Toby Keith and Blake Shelton Sing ‘Should’ve Been a Cowboy’ at 2018 ACM Awards

Two Oklahoma natives, Toby Keith and Blake Shelton, took the stage in Las Vegas, Nev., at the 2018 ACM Awards on Sunday night (April 15), to perform Keith's 1993 hit "Should've Been a Cowboy." The duet was one of three "ACM Flashbacks" pairings scheduled for the night.

Shelton took the stage to introduce Keith before their performance, and when the camera panned to the 56-year-old, he started the set holding up a red Solo cup. The two singers stood side by side with their acoustic guitars, and everyone in the crowd sang along and danced to the familiar song. At the end, Keith once again raised his cup to the audience.

"Should've Been a Cowboy" was Keith's debut single and was released 25 years ago, in 1993; the No. 1 hit became the most-played track of the 1990s on country radio. And Shelton is no stranger to hits himself: His single "I'll Name the Dogs" off his Texoma Shore album, was in the running for Single Record of the Year in 2018.

The "ACM Flashbacks" performances teamed up an iconic country singer and a modern hitmaker to honor a few of country music's greatest songs. Other performances set for the 2018 ACM Awards were Alan Jackson and Jon Pardi offering up their interpretation of Jackson's hit "Chattahoochee" and Reba McEntire and her daughter-in-law Kelly Clarkson singing "Does He Love You." All three songs are turning 25 years old in 2018.

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