Luke Bryan Delivers a Spirited Toby Keith Tribute Cover of “Should’ve Been a Cowboy”—and a Nod to His Late Sister

Toby Keith died in February after battling stomach cancer for more than two years. With a career spanning 30 years and 20 No. 1 hits, the “Beer For My Horses” singer’s life and legacy warrant one hell of a party. And that’s exactly what Nashville gave him with Toby Keith: An American Icon. Country star Luke Bryan took the stage at Bridgestone Arena for a heart-wrenching performance of Keith’s first hit.

Luke Bryan Honors Toby Keith, Late Sister With Moving Performance

“Should’ve Been a Cowboy” was Toby Keith’s ticket into the country mainstream. Released in 1993, the song skyrocketed to the top of the Billboard Hot Country Songs chart. Moreover, it established Keith as someone to watch in Nashville.

More than 30 years after its release, Luke Bryan honored his fellow country legend with his own spirited rendition of the 1993 hit.

The “Mind of a Country Boy” singer donned a special black cowboy hat for the occasion. He explained that it had been a gift from his sister back when “I was playing bars and doing about 10 Toby Keith songs a night.”

[RELATED: Toby Keith Tribute Concert Featuring Lainey Wilson, Jelly Roll, Luke Combs, and More Will Raise Money for Keith’s OK Kids Korral]

Bryan’s sister died in 2007, and the five-time Entertainer of the Year never wore the hat again—until now.

“Toby Keith certainly made me want to be a cowboy. So I’m gonna be a cowboy tonight,” said Bryan, 48, placing the hat on his head. “This is for you, Toby.”

“He Was Just a Bada–“

Toby Keith was a well-established staple of country music when Luke Bryan released his debut studio album in 2007. As the “Country Girl” singer grew his career, their paths crossed more and more often.

“I got to hang with Toby backstage at the Ryman a couple of years ago and tell some jokes. He always had the funniest jokes and the best stories,” Bryan told Country Now. “And he was a true country music personality. He walked in the room, you knew he was in the room.” 

Bryan went on to praise the “How Do You Like Me Now?!” singer’s unwavering devotion to the military.

“And I mean, listen, I know people that were on those trips and singing in the desert is not fun,” he said. “Toby was riding helicopters and doing multiple shows a day and he was just a bada–.”

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