Jelly Roll Sings Toby Keith’s ‘Should’ve Been A Cowboy’

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Country Music News, Jelly Roll, News, Toby Keith
Mandy Robinson

Jelly Roll has been doing a cover of Toby Keith’s “Should’ve Been A Cowboy” for quite some time now, including it in his past concerts. Covering that great country song has taken on new meaning to the “I Need A Favor” singer since last Monday, February 5th. That was the day country music and the rest of the world lost Toby Keith.

Jelly Roll Has Always Been A Fan Of Toby Keith

Jelly Roll is not the least bit shy about admitting he has always been a fan of the “Courtesy Of The Red, White And Blue” singer. He has included “Should’ve Been A Cowboy” in all of his concerts last year.

Jelly Roll is not just a fan of Toby Keith. He sees Keith as an “inspiration.” According to Jelly Roll, he didn’t just inspire him, but “millions” of others as well.


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Jelly Roll Posts Tribute To Toby Keith On Instagram

Like so many other country music singers, superstars and fans, Jelly took to social media to honor the late Toby Keith. Jelly Roll chose Instagram to express his sorrow over Keith’s passing.

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

With the sudden and untimely passing of Toby Keith, it is easy to think he will continue to sing “Should’ve Been A Cowboy” during his future concerts. It would give the “Son Of A Sinner” singer even more opportunities to honor the country music star who inspired him.


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Toby Keith’s Death

Toby Keith passed away suddenly on Monday, February 5, 2024. He was at his home in Oklahoma. His family shared this shocking and sad news on social media. According to the post Keith’s family made, Toby Keith passed away in his sleep, surrounded by his family.

Toby Keith had been battling stomach cancer. Even after undergoing chemotherapy, radiation and at least once surgery, the “How Do You Like Me Now” singer lost his battle with stomach cancer. Tributes to Toby Keith began pouring in from social media from country music singers and fans from all over the globe.Those tributes continue to be posted on social media.

Tell us what you think. Have you heard Jelly Roll sing “Should’ve Been A Cowboy?” If so, what did you think of his rendition of Toby Keith’s hit song? Were you shocked by Keith’s death? Like so many other people, did you post a tribute to the “American Made” singer? Please feel free to share your thoughts and feelings in the comment section below.

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