Jelly Roll Joins Forces With T-Pain For Surprise Toby Keith Tribute At Stagecoach
“We wanted to stay as true to Toby and his memory and his honor as possible,” Jelly Roll shares.

T. Pain with Jelly Roll; Photo by J Bernstein for Stagecoach
Jelly Roll made his Stagecoach debut over the weekend and his performance was certainly one for the books with surprise special guests ERNEST, Maddie & Tae, and T-Pain.
Prior to taking the stage, the current ACM Entertainer of the Year nominee admitted, “I’m nervous, I’m excited, I’m all the emotions you could feel.”
Despite his nerves, the “Need A Favor” singer delivered a stellar Stagecoach debut, complete with his hits, a few covers, and more.

ERNEST joined the genre-bending star to perform the chart-topping hit “Son Of A Sinner,” while Maddie & Tae took the stage alongside the Nashville native to debut a new song called “Liar.”
One of the most talked about moments of the night was when Jelly Roll joined forces with the hip-hop legend T-Pain to honor the late Toby Keith with a performance of Keith’s iconic hit, “Should’ve Been A Cowboy.” Together, they tipped their hats to the soon-to-be Country Music Hall of Famer as the crowd sang along to every word.
@laurennnhoward Day 1 Stagecoach 2024 🇺🇸❤️ #stagecoach #palmsprings #countrymusic #america #fy #fyp #tpain #jellyroll ♬ original sound – Lauren Howard
Jelly Roll has been performing this song during his live show for quite some time and recently teamed up with T-Pain to record the song for an Amazon Music Original cover.
“We wanted to stay as true to Toby and his memory and his honor as possible. Kind of the only reason we do the song at all is just to kind of memorialize Toby Keith and what he did for country music and all the music,” Jelly Roll explained of tribute during an interview with Amazon Music.
He went on to share how he got teamed up with T-Pain for the collab.
“We were looking for a good collaboration partner for this, especially to have a big Stagecoach moment as well. I thought about T-Pain when he took Stapleton’s Tennesee Whiskey and It was just so beautiful. He’s just got such an authentically soulful voice and as a Tallahassee boy, he’s definitely got that Southern drawl in him, so I thought it would sound really good,” the Nashville native stated.
Jelly Roll revealed that he is donating all proceeds from their cover of “Should’ve Been A Cowboy,” which is streaming exclusively on Amazon, to the Toby Keith Foundation, an organization that supports pediatric cancer patients.
During his set, Jelly Roll also welcomed his daughter, Bailee Ann, to the stage to sing her “Happy Birthday” amid the sea of country music fans.
Stagecoach, country music’s biggest festival, continues through Sunday evening. Throughout the weekend fans were able to enjoy performances by Eric Church, Miranda Lambert, Willie Nelson & Family, HARDY, Post Malone, Zach Top, Tenille Townes, Tanner Adell, and so many more.
The festival is set to close out with a performance from Morgan Wallen.
Lauren Jo Black is a longtime country music journalist, editor, host, and media personality whose work has helped shape the conversation around country music for nearly two decades. As the current Editor-in-Chief of Country Now, she has become one of the genre’s most respected voices, interviewing hundreds of country music’s biggest stars, including Dolly Parton, Garth Brooks, Reba McEntire, Shania Twain, Randy Travis, Luke Bryan, Carrie Underwood, Blake Shelton, Luke Combs, and countless others. Over the course of her career, Black’s written work and interviews have reached billions of country music fans worldwide. A 2009 graduate of the University of Central Florida, Black began her career by founding Country Music Is Love, one of country music’s earliest independent digital publications, which she later sold to a major record label in 2015 before it was rebranded as Sounds Like Nashville. She then served as the publication’s Editor-in-Chief for more than two years. Her work has also appeared in Forbes, and she previously served as the Country Music Expert for Answers.com. Widely recognized for her expertise, Black has appeared as a featured guest on The Bobby Bones Show, BobbyCast, and Scripps News Morning Rush, providing insight on country music’s biggest moments. She has also hosted Country Now Live, a concert series featuring performances from artists including Lady A, Dierks Bentley, Riley Green, Jordan Davis, Dustin Lynch, Gabby Barrett, Brett Young, Jon Pardi, Kip Moore, Chris Young, and more. The series has welcomed thousands of fans in person while reaching millions more online. In addition, she hosted Connect With Country Now, a weekly interview series featuring conversations with rising country stars. Throughout her career, Black has earned a reputation for discovering and championing artists long before they become household names. She has covered Luke Bryan since the early days of his career, beginning when he was writing songs for other artists, including Billy Currington’s No. 1 hit “Good Directions,” before stepping into the spotlight with his debut single, “All My Friends Say” and eventually becoming one of biggest names in music. She also gave Megan Moroney her first opportunity to walk a major red carpet as Country Now’s official guest correspondent at the 2022 CMA Awards. An interview she conducted in 2018 for Forbes.com with Luke Combs that inspired his multi-week No. 1 hit, “Doin’ This.” She has also hosted stages at CMA Fest, moderated an industry panel at Country Radio Seminar, and helped lead important conversations about the evolving landscape of country music media. Beyond journalism, Black has also used her platform to support charitable causes and highlight organizations making an impact. Through Country Now Live, she has helped raise awareness and support for St. Jude Children’s Research Hospital, while also advocating for animal rescue through Country Now’s Pupdate series, spotlighting organizations including MuttNation Foundation, Wags & Walks, and Proverbs 12:10 Animal Rescue. Black has been recognized as one of Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. She is a longtime member of both the Country Music Association (CMA) and the Academy of Country Music (ACM). After nearly 20 years covering country music, Lauren Jo Black has spent her career telling the stories behind the artists, songs, and moments that have shaped the genre. Her first-ever book, Country Music Forever: An A-to-Z Celebration of Icons, Songs and Stories, brings that same passion and firsthand knowledge to the page, celebrating not only the legendary artists and timeless songs that have become the soundtrack to generations of fans, but also the places, traditions, and cultural moments that have made country music one of the most beloved genres around the world.







