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    Home » News » WATCH: T-Pain & Jelly Roll Honor Toby Keith With Performance Of “Should’ve Been a Cowboy” At Stagecoach

    WATCH: T-Pain & Jelly Roll Honor Toby Keith With Performance Of “Should’ve Been a Cowboy” At Stagecoach

    Brady GrayBy Brady GrayApril 27, 2024 Entertainment
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    T-Pain, Jelly Roll
    TikTok: @laurennnhoward
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    Didn’t have this performance on my bingo card for 2024…

    Ever since Toby Keith passed away back in early February, celebrities and musicians from all genres and walks of life have spoken out, mourning the loss of the country music legend. From nearly everyone in the country music community (other than the Dixie Chicks), and even late night talk show host, Stephen Colbert, it seems as if Toby’s music touched the lives of many over the last three decades.

    The latest artist to pay tribute to Toby, however, is not one that I would’ve expected. Although he’s dabbled in country music before (absolutely crushing his cover of ‘Tennessee Whiskey), T-Pain singing “Should’ve Been a Cowboy” in 2024 just shows you we are living in a simulation. Regardless, the hip-hop icon teamed up with rapper-turned-country artist, Jelly Roll, at Stagecoach last night and actually delivered a pretty cool tribute performance.

    Check it out here:

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    jelly roll T-Pain toby keith
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    We Asked Country Music Fans For Their Favorite Forgotten Songs And Their Answers Did Not Disappoint

    January 26, 2026

    Is Morgan Wallen a Pop Star? Breaking Down the Debate After Billboard Places Him In Their Top Ten Pop Stars Of 2025 List

    January 26, 2026

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    January 26, 2026

    “What Is Happening??” – Eric Church, Morgan Wallen, HARDY and Tim McGraw Have Fans Freaking Out After Sharing Cryptic Posts To Social Media

    January 26, 2026

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