Jelly Roll Shares Toby Keith Cover Ahead of Stagecoach Debut

Singer drops studio version of “Should’ve Been a Cowboy” featuring T-Pain, who will join Jelly Roll onstage Friday at the Indio, California festival

Ahead of Jelly Roll’s debut performance at Stagecoach Friday night, the country singer has shared his rendition of Toby Keith’s “Should’ve Been a Cowboy,” featuring an assist from T-Pain.

The studio version of the cover, released as part of Amazon Music Originals’ lead-up to Stagecoach, arrives after Jelly Roll spent much of the past year before and after Keith’s February 2024 death playing the 1993 single in concert.

“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.

“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.”

Jelly Roll has already promised to perform “Should’ve Been a Cowboy” at the Indio, California festival Friday, where he’ll be joined by an unlikely guest: T-Pain.

“I love T-Pain and I love his work and I was thinking about who would be a perfect surprise guest for Stagecoach that nobody would see coming,” Jelly Roll told Variety


“I love putting together odd pairings because I think I’m an odd pairing by myself. And I think Toby was kind of all about that too. And then when I got to talking to T-Pain about Toby just in general, 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.”

Proceeds from the “Should’ve Been a Cowboy” cover will benefit the Toby Keith Foundation, which supports the health and happiness of pediatric cancer patients.

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