Jelly Roll, T-Pain pair for cover of Toby Keith's 'Should've Been A Cowboy' at Stagecoach

Just in time for 2024's superstar-struck and crossover-appealing Stagecoach Festival, Jelly Roll and T-Pain have joined forces for a sing-a-long-ready cover of recently deceased forthcoming Country Music Hall of Fame inductee Toby Keith's iconic 1993 hit "Should've Been A Cowboy."

Jelly Roll will also perform the song during his April 26 Stagecoach set from 8:10-9 p.m. PT / 10:10-11 p.m. CT. His set and many sets during the weekend in Indio will be broadcast exclusively on Amazon Music channel on Twitch and Prime Video.

The Nashville native is donating all proceeds from the Amazon Music Original to the Toby Keith Foundation, supporting pediatric cancer patients' health and happiness.

The pairing of Jelly Roll and T-Pain on a Toby Keith single also highlights the broad growth of country's appeal. No fewer than five years ago, both artists were far better renowned for their hip-hop exploits than anything remotely related to three chords and the truth.

However, in 2023, T-Pain evolved his talents behind six Grammy awards and 10 all-genre Billboard Hot 100 singles to the realm of releasing a covers album including Chris Stapleton's Tennessee Whiskey" alongside Sam Cooke's "A Change Is Gonna Come," Journey's "Don't Stop Believin'," Dr. Hook's "Sharing The Night Together," Sam Smith's "Stay With Me," Frank Sinatra's "That's Life" and Black Sabbath's "War Pigs."

Upon hearing of Keith's passing in Feb. 2024, Jelly Roll shared condolences and sorrow in an Instagram story. "Toby inspired millions and I was one of them."

To Variety, Jelly Roll added,

"Amazon just came to (T-Pain and me) and talked to us about partnering for something cool for Stagecoach 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? 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."

Regarding T-Pain, the artist and producer noted that he had met Keith at 2009's CMT Music Awards and appreciated "how awesome Toby was just as a human and how Toby made him feel comfortable and was cracking him up before they went out."

This article originally appeared on Nashville Tennessean: Stagecoach 2024: Jelly Roll, T-Pain pair for cover of Toby Keith song