Of course, Jelly Roll has turned Toby’s iconic track “Should’ve Been A Cowboy” into a regular feature of his live performances, but what made this tribute even more memorable was the unexpected collaboration with renowned rapper T-Pain.

T-Pain appeared on stage during Jelly’s performance of a rap medley. The medley included DJ Khaled’s track “All I Do Is Win,” which features T-Pain, and T-Pain’s own iconic track, “Buy U A Drank,” adding a surprising twist to the country music event.

Then, he stuck around for the tribute to the country legend and delivered a verse of his own alongside Jelly.

As the song started, Jelly Roll yelled out, “We love you, Toby!”

Watch their performance of “Should’ve Been A Cowboy” below.

Jelly Roll recently released his cover of Toby Keith’s “Should’ve Been A Cowboy” for an Amazon Music Originals exclusive. The release comprises both the studio version and his festival performance with T-Pain, with all proceeds benefiting The Toby Keith Foundation, which serves as a home-away-from-home for families with children undergoing cancer treatments.

The unexpected collaboration between Jelly Roll and T-Pain not only delighted the audience at Stagecoach but also generated buzz within the country music community.

“This is what we all needed but never knew it until now.”
“Omg love this, they knocked it out of the park…You made Toby proud.”
“I believe T-Pain when he says ‘I Should’ve Been A Cowboy.’”
“Love it… I need a real cover from them now….”

T-Pain has explored the realm of country music, showcasing his vocal prowess with the release of a rendition of “Tennessee Whiskey” on his 2023 album, On Top of The Covers.

Despite his widespread association with autotune in his music, T-Pain pleasantly surprised audiences by delivering a remarkable performance, highlighting his exceptional singing abilities.