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

The “Need a Favor” singer has performed Keith’s hit on several occasions since the late country icon’s death at age 62 in February 2024

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Updated on January 2, 2025 11:25PM EST

Jelly Roll is keeping Toby Keith‘s legacy alive.

The 40-year-old country star helped ring in the new year with a five-song performance during Nashville’s Big Bash at the Tennessee capitol’s Bicentennial Park on Dec. 31, closing out his set with a cover of the late singer’s hit “Should’ve Been a Cowboy.”

Keith died at age 62 in February 2024 following a stomach cancer diagnosis, and Jelly has performed “Should’ve Been a Cowboy” on several occasions since. At Nashville’s Big Bash, the tribute came after he sang his own tracks “I Am Not Okay,” “Need a Favor,” “Son of a Sinner” and “Liar.”

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Other performers on 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. Beforehand, they released the cover exclusively on Amazon Music.

Speaking with Variety 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 pivot from rap music to the country genre.

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

Before releasing the cover, Jelly said he got the blessing of Keith’s son, Stelen. “Toby’s son saw me at the CMTs and took me to the side and said, ‘Hey man, I want to let you know I’ve seen a video of you covering this song, and I think it’s one of the best versions of it ever. And I think you honor my father.’ And it just meant so much to me,” he said.

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Part of the reason he chose T-Pain as a duet partner was the rapper’s connection to the “Red Solo Cup” musician.

“He was telling me the story about how the only time he’s ever done something big in the country space, at the CMT Awards, he was presenting with Toby [in 2009]. And he was just talking about just how awesome Toby was just as a human and how Toby made him feel comfortable and was cracking him up before they went out,” said Jelly.

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