Jelly Roll Performs 'Should've Been a Cowboy' with T-Pain in Tribute to Late Toby Keith at 2024 Stagecoach
Jelly said T-Pain "would be a perfect surprise guest for Stagecoach that nobody would see coming" in an interview before his performance at the music festival
Jelly Roll used his 2024 Stagecoach set to honor the late Toby Keith — with a little help from T-Pain.
The "Need a Favor" singer, 39, performed at the Indio, California, country music festival on Friday and delivered a rendition of Keith's "Should've Been a Cowboy" with a surprise guest appearance from T-Pain in tribute to Keith, who died at age 62 in February following his stomach cancer diagnosis.
Earlier in his set, Jelly was joined by ERNEST and Maddie & Tae for duet versions of "Son of a Sinner" and a brand-new song called "Liar," respectively, before T-Pain hit the stage. The pair began with a cover of DJ Khaled's "All I Do Is Win," which features the "Bartender" rapper, 39, before launching into their cover of Keith's 1993 hit.
Related: Toby Keith's Life in Photos
Ahead of the cover's onstage debut, Jelly and T-Pain released their version of "Should've Been a Cowboy" exclusively on Amazon Music. In an interview with Variety, the "Save Me" musician said he was inspired to remake the song after performing it several times on tour in tribute to Keith.
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Jelly explained that Keith and songs like "Should’ve Been a Cowboy," "The Next Thing on My List" and "I Love This Bar" inspired him to pursue country music following years as a rapper.
"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."
Keith's son, Stelen, had previously give Jelly his stamp of approval on the cover. "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.
When planning for Stagecoach, Jelly wanted to feature a guest "nobody would see coming" and thought of T-Pain, who has a personal connection to Keith.
"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 of the rapper.
Having been a fan of T-Pain's On Top of the Covers project featuring a version of Chris Stapleton's "Tennessee Whiskey," Jelly knew he'd be more than capable of singing "Should've Been a Cowboy."
They also agreed 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 Grammy-nominated country performer.
Elsewhere during his Stagecoach set, Jelly brought out his daughter, Bailee, to sing "Happy Birthday" with his wife, Bunnie Xo, and the crowd in honor of her 16th birthday. "In, like, 10 days, she will be 16 years old," he said. "But hey, I figured it would be a really cool dad way to embarrass her if I can do the old 'Happy birthday to you.'"
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