Published by Cel Manero from Global One Media Inc.
The “Need a Favor” artist has covered Keith’s classic multiple times following the passing of the country legend at 62 in February 2024.
Jelly Roll is honoring Toby Keith’s memory.
The 40-year-old country artist helped usher in the new year with a five-song set at Nashville’s Big Bash at Bicentennial Park on December 31. He ended his performance with a heartfelt cover of Keith’s iconic song “Should’ve Been a Cowboy.”
Keith, who passed away at 62 in February 2024 after battling stomach cancer, has been remembered by Jelly Roll, who has included “Should’ve Been a Cowboy” in several of his performances since. During the Big Bash, Jelly Roll’s tribute followed his own songs “I Am Not Okay,” “Need a Favor,” “Son of a Sinner,” and “Liar.”
The New Year’s Eve event also featured performances by 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.
Earlier in April, Jelly Roll teamed up with T-Pain for a duet of “Should’ve Been a Cowboy” at the 2024 Stagecoach Festival in Indio, California. The cover was made available exclusively on Amazon Music before the performance.
In an interview with Variety, Jelly Roll shared how Toby Keith and songs like “Should’ve Been a Cowboy,” “The Next Thing on My List,” and “I Love This Bar” inspired his shift from rap to country music.
“He was an outlier, unapologetically Oklahoma. A lot of what he did encouraged and empowered me,” Jelly explained. “He was highly individualistic, carving his own path from beginning to end. He didn’t know it, but he was a mentor to me just by watching him from a distance.”
Before releasing his cover of the song, Jelly Roll revealed he had received Keith’s son Stelen’s approval. “Toby’s son pulled me aside at the CMTs and told me, ‘Hey man, I’ve seen a video of you covering this song, and I think it’s one of the best versions I’ve ever heard. You really honor my father.’ That meant so much to me,” Jelly said.
One of the reasons Jelly Roll chose T-Pain as his duet partner was the rapper’s personal connection to Toby Keith.
T-Pain shared with Jelly Roll a story about his only major experience in the country music world, when he presented with Toby at the 2009 CMT Awards. T-Pain recalled how Toby made him feel at ease, cracking jokes and ensuring he felt comfortable before they went on stage.
The two decided to donate the proceeds from their cover of “Should’ve Been a Cowboy” to the Toby Keith Foundation. “I figured we were doing this for Toby, and when I called T-Pain about it, he didn’t hesitate,” Jelly Roll said.