T-Pain Lands on Billboard’s Country Charts Thanks to Collaboration With Jelly Roll

Spending a quarter of a century in the music industry, T-Pain dabbled in genres like hip-hop and R&B. Releasing a total of seven albums throughout his career, the singer helped bring auto-tune into the mainstream. Besides producing numerous hit songs, he also helped other stars like Travis Scott, Kanye West, and Lil Wayne popularize the effect of auto-tune. But while known for his time in pop, the singer recently shocked the industry when he landed on Billboard’s Country Chart thanks to his collaboration with country singer Jelly Roll. 

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Performing at Stagecoach, Jelly Roll wanted to make the night extra special by not putting the spotlight on him – but Toby Keith. Holding a special place in country music, Keith sadly passed away on February 5, 2024, after battling stomach cancer for several years. With countless stars honoring the icon, the Country Music Hall of Fame inducted him. For Jelly Roll, there seemed no better time to honor Keith than on the Stagecoach stage. And wanting to sing Keith’s hit song “Should’ve Been a Cowboy”, Jelly Roll welcomed none other than T-Pain to the stage. 

[RELATED: T-Pain’s “War Pigs” Cover Receives an All-Time Stamp of Approval From Ozzy Osbourne]

T-Pain Enters Country Music Thanks To Stagecoach

With T-Pain covering songs from all genres in recent months, the singer dazzled on the stage. But his moment didn’t end there as he made his debut on the Hot Country Songs chart. Opening at No. 50, it appears country fans can’t get enough. And thanks to both T-Pain and Jelly Roll, they made sure fans not able to attend Stagecoach got a chance to hear the song. The pair released their cover just one day before they took the stage. 

Having shared time with T-Pain, Jelly Roll explained how the singer shared a connection with Keith that made his performance come full circle. “He was telling me the story about how the only time he’s ever done something big in the country space, at the CMT Awards, he was presenting with Toby [in 2009]. And he was just talking about just how awesome Toby was just as a human and how Toby made him feel comfortable and was cracking him up before they went out.”

Besides fans loving the cover, it seems that even Keith’s son, Stelen, praised the hit. Jelly Roll revealed, “Toby’s son saw me at the CMTs and took me to the side and said, ‘Hey man, I want to let you know I’ve seen a video of you covering this song, and I think it’s one of the best versions of it ever. And I think you honor my father.’ And it just meant so much to me.”   

(Photo by Amy Sussman/Getty Images for Stagecoach)

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