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

Jelly Roll paid tribute to Toby Keith again on New Year's Eve with another cover of the late country icon's debut single, 'Should've Been a Cowboy.'

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.” 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.

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