Shelton and Keith have been friends in the music business for a long time. Both artists hail from the state of Oklahoma, their songs dominated the country charts throughout the 2000s and they’ve performed together on multiple occasions. Fans may remember when they took the stage at the 2018 ACM Awards for a performance of “Should’ve Been a Cowboy.”

Jason Kempin/ACMA2018/Getty Images

The two also joined Keith Urban and Dierks Bentley for a tribute to Glen Campbell at the ACM Honors in 2016. Watch below.

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Their friendship stood the test of time throughout the years, and in September 2023, it was Shelton who honored Keith with the Country Icon Award at the inaugural People’s Choice Country Awards. While presenting the award, Shelton recounted a conversation between himself and Keith when he was an opener on Keith’s tour in the early 200os.

“I was out there with Toby for a long time — almost two years I think — and I finally got to the point where I was comfortable enough being around him,” Shelton said. “I remember one night, it was after an awards show. Toby had been up for, like, four or five awards, and man, he didn’t win crap. I was talking to him after that, and I had the nerve, I was so excited to be able to get under his skin. I said, ‘Man, Toby. If I ever make it big enough one day, and I get nominated for some awards, I hope it’s against you.’”

Shelton also shared Keith’s quick retort to his comment.

“Toby looked at me, and he said, ‘You know why I brought you out on tour with me?’ I said, No,’” Shelton recalls. “He goes, ‘I wanted to prove to this industry that I don’t really need an opening act.’”

“I love my Oklahoma bother, everybody!” Shelton concluded.