Pain "would be a perfect surprise guest for Stagecoach that nobody would see coming" in an interview before his performance at the music festivalJelly Roll used his 2024 Stagecoach set to honor the late Toby Keith — with a little help from T-Pain.

Stagecoach Country Music Festival, a stage known for memorable performances, Jelly Roll captivated the audience with a poignant dedication to Toby Keith, with T-Pain unexpectedly joining him for a poignant musical tribute.

Toby Keith, the late country music legend, to be honored posthumously with a degree from the University of Oklahoma, alongside other esteemed recipients.

The Opry performance isn't the only time the "Out of That Truck" hitmaker has taken on the wildly popular song: Underwood sang "Should've Been a Cowboy" during the 2022 BMI Country Awards when Keith was recognized as a BMI Icon.

Jelly Roll recorded his own version of Toby Keith’s first #1 song, “Should’ve Been a Cowboy.” The track features vocals from hip-hop artist, T-Pain. It was released a couple of hours before their Stagecoach performance on Friday as part of the Amazon Music Originals.

Pain, Ernest, Maddie & Tae, wife and daughter in wide-ranging Stagecoach set that was equal parts poignant and party

Jelly Roll made his Stagecoach Festival debut in style. He invited several guests to join him on the stage. However, for many, the highlight of his set was when he brought T-Pain out for their cover of Toby Keith’s signature hit “Should’ve Been a Cowboy.