Jelly Roll Couldn’t Get Toby Keith off His Mind—so He Honored “One of the Greatest Cowboys” With a Memorable Cover

When you produce 20 No. 1 hits, you have to be selective about which ones you play during a two-hour live show. It’s a good problem to have, and Toby Keith had it. But the late country artist always had time for his chart-topping debut single, “Should’ve Been a Cowboy.” March 5 marked a month since Toby Keith died at age 62 after a debilitating battle with stomach cancer. The singer-songwriter inspired millions, including Best New Artist nominee Jelly Roll. This week, country’s brightest new star used his Houston Rodeo set to pay tribute to Keith.

Videos by American Songwriter

[RELATED: Riley Green, Tracy Lawrence, & Ella Langley Pay Tribute to Toby Keith With “Should’ve Been a Cowboy” Cover]

Jelly Roll Covers ‘Should’ve Been a Cowboy’

The “Son of a Sinner” singer made his Houston Rodeo debut Wednesday night (March 6.) Jelly Roll (born Jason DeFord) took a moment to honor all the country music heavyweights who’d graced the same stage before him at NRG Stadium.

“I could only think of one person when I pulled up to NRG tonight,” the Antioch, Tennessee native said. “And it made me think of one of the greatest cowboys that ever lived, and I said, ‘We’re gonna honor him.'”

The fan behind the camera didn’t need to hear Jelly Roll say any names. They exclaimed, “Toby Keith!” as soon as “cowboy” left the singer’s mouth.

Approximately 73,000 voices joined in as Jelly Roll sang, “I should’ve been a cowboy / I should’ve learned to rope and ride.”

“Rest in peace, Toby Keith!” the “Need a Favor” artist shouted over thunderous applause. “We love you!”

All The Times Toby Keith Performed at the Houston Rodeo

Despite hailing from the wrong side of the Red River, Keith could always count on a warm welcome from the Bayou City’s rodeo-goers.

The native Oklahoman performed at the Houston Rodeo nine times, with the last time coming in 2013.

The month since Keith’s passing has at times felt like one never-ending tribute to the “Red Solo Cup” singer. Everyone from Post Malone to Carrie Underwood had something to say about Keith’s impact.

“Saddle up the horses, Jesus, ‘cause a true blue COWBOY just made his ride up to heaven!!!”” Underwood wrote on Instagram after Keith’s death was announced. “Introduce him to all the Okies and sign that boy up for the choir!”

Featured image by Unique Nicole/Getty Images for The Recording Academy

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