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.


Lauren Jo Black

| Posted on

April 28, 2024


6:29 pm

Share on:

T. Pain with Jelly Roll at Stagecoach 2024

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. 

Jelly Roll performing at Stagecoach 2024
Jelly Roll; Photo by M McDonald for Stagecoach

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.

Share on:

Lauren Jo Black

Written by

Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for and her work being featured on She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.