Riley Green and Randy Houser Deliver Emotional Tribute to Toby Keith With Surprise Duet of “Should’ve Been A Cowboy” at Sand In My Boots Festival

Sand In My Boots Festival Draws 40,000 Country Fans to Gulf Shores

From May 16–18, the Sand In My Boots festival made a thunderous debut in Gulf Shores, Alabama, drawing nearly 40,000 passionate country music fans. Spearheaded by CMA Entertainer of the Year Morgan Wallen, the sold-out, three-day event featured an all-star lineup across multiple genres, making it one of the most anticipated new festivals of 2025.

The lineup included country powerhouses like Riley Green, Brooks & Dunn, HARDY, and even crossover superstar Post Malone. Morgan Wallen himself closed out the weekend on Sunday night with a show-stopping headlining set, perfectly timed with the release of his massive 37-track album, I’m The Problem, which dropped on May 17.

Riley Green Rocks the Stage With Hit-Filled Set and a Surprise Appearance by Randy Houser

 

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On Saturday, May 17, Riley Green took over the main stage and lit up the night with a dynamic performance of fan favorites, including his chart-topping duet with Ella Langley, “You Look Like You Love Me.”

But the night’s most unforgettable moment came when Randy Houser made a surprise entrance. The two artists delivered a powerful duet of “Should’ve Been A Cowboy” in honor of the late Toby Keith—a moment that brought the crowd to their feet in a wave of cheers and emotion.

A Timeless Tribute to a Country Legend

 

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Originally released in 1993, “Should’ve Been A Cowboy” became Toby Keith’s breakout hit, soaring to No. 1 on the Billboard Country Chart and launching his storied career. Since Toby’s passing, the song has taken on new emotional weight, resonating even more deeply with fans across generations.

With this heartfelt duet, Riley Green and Randy Houser paid a fitting tribute to the country legend. Their performance not only honored Toby’s legacy but also brought thousands together in song and memory. As the crowd sang along to every word, the moment became a highlight of the festival—and a true celebration of country music’s enduring spirit.

Watch Riley Green and Randy Houser perform a duet of Toby Keith’s “Should’ve Been A Cowboy” at Sand In My Boots below! 

@natnine Should’ve Been a Cowboy | Riley Green & Randy Houser #SandInMyBoots #MissKitty #ShouldveBeenACowboy #Rodeo @Riley Green ♬ original sound – JustJames