Luke Bryan Shares Emotional Story Behind Cowboy Hat Worn For Toby Keith Tribute

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On Monday night (July 29), Music City held a star-studded tribute concert to honor the late Toby Keith, called Toby Keith: American Icon.

Thousands of fans and country music’s top artists filled the Bridgestone Arena in Nashville to celebrate Toby Keith’s legacy. The two-hour event featured powerful performances of his greatest hits and appearances from many of his closest friends.

Toby Keith: American Icon will be broadcast on NBC on August 28.

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Among the standout performers of the night was Luke Bryan, who had the privilege of singing Toby Keith’s beloved anthem, “Should’ve Been A Cowboy.” Released in 1993, the song was Toby’s debut single and secured him his first number one hit.

While Bryan has often covered this song and other Toby Keith hits in his concerts since Toby’s passing in February, this particular performance felt especially meaningful.

You can watch part of Bryan’s “Should’ve Been A Cowboy” performance below.

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Update: Luke Bryan covers “Should’ve Been A Cowboy” by Toby Keith at Bridgestone Arena in Nashville, TN #lukebryan

♬ original sound – Up2Date Country

Other touching tributes during the concert came from Carrie Underwood, Darius Rucker, Ashley McBryde, and MANY more!

During his performance, Luke Bryan wore a black cowboy hat. This was a rare choice for him as he typically opts for a simple baseball cap. It turns out, there was a very special meaning behind why he chose to wear it.

Before launching into the iconic song, Bryan took a moment to address the crowd, expressing that it was an “honor” to be part of the event.

He shared a few stories about his friendship with Toby, reminiscing about Toby’s knack for humor and his endless supply of new songs. Then, Bryan surprised the audience by pausing to grab a cowboy hat that was hanging behind him.

He told the audience the significant meaning behind the hat:

“So this hat has been hanging in my closet for probably fifteen years. My sister down in Georgia, when I was playing bars and doing about ten Toby Keith songs a night, my sister bought me this hat. I used to wear this hat every night. Ever since I lost my sister, I haven’t put this hat on stage in a lot of years. I was walkin’ out the house and I said, ‘You know what? I’m just an ol’ country boy from Georgia, but Toby Keith certainly made me wanna be a cowboy…This is for you Toby!”

What a special way to honor both Toby and his sister! Listen to his speech and watch his full performance in the video below.