Jelly Roll Opens Up About Covering Toby Keith’s “Should’ve Been a Cowboy” with T-Pain

Today (April 26), Jelly Roll and T-Pain released their cover of Toby Keith’s chart-topping debut single “Should’ve Been a Cowboy” exclusively on Amazon Music. They’ll also take the stage together to perform their rendition of the song tonight when Jelly makes his Stagecoach Festival debut.

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Jelly Roll started covering “Should’ve Been a Cowboy” more than a year ago to honor Toby Keith. Recently, he sat down with Variety to discuss his connection to the song, why he partnered with T-Pain to cover it, and more.

[RELATED: Jelly Roll Throws Down “Folsom Prison Blues” Cover by Johnny Cash at Nashville Honky Tonk]

Jelly Roll on How the Amazon Exclusive Toby Keith Cover Happened

During the interview, Jelly Roll revealed that covering Toby Keith’s signature song for Amazon Music was his idea. “Amazon just came to us and talked to us about partnering for something cool for Stagecoach and, as I was flipping through ideas, I had been covering ‘Should’ve Been a Cowboy’ for about a year now at most of my shows,” he explained. He did so to honor Keith as he fought his illness. Then, continued to do so after he passed away.

“I really started chewing on, man, what better place to honor Toby than Stagecoach? Plus, 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 said. “Just the whole way he put his personality into his music. He was an outlier. He was unapologetically Oklahoma,” he added. “There are a lot of things he did that encouraged me and empowered me. … He never knew it but he was a mentor to me, just watching him from afar.”

Fans will have to buy the track on Amazon Music to hear it. All of the proceeds from the track go to the Toby Keith Foundation.

Why Partner with T-Pain for “Should’ve Been a Cowboy”

When Variety asked Jelly Roll why he chose T-Pain to join him for the cover, he had several reasons. “I love T-Pain and I love his work,” he began. Then, he added that T-Pain would be the perfect surprise guest for Stagecoach because “nobody would see it coming.”

“I love putting together odd pairings,” Jelly Roll explained. “I think I’m an odd pairing by myself. And, I think Toby was kind of all about that too,” he added. “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 music space, at the CMT Awards, he was presenting with Toby. He was just talking about how awesome Toby was just as a human and how Toby made him feel comfortable and was cracking him up before they went out,”

Featured Image by Hubert Vestil/Getty Images

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