Toby Keith Passed Away On February 5 Following A Battle With Stomach Cancer

Jelly Roll closed out 2024 by singing “Should’ve Been a Cowboy” in tribute to Toby Keith.

Toby passed away on February 5, 2024 following a years-long battle with stomach cancer. He was 62 years old.

His death sparked tributes from dozens of artists, including Jelly Roll. He sang Toby’s iconic debut single, “Should’ve Been a Cowboy,” at a concert shortly after Toby passed away.

Jelly Roll continued to perform the song live throughout 2024.

Jelly Roll regular performed “Should’ve Been a Cowboy” at his shows before Toby’s passing. But the song took on a new meaning for the “I Am Not Okay” singer after Toby died.

Later, Jelly Roll signed up to participate in the American Icon tribute concert honoring Toby at Nashville’s Bridgestone Arena. The show was filmed for a concert special that aired on NBC.

Jelly Roll performed an emotional rendition of  “My List,” and dedicated it to Toby’s family.

Jelly Roll Sings Toby Keith’s “Should’ve Been A Cowboy” During New Year’s Eve Live: Nashville’s Big Bash

On New Year’s Eve (December 31), many of country music’s biggest stars gathered in Nashville to welcome 2025. They performed during a televised special on CBS called New Year’s Eve Live: Nashville’s Big Bash.

Jelly Roll was one of the performers. His set included his hits “I Am Not Okay” and “Need a Favor.”

But instead of singing one of his own songs to close out 2024, Jelly Roll opted to perform “Should’ve Been a Cowboy” as his last song of the year.

“I would like to dedicate this next song to one of the greatest country music superstars that ever lived, in his memory, God rest his soul.” Jelly Roll said in a video shared by radio station 101.7 The Bull. “Big Dog Daddy, Toby Keith baby!”

@thebull1017 What a class act. An incredible way to honor the legacy #countrymusic #jellyroll #tobykeith #2025 ♬ original sound – 101.7 The Bull

From there, Jelly Roll moved into his energetic cover of “Should’ve Been a Cowboy.” He also held his microphone out to the crowd, so they too could be heard singing Toby’s timeless track.

As of press time, Jelly Roll and CBS have not shared an official video of his “Should’ve Been a Cowboy” cover on New Year’s Eve. But, you can watch a fan-filmed clip below.

Hats off to Jelly Roll for using his final performance of 2024 to honor Toby Keith.

@thetraveladdict.com Jelly Roll brought in the New Year in Nashville with a Toby Keith tribute of “Should’ve Been a Cowboy” at Nashville’s Big Bash. @Jelly Roll #jellyroll #tobykeith #shouldvebeenacowboy #nashville #nashvilletn #nashvillenye #nashvillebigbash #nye #newyearseve #countrymusic #country #coversong #tennessee ♬ original sound – thetraveladdict