Jelly Roll And T-Pain’s Soulful Take On “Should’ve Been A Cowboy” Honors Toby Keith

Jelly Roll took the Stagecoach Festival crowd by surprise with a heartfelt tribute to the late Toby Keith. As he stepped onto the stage, the audience roared with excitement, unaware of the emotional moment about to unfold. When the opening chords of “Should’ve Been A Cowboy” rang out, his deep, soulful voice carried through the night, paying homage to a country legend. With every note, the tribute felt personal, a powerful reminder of Toby Keith’s lasting impact on country music.

The tribute took an unexpected turn when rapper T-Pain joined Jelly Roll on stage for a high-energy medley. The crowd erupted as Jelly rolled into DJ Khaled’s “All I Do Is Win,” with T-Pain seamlessly jumping in to perform his signature hook. The surprise didn’t stop there—T-Pain stayed on to deliver a verse alongside Jelly Roll in honor of the late country legend. As the song kicked off, Jelly Roll’s heartfelt shout—“We love you, Toby!”

The performance was a deeply emotional farewell to the late Toby Keith. Every lyric carried a sense of loss and gratitude, filling the air with raw emotion. As the final chords faded, a heavy silence fell over the audience, each person absorbing the weight of the moment. Among them, Blake Shelton, visibly moved, wiped away tears, overwhelmed by the power of the heartfelt tribute.

The video of their performance has reached 1.7 million views and received tons of positive comments. One wrote, “I love this! So well done! I bet T Pain never thought he’d sing this song but here we are. I love how things like this bring people together. Music brings people together.”

Another chimed in, “To be two nontraditional country music artists, that has to be one of the best cover renditions I have heard. They went out there to do that song and the man that made it famous, I can dig it.”