T-Pain, Jelly Roll Honor Toby Keith at Stagecoach 2024 with Iconic Song 2

As a memorial to the late country music legend Toby Keith, vocalist Jelly Roll has released a rendition of Keith’s hit song “Should’ve Been a Cowboy.”

Toby Keith’s passing earlier this year has left country music in mourning. After the star’s passing, tributes began to flood in from all around the music business. Artists from all walks of life, not just country, paid tribute to the late singer. Out of all these tributes, one of the most unexpected yet perfect collaborations has come to light, demonstrating the breadth of Toby Keith’s musical influence.

Jelly Roll, a country musician, teams up with T-Pain, a rapper, for a unique cover song before their Stagecoach Festival performance. They performed a cover version of Keith’s timeless song “Should’ve Been a Cowboy” that was exclusive to Amazon Music. The fact that musicians from all walks of life can unite in this tribute to a legend demonstrates how music can break down barriers.

T-Pain, Jelly Roll Honor Toby Keith at Stagecoach 2024 with Iconic Song 2

Jelly Roll pays tribute to Toby Keith with Should’ve Been a Cowboy cover

Jelly Roll, a country music artist, just dropped a cover version of Should’ve Been a Cowboy, a hit by Toby Keith. T-Pain makes an unexpected cameo, making this cover more special than the average one.

The Stagecoach festival was preceded by the release of the studio version of the cover on Amazon Music Originals. Before and after Keith’s death in February 2024, Jelly Roll performed the song live frequently, leading up to its release.

Toby was dying of illness, so I covered “Should’ve Been a Cowboy” on most of my gigs for the past year as a kind of tribute to him. The thought occurred to me, “Man, Stagecoach would be the perfect location to honor Toby.” Variety spoke with Jelly Roll.

The way he infused his music with his personality was the most important thing. An anomaly, he was. His addition was that he was unabashedly from Oklahoma.

After a heartfelt meeting with Toby Keith’s son, the choice to play the song at Stagecoach took on even more importance. Toby’s kid approached me at the CMTs after seeing me do a rendition of the song and told me, “Hey, dude, I saw a video of you covering this song, and I think it’s one of the best versions of it ever.” I’ve been covering the song for a while now. And I believe you do a tribute to my dad. It had immense personal significance for me.

At the festival, Roll has promised to sing Should’ve Been a Cowboy, and T-Pain will surprise everyone by making an appearance as well. I adore T-Pain and all of his music. Considering who would be the ideal unexpected Stagecoach visitor, Jelly Roll made the observation.

He has made no secret of the fact that Toby Keith was a major influence on his decision to pursue country music.

T-Pain, Jelly Roll Honor Toby Keith at Stagecoach 2024 with Iconic Song 2

Jelly Roll paid tribute to Toby Keith 

Jelly Roll was devastated to hear of Keith’s death in February 2024 and resorted to Instagram to share his feelings of loss. “Toby inspired millions and I was one of them,” said he.

Jelly Roll discussed his choice to honor Keith at Stagecoach in further detail in an interview he gave to Variety. In honor of the dying country legend, he admitted that for the last year he had been performing covers of Keith’s popular song “Should’ve Been a Cowboy” during his concerts. “What better place to honor Toby than Stagecoach?” Jelly Roll asked.

T-Pain, Jelly Roll Honor Toby Keith at Stagecoach 2024 with Iconic Song 2

It was the iconic country singer, he said, who greatly impacted him. According to him, “Toby Keith was one of the artists that from afar, even though he would never have known it, encouraged me to do country music.”

Not only did Jelly Roll remember Keith fondly, but so did T-Pain, another artist and producer with whom he worked. At the 2009 CMT Music Awards, he met the singer and was amazed by “how awesome Toby was just as a human.” Keith put T-Pain at ease and even had him laugh before their public appearance, according to T-Pain.


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