Jelly Roll Covers Toby Keith’s ‘Should’ve Been a Cowboy’ With T-Pain at Stagecoach 2024

Jelly Roll was full of surprises at Stagecoach 2024.

During his wild evening set on the country music festival’s opening day Friday (April 26), the “Need a Favor” singer welcomed numerous unexpected guests onto the stage, including T-Pain, Ernest and Maddie & Tae.

Jelly Roll’s performance took place on the T-Mobile Mane Stage at Empire Polo Field in Indio, Calif., shortly before Eric Church’s headlining slot.

Halfway through his 50-minute set, Jelly Roll was joined by T-Pain for their cover of Toby Keith‘s hit song “Should’ve Been a Cowboy.” The pair dropped a recorded version of the cover for Amazon Music a day earlier. The country star shared his thoughts on the classic track leading up to the music fest.

“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,” Jelly Roll told Variety. “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.”

Funds raised from the “Should’ve Been a Cowboy” cover will go toward the Toby Keith Foundation, which aids pediatric cancer patients. Keith died earlier this year following a battle with stomach cancer.

Elsewhere during his Stagecoach set, Jelly Roll welcomed collaborator Ernest for a performance of “Son of a Sinner,” which reached No. 1 on Billboard‘s Country Airplay chart in 2022. Jelly Roll was also joined by Maddie & Tae on what he called a brand new song titled “Liar.” The country duo will perform their own set on Saturday (April 27).

Jelly Roll ended his performance by bringing out his wife, Bunnie XO, and daughter, Bailee Ann, is turning 16 years old. To celebrate her birthday next week, the country star asked the thousands of fans to join him in singing happy birthday.

Earlier in the day, Jelly Roll visited celebrity chef Guy Fieri at the Smokehouse Cooking Demo stage for a cooking lesson.

Stagecoach continues with headlining performances by Miranda Lambert and Morgan Wallen, as well as sets by Elle King, Post Malone, Willie Nelson, Hardy and Bailey Zimmerman, among many others. The festival is streaming live on Prime Video or Amazon Music’s Twitch channel.

Fans have been speculating that Beyoncé could be making a surprise appearance at Stagecoach under the name “DJ Backwoods Barbie,” an unknown performer listed on the roster. Backwoods Barbie happens to be the name of a Dolly Parton album and Bey collaborated with Parton on Cowboy Carter.