Watch Jelly Roll and T-Pain Honor Toby Keith at Stagecoach with “Should’ve Been a Cowboy”

Last night (April 26), Jelly Roll made his Stagecoach Festival debut in style. He invited several guests to join him on the stage. However, for many, the highlight of his set was when he brought T-Pain out for their cover of Toby Keith’s signature hit “Should’ve Been a Cowboy.”

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“Should’ve Been a Cowboy” was Toby Keith’s introduction to the country music world. It was the lead single from his debut album. The single went to No. 1 on the country singles chart, dominated the airwaves, and cemented Keith as a hitmaker and force to be reckoned with. Later, it became his signature song. As a result, it was the best way for Jelly Roll to honor one of his musical heroes on the Stagecoach stage.

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

Jelly Roll and T-Pain also released a recorded version “Should’ve Been a Cowboy.” However, fans will only be able to hear it if they buy the single from Amazon Music. The money goes to a good cause, though. All of the proceeds from sales of the song will go to benefit the Toby Keith Foundation which helps fund treatment for pediatric cancer patients and housing for their families during treatment.

Jelly Roll on Why He Covered “Should’ve Been a Cowboy”

In a recent interview with Variety, Jelly Roll said that he started covering “Should’ve Been a Cowboy” almost a year before Keith passed away. He did so because he loved the song and, more importantly, because he looked up to Keith.

“Toby Keith was one of the artists that—from afar, even though he would never have known it—encouraged me to do country music,” he revealed. “Just the whole way he put his personality into his music. He was an outlier. He was unapologetically Oklahoma,” Jelly added. “There are a lot of things that he did that encouraged me and empowered me. He never knew it but he was a mentor to me, just watching him from afar.”

Featured Image by Amy Sussman/Getty Images for Stagecoach

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