Jelly Roll’s Emotional Tribute to Toby Keith at Stagecoach Leaves Crowd—and Blake Shelton—in Tears

When Jelly Roll took the Stagecoach Festival stage, fans expected a high-energy set—but no one was prepared for the deeply moving tribute that followed. As he began singing Should’ve Been A Cowboy, his voice carried an undeniable weight of emotion, turning the performance into a powerful homage to the late Toby Keith. The raw sincerity in every lyric resonated through the crowd, creating a moment of collective reflection and respect. As the final note hung in the air, the audience stood in silence, overcome by the tribute’s depth. Even Blake Shelton couldn’t hold back his tears, visibly shaken by the heartfelt performance.

Country music artist Jelly Roll brought a touch of surprise and nostalgia to the Stagecoach Festival in Indio, California, as he performed a heartfelt tribute to the late Toby Keith.

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.

Watch him sing “Tennessee Whiskey” below!