At the Grand Ole Opry, Carrie Underwood paid a heartfelt tribute to her late friend Toby Keith, singing his debut hit, “Should’ve Been a Cowboy.” Toby, diagnosed with stomach cancer in 2021, passed away on February 5, 2024, at 62. After his death, tributes poured in from fans, family, and fellow artists. Carrie’s moving message stood out: “Saddle up the horses, Jesus… a true blue COWBOY just made his ride up to heaven.” Two months later, she stepped into the Opry Circle once more, honoring Toby with the same song—one last goodbye to a legend.

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 on Saturday (April 13). 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.