Jelly Roll is carrying on the legacy of country legend Toby Keith, and he did so in grand style as he welcomed 2025. The 40-year-old country star made sure that Keith’s influence was felt on Nashville’s biggest stage during the New Year’s Eve celebration at Bicentennial Park. With his five-song performance, Jelly Roll closed out the night by performing a powerful cover of Keith’s iconic hit, “Should’ve Been a Cowboy,” a song that has become symbolic of the late singer’s trailblazing career.
Toby Keith, who passed away at 62 in February 2024 following a battle with stomach cancer, left behind a legacy that continues to inspire. Since Keith’s passing, Jelly Roll has paid tribute to the late star several times, but this performance was especially poignant, taking place in Keith’s home state of Tennessee during one of the most significant events of the year.
Jelly Roll’s tribute at the Big Bash came after an emotionally charged set that included his own hits such as “I Am Not Okay,” “Need a Favor,” “Son of a Sinner,” and “Liar.” But it was his rendition of “Should’ve Been a Cowboy” that brought the night full circle. The crowd, familiar with Jelly Roll’s powerful delivery and emotion-filled performances, embraced the tribute to Keith with a deep sense of respect and admiration.
In addition to the song, Jelly Roll’s presence at the event underscored the bonds in the country music community. The New Year’s Eve special was packed with a star-studded lineup, featuring country heavyweights like Keith Urban, Kane Brown, Luke Bryan, Miranda Lambert, and Eric Church, along with crossover artists like Post Malone and Chris Stapleton.
This wasn’t the first time Jelly Roll had performed the song in Keith’s honor. In April 2024, Jelly teamed up with hip-hop artist T-Pain to cover “Should’ve Been a Cowboy” at the Stagecoach festival in Indio, California. Their collaboration was such a hit that it was released as an exclusive on Amazon Music. The performance garnered attention not only for its nostalgic tribute to Keith but also for the fusion of country and hip-hop—a signature moment of Jelly Roll’s unique style.
Jelly Roll has long credited Toby Keith as a major influence on his musical journey. In an interview with Variety, the country star revealed that it was Keith’s unapologetic approach to country music, and his ability to carve his own path, that inspired Jelly Roll to make the shift from rap to country music.
“He was an outlier. He was unapologetically Oklahoma,” Jelly Roll said. “There are a lot of things he did that encouraged me and empowered me. He was very individualistic and carved his own path and he did it his own way, from pillar to post. He never knew it, but he was a mentor to me, just watching him from afar.”
As a tribute to Keith, Jelly Roll reached out to Toby’s son, Stelen, before releasing the cover with T-Pain. Stelen, who had seen a video of Jelly performing the song, offered his blessing. “He took me to the side at the CMTs and said, ‘I’ve seen a video of you covering this song, and I think it’s one of the best versions of it ever. I think you honor my father,'” Jelly shared. “That meant so much to me.”
The emotional tribute didn’t stop at the performance. Jelly Roll and T-Pain made the decision to donate the proceeds from their cover of “Should’ve Been a Cowboy” to the Toby Keith Foundation, a cause close to Keith’s heart. The gesture was a heartfelt way of keeping Keith’s legacy alive while also giving back to the community.
T-Pain, who was a close friend of Keith’s, explained the significance of their collaboration, revealing a personal anecdote about the late singer. “The only time I’ve ever done something big in the country space, at the CMT Awards, I presented with Toby in 2009,” T-Pain shared. “He was just such an awesome human. He made me feel comfortable, cracked me up before we went out. He made me feel like I belonged.”
Together, Jelly Roll and T-Pain chose to donate the proceeds from their cover to the Toby Keith Foundation, ensuring that Keith’s charitable efforts continue to make a difference.
Jelly Roll’s tribute to Toby Keith on New Year’s Eve was a reflection of the deep respect he has for the country legend. As Jelly Roll continues to rise in the country music ranks, his journey is intertwined with the paths blazed by artists like Toby Keith, whose authenticity and groundbreaking approach to music continue to inspire future generations.
In 2025, Jelly Roll is not just a rising star in country music, but a keeper of the legacy of those who paved the way. His tribute to Toby Keith is a testament to his respect for the legends before him and his determination to carry their torch forward.
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