Jelly Roll Pays Tribute to Toby Keith on New Year’s Eve With Another Emotional ‘Should’ve Been a Cowboy’ Cover

Jelly Roll celebrated the end of the year with another homage of one of his musical heroes. During the Nashville’s Big Bash New Year’s Eve special on Tuesday night (Dec. 31), the singer performed Toby Keith’s 1993 debut single, “Should’ve Been a Cowboy” as part of a five-song set that also included his own hits “I Am Not Okay,” “Need a Favor,” “Son of a Sinner” and “Liar.”

“I would like to dedicate this newt song to one of the greatest country music superstars that ever lived,” Jelly told fans. “In his memory, God rest your soul Big Dog Daddy, Toby Keith baby!”

Jelly has performed “Cowboy” live a number of times since Keith died in February 2024 at age 62 from stomach cancer. He rolled out the cover for the first time at the Stagecoach Festival in April, when he was joined by T-Pain for a run through the song; the pair also dropped a recorded version of the track for Amazon Music.

“I had been covering ‘Should’ve Been a Cowboy’ for about a year now at most of my shows, just kind of honoring Toby as he was getting sick before he passed away,” Jelly Roll, 40, told Variety at the time, noting that he got the blessing to release his version from Keith son, Stelen, who saw a video of Jelly’s version and called it one of the best he’d ever seen. “Then I really started chewing on, man, what better place to honor Toby than Stagecoach? Plus, Toby Keith was one of the artists that from afar, even though he would never have known it, encouraged me to do country music.” Funds raised from the cover were earmarked for the Toby Keith Foundations, which aids pediatric cancer patients.

Jelly Roll was also part of an all-star celebration of Keith’s life at Bridgestone Arena on July 29 taped for the NBC TV special Toby Keith: American Icon, which also featured Luke Bryan, Eric Church, Ashley McBryde, Darius Rucker, Carrie Underwood and many more.