Carrie Underwood Honors The Late, Great Toby Keith With “Should’ve Been A Cowboy” At The Grand Ole Opry

Carrie Underwood country music
Grand Ole Opry

Carrie Underwood returned to the Grand Ole Opry last night, and during her set, took the time to honor a fellow Okie, the late, great Toby Keith.

Of course, Keith tragically passed away on February 5th from a 2-year battle with stomach cancer. The legendary singer had recently returned to the stage for 3 shows in Las Vegas, after giving his first televised performance since the diagnosis with his emotional performance of “Don’t Let The Old Man In” during the People’s Choice Country Awards last fall.

Carrie stepped into the iconic Opry circled and paid tribute the Big Dog Daddy with a cover of Keith’s 1993 hit single, “Should’ve Been A Cowboy.”

Released in February of 1993, “Should’ve Been A Cowboy” was Keith’s debut single, kicking off his illustrious career in country music. Peaking at #1 on the U.S. Billboard Hot Country Song chart, the song has more than three million spins on country radio too, which makes it the most-played country song of the 1990’s.

In an interview with Billboard in 2018, Keith shared a little bit of inspiration behind the song, which is an incredible story too:

“I think we were actually at the Long Branch Saloon or Miss Kitty’s Saloon — it was something to do with Gunsmoke. This highway patrolman who I had met on the trip, his name was John, he jumps up.

He was probably 45 or 50 back then, and he runs over to this 25-year-old cowgirl. He was going to show that he could bust a move. She turns him down. He comes over, and said, ‘She says she doesn’t dance.’

About 15 minutes later, a young cowboy comes in — and off they go on the dance floor. Everybody was making fun of him, and one of the guys said, ‘John, I guess you should have been a cowboy.’”

And the rest was history… RIP Toby.

Following her performance, Carrie thanked the Opry and the city of Nashville for the opportunity:

“Always a wonderful night when it’s a night at the Opry! I consider myself so incredibly blessed to be a part of this family! Thanks for the love.”

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