Carrie Underwood Sings “Should’ve Been a Cowboy” in Emotional Opry Tribute to Toby Keith

Carrie Underwood delivered one of the most heartfelt performances of her career when she honored Toby Keith at the Grand Ole Opry with his signature song, “Should’ve Been a Cowboy.” The tribute came just two months after Keith’s passing and resonated deeply with fans across the country—especially in Oklahoma, the home state both artists proudly shared.

Underwood and Keith’s bond extended beyond music. They were kindred spirits shaped by the same roots, the same values, and the same love for country storytelling. After Keith’s death, Underwood shared a moving message alongside throwback photos of the two together:

“Saddle up the horses, Jesus, ’cause a true blue COWBOY just made his ride up to heaven!!! … 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.”

Those words captured what millions of fans felt—gratitude for a legend and grief for a voice that defined an era.

A Song That Defined a Legacy

“Should’ve Been a Cowboy” launched Toby Keith’s career in 1993 and went on to become one of the most-played songs in country radio history. It celebrated dreams, freedom, and the timeless pull of the American West—values Keith embodied throughout his life and career.

Carrie Underwood had previously honored Keith with the song in 2022 when he received the BMI Icon Award. In the wake of his passing, she returned to it once more, this time at the Grand Ole Opry, where emotion filled every note.

As an Opry member, Underwood has often spoken about what “the circle” means to her:

“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 her April 2024 performance, she paused her set and dedicated the song to Keith. The timing made the moment even more powerful—it came less than a week after Toby Keith received an all-star tribute at the CMT Music Awards.

What followed was not just a performance, but a farewell. Underwood poured her heart into every lyric, honoring the man who helped shape modern country music and inspired generations of artists.

 

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A Moment Fans Will Never Forget

The Opry audience stood in silence, many in tears, as Underwood carried Keith’s legacy through his own words. It was a reminder of what country music does best: tell real stories, preserve memories, and keep legends alive.

Carrie Underwood’s tribute ensured that Toby Keith’s spirit—and his cowboy heart—will ride on forever.