Country music star Jelly Roll, 40, paid tribute to the late Toby Keith during Nashville’s Big Bash New Year’s Eve celebration. Closing his five-song set at Tennessee’s Bicentennial Capitol Mall State Park on December 31st, Jelly Roll performed a heartfelt rendition of Keith’s iconic hit, “Should’ve Been a Cowboy.”
Keith, who passed away in February 2024 at age 62 after battling stomach cancer, has been honored by Jelly Roll with performances of “Should’ve Been a Cowboy” on multiple occasions. The New Year’s Eve performance followed Jelly Roll’s own hits, including “I Am Not Okay,” “Need a Favor,” “Son of a Sinner,” and “Liar.”
The star-studded Nashville’s Big Bash also featured performances from country music giants like Keith Urban, Kane Brown, Luke Bryan, Luke Combs, Eric Church, Tyler Hubbard, Miranda Lambert, Brittney Spencer, Chris Stapleton, and Lainey Wilson. Other notable performers included Shaboozey, Post Malone, and Zach Top.
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This wasn’t Jelly Roll’s first time covering the classic country song. In April 2024, he teamed up with rapper T-Pain for a unique duet of “Should’ve Been a Cowboy” at the Stagecoach Festival in Indio, California. The collaboration, released exclusively on Amazon Music prior to the festival, garnered significant attention.
Jelly Roll has openly acknowledged Toby Keith’s influence on his musical journey, crediting Keith’s authenticity and individuality for inspiring his transition from rap to country music. In an interview with Variety, Jelly Roll described Keith as an outlier and a mentor, praising his independent spirit and unwavering commitment to his own style. Songs like “Should’ve Been a Cowboy,” “The Next Thing on My List,” and “I Love This Bar” played a pivotal role in shaping Jelly Roll’s artistic direction.
Before releasing the cover with T-Pain, Jelly Roll sought and received the blessing of Keith’s son, Stelen. Stelen expressed his admiration for Jelly Roll’s rendition of the song, calling it one of the best versions he had ever heard and a true honor to his father’s legacy.
The collaboration with T-Pain was particularly meaningful due to the rapper’s personal connection to Toby Keith. T-Pain shared a story with Jelly Roll about a memorable encounter with Keith at the 2009 CMT Awards, highlighting Keith’s kindness and humor.
Inspired by Keith’s philanthropic spirit, Jelly Roll and T-Pain decided to donate the proceeds from their cover of “Should’ve Been a Cowboy” to the Toby Keith Foundation, further cementing their tribute to the country music legend.
