“True legends never fade—they live on in every note we sing and every heart they touch.” Bathed in the gentle glow of the Grand Ole Opry’s timeless stage – Carrie Underwood stepped forward with a reverence that filled the room. Her voice soared through “Should’ve Been A Cowboy,” not merely singing—but breathing new life into Toby Keith’s legacy, “Wrapping his spirit warmly around every listener”. The audience was hushed, expecting a tribute, but instead they were gifted a heartfelt celebration of country music’s very soul—”a tender reminder” that honoring those who paved the way is itself the brightest spotlight of all.
Carrie Underwood Remembers Toby Keith After His Death
Carrie Underwood was one of many country stars devastated by Toby Keith‘s death on February 5, 2024. Keith died at the age of 62 following a battle with stomach cancer.
Both Keith and Underwood were born in Oklahoma.
Underwood penned one of the most powerful tributes to Keith after his death. She shared several photos of them together through the years and wrote:
“Saddle up the horses, Jesus, ’cause 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.”
Watch Carrie Underwood Sing “Should’ve Been A Cowboy” At The Opry
In 2022, Carrie Underwood honored Toby Keith when he received the BMI Icon Award. She performed his debut single, “Should’ve Been a Cowboy,” during the ceremony.
In the wake of Keith’s death, Underwood revisited the song to honor him again.
Underwood performed at the Grand Ole Opry in April 2024, just two months after Keith died. As an Opry member, Underwood treasures every second she spends in “the circle.”
“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!” Underwood wrote on Instagram after her April performance.
During her set, Underwood paused to honor Keith with a cover of “Should’ve Been a Cowboy.” The performance came less than a week after Keith received an all-star tribute during the CMT Music Awards on April 7, 2024.
Head below to watch Carrie pour her heart into “Should’ve Been a Cowboy.” It was a touching tribute to Toby Keith and the legacy he left behind…
Toby Keith was the founder of the Toby Keith Foundation. The foundation helps support the OK Kids Korral, which serves as a home-away-from-home for families with children undergoing cancer treatments. If you’d like to make a donation in Toby’s memory, you can visit the Toby Keith Foundation’s official website.
