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'He Was An Outlier': Jelly Roll Opens Up About Covering Toby Keith's Should've Been a Cowboy With T-Pain
Singer Jelly Roll has released a special cover of Country music singer Toby Keith's iconic song Should've Been a Cowboy as a tribute to him.
Trigger Warning: This article contains mention of death.
Country music still mourns the death of Toby Keith, who died earlier this year. Tributes had poured in from all corners of the music industry following the star's death. Country singers and artists of other genres spoke of their respect and admiration for the late singer. Among these tributes, one of the most surprising yet fitting collaborations has emerged, showing how much Toby Keith's music has influenced different genres and artists.
Before performing at the Stagecoach Festival, country singer Jelly Roll teams up with rapper T-Pain for a special cover song. They put their own spin on Keith's classic Should've Been a Cowboy, an Amazon Music exclusive. The collaboration shows how music can transcend genres, where artists from different backgrounds come together to honor a legend.
Jelly Roll pays tribute to Toby Keith with Should've Been a Cowboy cover
Country singer Jelly Roll released a special cover of Toby Keith's iconic song Should've Been a Cowboy. This rendition isn't just any ordinary cover, though; it features a surprise guest appearance by artist T-Pain.
The studio version of the cover was released through Amazon Music Originals as part of the lead-up to the Stagecoach festival. This release followed Jelly Roll's frequent live performances of the song, both before and after Keith's passing in February 2024.
“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. Then I really started chewing on, man, what better place to honor Toby than Stagecoach?” Jelly Roll told Variety.
“Just the whole way he put his personality into his music. He was an outlier. He was unapologetically Oklahoma,” he added.
The decision to perform the song at Stagecoach held even more significance after a touching encounter with Toby Keith's son. “I’ve been covering the song, and 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.”
Roll's promise to perform Should've Been a Cowboy at the festival also includes an unexpected guest appearance by T-Pain. "I love T-Pain, and I love his work. I was thinking about who would be a perfect surprise guest for Stagecoach that nobody would see coming," Jelly Roll noted.
He has spoken openly about the impact Toby Keith had on his own journey into country music.
Jelly Roll paid tribute to Toby Keith
The news of Keith's passing in February 2024 deeply affected Jelly Roll, who took to Instagram to express his grief. "Toby inspired millions and I was one of them," he wrote.
In the interview with Variety, Jelly Roll elaborated on his decision to honor Keith at Stagecoach. He revealed that he had been covering Keith's hit song Should've Been a Cowboy at his shows for the past year as a way to pay respect to the ailing country legend. Jelly Roll stated, "What better place to honor Toby than Stagecoach?"
He noted that the legendary country star had a significant influence on him. He explained, "Toby Keith was one of the artists that from afar, even though he would never have known it, encouraged me to do country music."
Jelly Roll's fellow artist and producer, T-Pain, also shared a fond memory of Keith. He recalled meeting the singer at the 2009 CMT Music Awards and being struck by "how awesome Toby was just as a human." T-Pain went on to describe how Keith made him feel comfortable and even cracked him up before their public appearance.
ALSO READ: 'I'm A Big Hugger': Jelly Roll Reveals How He Loves Embracing People In Real Life
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