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    Country Chord – Country Music News and EntertainmentCountry Chord – Country Music News and Entertainment
    Home » News » WATCH: Riley Green Delivers Exceptional Cover of “Should’ve Been A Cowboy” by Toby Keith

    WATCH: Riley Green Delivers Exceptional Cover of “Should’ve Been A Cowboy” by Toby Keith

    Clayton AndersonBy Clayton AndersonFebruary 6, 2024 Country Music
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    Timeless.

    Riley Green is no stranger to covering 90’s classics. From Sammy Kershaw’s “The Yard,” to Rhett Akins’ “That Ain’t My Truck,” the country superstar consistently pays homage to the legends before him.

    Just recently Riley Green, sportin’ a dark tan cowboy hat, covered Toby Keith’s 1993 classic, “Should’ve Been A Cowboy” and the fans in attendance LOVED it.

    Cowboy was written solely by Keith and was his first ever single released to Country radio off his debut self-titled album.The track ended up going #1 just four months after its release and also peaked at #93 on the Billboard Hot 100 chart, making it a minor crossover hit.

    With over 2 dozen #1 hits across three decades and 40 million albums sold, the 62 year-old singer/songwriter has quietly, yet consistently, made himself one of the biggest names in all of country music.

    Toby recently made a surprise performance alongside Jason Aldean in Oklahoma City just four months before his death to perform Should’ve Been A Cowboy. You can watch that here.

    Riley Green also recently released his sophomore studio album, “Ain’t My Last Rodeo,” and it features a cover of Tim McGraw’s “Damn Country Music,” as well as his recent single, “Different ‘Round Here,” a re-release off his 2019 debut album of the same title, that now features Luke Combs.

    Rest easy, Toby.

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    Kaitlin Butts Returns To Acting In Mini-Musical For New Album ‘Hello, Honky Tonk’ Featuring Lainey Wilson As A Talking Deer

    November 11, 2026

    Stephen Wilson Jr. Performs Stunning Rendition Of “Stand By Me” During Couple’s First Dance: “I Would Divorce My Wife & Get Remarried Just To Have Him Play”

    November 11, 2026

    To Every Fan Who Stood Up, Every Artist Who Spoke Up… I Want To Thank You” – Sammy Kershaw Says He Will Now Attend CMA Awards After “Heartfelt Apology”

    November 10, 2026

    Ronnie Dunn Reflects On Brooks & Dunn Opening For Morgan Wallen: “At First It Was Uncomfortable…We’re Used To Headlining”

    November 10, 2026

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