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Riley Green & Randy Houser Team Up To Honor Toby Keith With “Should’ve Been A Cowboy” Duet At Sand In My Boots Festival
A dynamic duo.
This weekend, Riley Green played Morgan Wallen’s inaugural Sand In My Boots festival in Gulf Shores, Alabama, where he surprised the crowd with a duet of Toby Keith’s hit “Should’ve Been A Cowboy” with Randy Houser, who also performed at the festival. It’s a song Riley sings at every concert, and is always a crowd favorite, and it looks like they were loving hearing it on the beach too.
“Should’ve Been A Cowboy” was released in 1993, which was included on Keith’s self-titled debut album. The 4x Platinum song peaked 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 1990s (and rightfully so).
Yeah, it’s true… the first song he ever put out became the most-played song on country radio in the ’90s, which was a golden era of country and produced so many classics like “Friends in Low Places,” “Any Man of Mine” and “Boot Scootin’ Boogie,” just to name a few. That’s no easy feat, and calling it impressive doesn’t feel like anywhere close to the description that really deserves.
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.’”
Classic… and the rest was history.
It’s amazing to think that Keith came out of the gate swinging with a song like this, and he’d follow it up with an impressive 20 #1 hits throughout his career. Of course, anytime an artist spotlights his legacy it’s great to see, and Riley does it very often, and like I mentioned, has been covering this one for years.
Randy Houser has to be one of the most underrated artists in mainstream country, too, and he has an incredible voice that really isn’t talked about enough. I’ve seen some cool videos from this festival, but this had to have been one of the highlights:
@natnine Should’ve Been a Cowboy | Riley Green & Randy Houser #SandInMyBoots #MissKitty #ShouldveBeenACowboy #Rodeo @Riley Green ♬ original sound – JustJames
They also teamed up for a little “Courtesy of the Red, White, and Blue.”
@xbrittchristine Core mem for sure #sandinmyboots #rileygreen #randyhouser #courtesyoftheredwhiteandblue ♬ original sound – xbrittchristine
Last August, Randy released a new version of his song “Rub A Little Dirt On It” with Riley:
The post Riley Green & Randy Houser Team Up To Honor Toby Keith With “Should’ve Been A Cowboy” Duet At Sand In My Boots Festival first appeared on Whiskey Riff.
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