Jelly Roll cover 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 night on the opening day of the country music festival on Friday (April 26), the “Need a Favor” singer welcomed several unexpected guests to 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, California, shortly before Eric Church's headlining slot.

Halfway through his 50-minute set, it was Jelly Roll with 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 on Amazon Music a day earlier. The country star shared his thoughts on the classic track leading up to the music festival.

“I've been covering 'Should've Been a Cowboy' for about a year now at most of my shows, just honoring Toby as he was getting sick before he died,” Jelly Roll he said Variety. “That's when I really got down to it, man, what better place to honor Toby than Stagecoach? Plus, Toby Keith was one of the artists who, from afar, even though he would never have known it, encouraged me to get into country music.”

Funds raised from the 'Should've Been a Cowboy' cover will go to the Toby Keith Foundation, which helps pediatric cancer patients. Keith died earlier this year after a battle with stomach cancer.

Elsewhere during his Stagecoach set, Jelly Roll welcomed partner Ernest for a performance of 'Son of a Sinner', which reached No.1 in Advertising signof the Country Airplay chart in 2022. Jelly Roll was also along with Maddie & Tae in what he titled a brand new song titled “Liar.” The country duo will perform their own set on Saturday, April 27.

Jelly Roll finished his performance by bringing out his wife, Bunnie XO, and his daughter, Bailee Ann, turns 16. To celebrate her birthday next week, the country star asked her thousands of fans to sing happy birthday with him.

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

Stagecoach continues with starring performances from Miranda Lambert and Morgan Wallen, as well as sets from 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 are speculating that Beyoncé could make a surprise appearance at Stagecoach under the name “DJ Backwoods Barbie,” an unknown performer on the roster. Backwoods Barbie is the name of a Dolly Parton album and Bey collaborated with Parton on Cowboy Carter.