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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 Country Music
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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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    Morgan Wallen Snatches Phone From Security Guard’s Hand And Chucks It Across The Stage At Pittsburgh Show [Watch]

    June 6, 2026

    Megan Moroney’s Setlist For Her 2026 ‘Cloud 9’ Tour Revealed

    May 30, 2026

    Country Singer’s Wife Accuses Riley Green Of Stealing Lyrics From Her Husband’s Song In “Think As You Drunk” And Then Claims She Was Blocked After Calling Him Out

    May 29, 2026

    Jamey Johnson Pays Tribute To Legendary Songwriters Don Schlitz And Paul Overstreet With Incredible Performance Of Keith Whitley’s “When You Say Nothing At All” At The Grand Ole Opry

    May 29, 2026

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