4 “Should’ve Been a Cowboy” Covers That Actually Do Toby Keith Justice

Beloved country music star Toby Keith passed away back in February of 2024, and the tributes have been pouring in since his tragic death. One of his biggest hits, “Should’ve Been A Cowboy”, is just one of many songs that have been covered by other artists since his passing. Let’s look at some of the best covers of “Should’ve Been A Cowboy” in honor of the late singer/songwriter.

Videos by American Songwriter

1. Carrie Underwood

Carrie Underwood can cover virtually any song and make it sound fantastic. Her cover of the Toby Keith classic was just as incredible as you’d expect. The live cover took place on April 13, 2024 at the Grand Ole Opry in honor of Keith.

2. Jelly Roll & T-Pain

Country star Jelly Roll is famously a huge fan of Toby Keith and has said that his music inspired him throughout his own career. 

“Toby inspired millions and I was one of them,” Jelly Roll said on Instagram. “RIP.”

Shortly after Keith’s passing, Jelly Roll covered the track during a stop on his 2023 Backroad Baptism Tour. Just recently, the star dropped an official recorded cover via Amazon Music with some help from producer and fellow artist T-Pain. It’s one hell of a cover, and you can tell that Jelly Roll really admired Keith.

[Get Tickets To See Jelly Roll Live In 2024]

3. Brooks & Dunn

Brooks & Dunn and Toby Keith had their own respective career peaks around the same time, so it makes sense why the former would cover the latter posthumously. At the 2024 CMT Music Awards, Brooks & Dunn busted out this killer cover of the Toby Keith original against images of the late country star in the background.

4. Luke Combs

@lukecombs

Played the Ryman in Nashville this week so I couldn’t pass up the opportunity to honor a true icon. Thank you for everything, Toby. We’ll miss you.

♬ original sound – Luke Combs

Shortly after Keith’s passing, Luke Combs covered the iconic track during his performance at Ryman Auditorium in Nashville. His rendition was much more intimate than many on this list, as he played to a smaller crowd. His cover was excellent, though what else would you expect from someone who breathed new life into Tracy Chapman’s “Fast Car”?

“Played the Ryman in Nashville this week so I couldn’t pass up the opportunity to honor a true icon,” said Combs on social media. “Thank you for everything, Toby. We’ll miss you.”

Photo by Matt Winkelmeyer

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