Jelly Roll and T-Pain Honor Toby Keith With ‘Should’ve Been a Cowboy’ Performance [WATCH]

Jelly Roll was joined by T-Pain for a special tribute to Toby Keith while at Stagecoach music festival. The two performed “Should’ve Been a Cowboy,” Keith’s debut single and first No. 1 hit.

Jelly Roll and T-Pain released the song the same day they performed it, as part of an Amazon Music Originals exclusive.

“Amazon just came to us and talked to us about partnering for something cool for Stagecoach,” Jelly Roll told Variety. “And, as I was flipping through the ideas, I had been covering ‘Should’ve Been a Cowboy’ for about a year now at most of my shows, just kind of honoring Toby as he was getting sick before he passed away.”


“Then I really started chewing on, man, what better place to honor Toby than Stagecoach?” he continued. “Plus, Toby Keith was one of the artists that from afar, even though he would never have known it, encouraged me to do country music.”

Few artists have inspired Jelly Roll as much as Keith has, which is why it felt so important for him to honor the future Country Music Hall of Fame member during his Stagecoach performance.

“With songs like ‘Should’ve Been a Cowboy’ or ‘The Next Thing on My List’ and ‘I Love This Bar’ — just the whole way he put his personality into his music. He was an outlier,” Jelly Roll explains. “He was unapologetically Oklahoma. There are a lot of things he did that encouraged me and empowered me. He was very individualistic and carved his own path and he did it his own way, from pillar to post. He never knew it, but he was a mentor to me, just watching him from afar.”

T-Pain might not have seemed like the obvious choice to join Jelly Roll on a country music classic, which is exactly why Jelly Roll chose him.

“I love T-Pain and I love his work, and I was thinking about who would be a perfect surprise guest for Stagecoach that nobody would see coming,” the “Save Me” singer says. “I love putting together odd pairings, because I think I’m an odd pairing by myself. And I think Toby was kind of all about that too. And then when I got to talking to T-Pain about Toby just in general, 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,” he added.

Photo Credit: Getty Images for CMT


Even before Jelly Roll’s Stagecoach performance, he had already earned the respect and appreciation of Keith’s family for his take on “Should’ve Been A Cowboy,” including Keith’s only son, Stelen.

“I’ve been covering the song, and Toby’s son saw me at the CMT [Awards] 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,'” Jelly Roll shared. “And it just meant so much to me.”

Proceeds from Jelly Roll and T-Pain’s “Should’ve Been A Cowboy” collaboration will go to the Toby Keith Foundation. Download or stream the song at Find all of Jelly Roll’s music and upcoming shows at

Read ‘Jelly Roll: 11 Things to Know About the Reformed Singer’ here.

Photo Credit: Courtesy of Stagecoach / J. Bernstein