Luke Bryan paid tribute to two of his late inspirations during NBC’s Toby Keith: American Icon special, which aired on August 28. Of course, he honored Toby Keith, who passed away in February 2024 after a battle with stomach cancer, and he also made a touching gesture for his late sister, Kelly, who passed away 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, Bryan pulled out a black cowboy hat for his performance and explained its significance to the audience. “This hat has been hanging in my closet for about 15 years,” he said. “My sister in Georgia bought me this hat when I was playing bars and doing about 10 Toby Keith songs a night. I wore this hat every night. Since I lost my sister, I haven’t worn this hat on stage in years.”

“I walked out of the house and I said, ‘You know what? I’m just an old country boy from Georgia. Toby Keith definitely made me want to be a cowboy. I’m going to 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 to almost all of his performances and public appearances. So Bryan wearing one was a tribute to Keith in and of 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 an amazing human being. Your songs make any room a good time.”

About Toby Keith’s “Should’ve Been a Cowboy.”

Keith wrote “Should’ve Been a Cowboy” himself and released it as his first-ever single in 1993. It evokes images of the Wild West, the fantasy of the exciting cowboy lifestyle and references to both fictional and historical cowboys. “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 sitting in the back of the bus with (then-touring partner) Shania Twain,” Keith recalled at a 2007 event in Nashville, according to Yahoo!. “Those are fond memories. We left Nashville as a couple of rookies and went to Kentucky and turned on the radio. ‘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 WOW

Watch Toby Keith: American Icon on NBC on Wednesday, August 28 at 9:00 p.m. ET/PT. Other performers include Carrie Underwood and Lainey Wilson.