Luke Bryan’s Personal, Moving Cover of This Toby Keith Hit

Luke Bryan paid tribute to two of his late inspirations during NBC’s Toby Keith: American Icon special, airing August 28. Of course, he honored Toby Keith, who died in February 2024 after a battle with stomach cancer, and he also made a touching gesture to his late sister, Kelly, who died unexpectedly in 2007.

Luke Bryan’s very personal performance of “Should’ve Been a Cowboy” by Toby Keith

As you’ll see in the special, before starting his performance, Bryan picked up a black cowboy hat and explained its significance to the audience. “This hat has been hanging in my closet for probably 15 years,” he said. “My sister down in Georgia bought me this hat when I was playing bars and doing about 10 Toby Keith songs a night. I used to wear this hat every night. Ever since I lost my sister I haven’t put this hat on onstage in a lot of years.” 

“I was walking out the house, and I said, ‘You know what? I’m just an old country boy from Georgia. Toby Keith certainly made me wanna be a cowboy. I’m gonna be a cowboy tonight,'” Bryan continued before launching into Keith’s hit “Should’ve Been a Cowboy.” As fans know, Keith wore a cowboy hat during almost all his performances and public appearances. So Bryan wearing one was a tribute to Keith in itself. 

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When Keith passed away, Bryan wrote on Instagram, “Just…seeing the sad news in our country community. An iconic artist and a great man. Your songs turn every room into a good time.”

About “Should’ve Been a Cowboy” by Toby Keith

Keith wrote “Should’ve Been a Cowboy” by himself and released it as his very first single in 1993. It evokes the imagery of the Old West, the fantasy of the exciting cowboy lifestyle, and references to cowboys both fictional and historical. “Thirty-one years later…[the song] holds up,” Joseph Hudak wrote for Rolling Stone.

“The first time I heard it [on the radio], I was going to…Kentucky, and I was with [then touring partner] Shania Twain in the back of the bus,” Keith recalled at a Nashville event in 2007, per Yahoo!. “Those are good memories. We left Nashville as a bunch of greenhorns and went up into Kentucky and flipped the radio on. ‘Should’ve Been a Cowboy’ came on and it changed my life.” 

Carrie Underwood’s Electric Cover of Toby Keith’s “A Little Less Talk” Is W-O-W

Watch Toby Keith: American Icon on NBC on Wednesday, August 28 at 9 p.m. ET/PT. Additional performers include Carrie Underwood,and Lainey Wilson.