Jelly Roll Tributes Late Toby Keith with ‘Should’ve Been a Cowboy’ Cover on New Year’s Eve in Nashville

Jelly Roll keeps Toby Keith’s legacy alive.

The 40-year-old country star helped usher in the new year with a performance of five songs Nashville’s Big blow in the Tennessee capital’s Bicentennial Park on Dec. 31, closing his set with a cover of the late singer’s hit “Should’ve Been a Cowboy.”

Keith died at the age of 62 in February 2024 after being diagnosed with stomach cancer, and Jelly has since performed “Should’ve Been a Cowboy” on several occasions. On Big fight in Nashvillethe tribute came after he sang his own songs “I Am Not Okay,” “Need a Favor,” “Son of a Sinner” and “Liar.”

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Other performers at the New Year’s Eve special included Keith Urban, Kane Brown, Shaboozey, Luke Bryan, Luke Combs, Eric Church, Tyler Hubbard, Miranda Lambert, Post Malone, Brittney Spencer, Chris Stapleton, Lainey Wilson and Zach Top.

In April, Jelly performed “Should’ve Been a Cowboy” as a duet with T-Pain at the 2024 Stagecoach Festival in Indio, California. They previously released the cover exclusively on Amazon Music.

Jelly Roll in December 2024.

Jason Davis/Getty

Jelly Roll performs ‘Should’ve Been a Cowboy’ with T-Pain in honor of the late Toby Keith at 2024 Stagecoach

Talking to Diversity at the time, Jelly explained Keith and songs like “Should’ve Been a Cowboy,” “The Next Thing on My List” and “I Love This Bar” inspired his turn from rap music to the country genre.

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“He was extraordinary. He was unapologetically Oklahoma. There are a lot of things he did that encouraged and empowered me,” he told the newspaper. “He was very individualistic and carved his own path and did it his own way, pillar to post. He never knew it, but he was a mentor to me, I just watched him from afar.”

Before releasing the cover, Jelly said he received the blessing of Keith’s son, Stelen. “Toby’s son saw me on CMT and took me aside and said, ‘Hey man, I want to let you know that I saw your video of you covering this song and I think it’s one of the best versions ever. And I think you respect my father.’ And that just meant a lot to me,” he said.

Toby Keith’s life in photos

Part of the reason he chose T-Pain as his duet partner was the rapper’s relationship with the “Red Solo Cup” musician.

“He was telling me a story about how the only time he did anything big in the country was at the CMT Awards, presenting with Toby [in 2009]. And he was just talking about how great Toby was as a man and how comfortable Toby was and how he was crushing it before they went out,” Jelly said.

Together they decided to donate the proceeds from the cover to the Toby Keith Foundation. “I just realized we were doing it for Toby and the cool thing was I called T-Pain with it and he didn’t hesitate,” the “Save Me” singer added.

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Source: HIS Education

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