Last night (April 26), 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.”
“Should’ve Been a Cowboy” was Toby Keith’s introduction to the country music world. It was the lead single from his debut album. The single went to No. 1 on the country singles chart, dominated the airwaves, and cemented Keith as a hitmaker and force to be reckoned with. Later, it became his signature song. As a result, it was the best way for Jelly Roll to honor one of his musical heroes on the Stagecoach stage.
Videos by American Songwriter
[RELATED: Jelly Roll Opens Up About Covering Toby Keith’s “Should’ve Been a Cowboy” with T-Pain]
Jelly Roll and T-Pain also released a recorded version “Should’ve Been a Cowboy.” However, fans will only be able to hear it if they buy the single from Amazon Music. The money goes to a good cause, though. All of the proceeds from sales of the song will go to benefit the Toby Keith Foundation which helps fund treatment for pediatric cancer patients and housing for their families during treatment.
Jelly Roll on Why He Covered “Should’ve Been a Cowboy”
In a recent interview with Variety, Jelly Roll said that he started covering “Should’ve Been a Cowboy” almost a year before Keith passed away. He did so because he loved the song and, more importantly, because he looked up to Keith.
“Toby Keith was one of the artists that—from afar, even though he would never have known it—encouraged me to do country music,” he revealed. “Just the whole way he put his personality into his music. He was an outlier. He was unapologetically Oklahoma,” Jelly added. “There are a lot of things that he did that encouraged me and empowered me. He never knew it but he was a mentor to me, just watching him from afar.”
Featured Image by Amy Sussman/Getty Images for Stagecoach
More Latest Music News & Stories
-
BIRMINGHAM, ENGLAND – JULY 29: Tony Iommi and his band (L-R) Mike Exeter, Karl Brazil, Becky Baldwin and Jørn Lande, pose during the launch of his new album "From The Dark" on July 29, 2026 in Birmingham, England. (Photo by Katja Ogrin/Getty Images) -
INDIO, CALIFORNIA – APRIL 27: (FOR EDITORIAL USE ONLY) Garth Brooks performs with Luke Combs at the T-Mobile Mane Stage during the 2025 Stagecoach Festival on April 27, 2025 in Indio, California. (Photo by Frazer Harrison/Getty Images for Stagecoach) -
US country singer Luke Combs performs at the Johan Cruijff ArenA in Amsterdam on July 11, 2026 as part of his world tour My Kinda Saturday Night. (Photo by Dingena Mol / ANP / AFP via Getty Images) / Netherlands OUT -
Photo by: Trae Patton/NBC via Getty Images -
NASHVILLE, TENNESSEE – NOVEMBER 08: EDITORIAL USE ONLY Chris Stapleton performs onstage during the 57th Annual CMA Awards at Bridgestone Arena on November 08, 2023 in Nashville, Tennessee. (Photo by Astrida Valigorsky/WireImage) -
Photo by NDZ/Star Max/GC Images -
INDIANAPOLIS, INDIANA – APRIL 04: Zac Brown of Zac Brown Band performs onstage for Coca-Cola Live! during the 2026 NCAA March Madness Music Festival on April 04, 2026 in Indianapolis, Indiana. (Photo by Marcus Ingram/Getty Images for TNT Sports) -
CMA FEST PRESENTED BY SOFI – Hosted by multi-award-winning country star Riley Green and Emmy Award-winning anchor and host from ABC's "Good Morning America" Lara Spencer, "CMA Fest presented by SoFi" is a three-hour concert event, filmed during the 53rd CMA Fest in downtown Nashville. This special airs Thursday, June 25, at 8/7c on ABC and streams the next day on Hulu. (Disney/Connie Chornuk)TIM MCGRAW (Photo by Connie Chornuk/Disney via Getty Images)