Jelly Roll Covers Toby Keith’s Classic “Should’ve Been A Cowboy”

(Background Photo) @rachalfam / Instagram (Circle Photo) Toby Keith / Instagram

Jelly Roll has been performing Toby Keith’s legendary “Should’ve Been A Cowboy” for quite some time, featuring it prominently in his previous live shows.

The significance of covering this beloved country tune has deepened profoundly for the singer since the tragic passing of Toby Keith on Monday, February 5, marking a heartbreaking moment for both country music and the global community.

A fan shared a video capturing Jelly’ Roll’s performance of the ’90s hit during one of his stops on the 2023 Backroad Baptism Tour. 

His rendition mirrored the original with remarkable accuracy. Jelly Roll infused the song with the same raw vocal intensity and vibrant energy that characterized Keith’s version, showcasing his exceptional talent and deep connection to the song.

Jelly Roll’s rendition of Toby Keith’s timeless “Should’ve Been a Cowboy” stirred excitement among fans, who eagerly expressed their admiration through encouraging comments and glowing reviews.

“Nice job Jelly Roll and Toby would be proud!!! Rest easy cowboy!!!!”

“Great song Great Job Making Toby proud”

“Jelly Roll sounds so good!”

“Bro should record that”

Following the footsteps of numerous country music artists, icons, and admirers, Jelly Roll took to social media to pay tribute to Toby Keith.

“We covered ‘Should’ve Been a Cowboy’ at every show last year,” Jelly Roll wrote in his tribute posted to his Instagram story. “Toby inspired millions and I was one of them. RIP.”

Jelly Roll pays tribute to Toby Keith.
Courtesy of Entertainment Tonight via Jelly Roll / Instagram

The country music world is rallying together to honor the late Toby Keith, with artists from various backgrounds finding inspiration in his legacy.

RELATED: Reba McEntire Mourns Toby Keith’s Death


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A post shared by Carrie Underwood (@carrieunderwood)

RELATED: Carrie Underwood Honors Toby Keith In Powerful Tribute


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A post shared by Dolly Parton (@dollyparton)

With Toby Keith’s untimely passing, it’s likely that Jelly Roll will continue to perform “Should’ve Been A Cowboy” at his future concerts.

Listen to Jelly Roll sing “Should’ve Been A Cowboy” below.