again paid tribute to Toby. As a proud Opry member, she holds every performance there close to her heart. Reflecting on that night, she posted:
“Always a wonderful night when it’s a night at the @opry! I consider myself so incredibly blessed to be a part of this family!”
During that evening’s set, Carrie paused to honor Toby’s legacy by singing “Should’ve Been a Cowboy” once more. This tribute came shortly after an emotional all-star salute to Keith during the CMT Music Awards on April 7, 2024.
What followed was a heartfelt and powerful performance that captured the spirit of Toby Keith’s music and the love he inspired throughout the country music community. Carrie’s voice, steady and sincere, carried the weight of a friend’s goodbye, wrapped in melody and memory.
Watch below as Carrie Underwood pays tribute to Toby Keith with her live performance at the Opry—a moment that stands as a beautiful reminder of the music, the man, and the legacy he leaves behind.