Jelly Roll in St.Louis, MO on June 21, 2023 by Laura ord

Jelly Roll Teams Up with T-Pain to Cover a Toby Keith Classic

April 26, 2024 6:10 pm GMT

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Since his passing in early February, the tributes to Toby Keith have been pouring in from the country music community and beyond. The latest act to pay homage to the country great may just be the unlikeliest pairing yet, but perhaps the most perfect.

In partnership with Amazon Music just ahead of their Stagecoach appearance tonight (April 26), country sensation Jelly Roll and hip-hop icon T-Pain joined forces to deliver a rendition of the late legend's 'Should've Been A Cowboy.'

Of the partnership, Jelly Roll explained in a recent interview with Variety, "Amazon just came to us and talked to us about partnering for something cool for Stagecoach and, as I was flipping through the ideas, 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?'"

The late artist and his music have meant a lot to the Whitsitt Chapel star over the course of his career. "Toby Keith was one of the artists that from afar," he shared, "even though he would never have known it, encouraged me to do country music."

He continued, "Just with songs like 'Should’ve Been a Cowboy' or 'The Next Thing on My List' and 'I Love This Bar' — just the whole way he put his personality into his music. He was an outlier. He was unapologetically Oklahoma. There are a lot of things he did that encouraged me and empowered me. 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."

Jelly Roll's decision to collaborate with T-Pain came about just as naturally as his decision to honor his hero. "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," he explained. "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."

But it turns out the hip-hop star was no stranger to Keith either. Jelly Roll added, "[T-Pain] 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."

The pair will reportedly perform their rendition of 'Should've Been A Cowboy' during Jelly Roll's set tonight at Stagecoach. All of the proceeds from the Amazon Music Original will go toward benefitting the Toby Keith Foundation, a nonprofit on a mission to support pediatric cancer care.

For more on Jelly Roll, see below:

Written by Alli Patton
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