Kelsey Waldon Signs to Oh Boy Records, Sturgill Goes Bluegrass

It wasn’t just your average Grand Ole Opry presentation Tuesday night (5-28). The beginning of the evening saw Bill Anderson, Town Mountain, Dustin Lynch, and Striking Matches perform before the intermission, which was entertaining enough. But when you noticed that country traditionalist Kelsey Waldon was scheduled to perform in the same segment as John Prine, and that Sturgill Simpson was given his own extended 30 minute set to close out the show, you had a sense something special was in the air for the evening.

Kelsey Waldon came out first to sing “There Must Be Someone” from her 2016 record I’ve Got a Way, and then a new song she said would be appearing on an upcoming record. What we would find out later is that Waldon’s new album would be released on John Prine’s Oh Boy Records as the independent label’s latest signee.

After Prine took the stage amid a warming welcome by announcer Bill Cody, he sang his well-known song “Spanish Pipedream,” and then his latest signature song “Summer’s End,” before inviting Kelsey out on stage with him. “35 years ago, my late business partner Al Bunetta and me, we started an independent record company called Oh Boy Records,” Prine told the Opry audience. “And this young lady that’s coming back out here, she’s already been out, but I’d like to have her come out and sing a couple of songs because today she’s the newest member of Oh Boy Records.”

The two proceeded to sing Prine’s “Unwed Fathers,” and later “Paradise”—the legendary song about Kentucky’s Muhlenberg County—which as a native of Kentucky’s tiny Monkey’s Eyebrow community, Kelsey Waldon can certainly relate to.

“It’s hard for me to put into words what it truly means to me to be signed to Oh Boy Records,” says Waldon about the signing. “To have someone like John, who I have looked up to my whole life, who I have set my songwriting standards after and my general music making standards after, to have someone like him endorse my music and care enough about it to make sure it reaches a wider audience…that means everything.”

Kelsey’s family farmed tobacco and raised cattle in the western part of Kentucky near the Ohio River, and the stories of struggle from of America’s rural heartland drip from her songs. Her last album I’ve Got A Way was a slyly thematic work that found Waldon asserting her own identity and freedom in a world that constantly is attempting to reshape and sway her towards its own image and desires.

“All I have ever wanted in a label home was for it to feel real, like a little family, and for a label to really ‘get it,'” Waldon says. “I couldn’t ask for a better dream team, in all seriousness. I’m so thankful I kept on my true north. After everything I’ve been through up until this point, Oh Boy feels like home.”

“It’s an honor for us to work with Kelsey,” says Director of Operations at Oh Boy, Jody Whelan. “There is an honesty and commitment in her music, both as a performer and songwriter, that we’ve long admired. Evident in all her work is a strong point of view, and a reverence for the culture and history of country music and songwriting, she is exactly the type of independent-minded artist that Oh Boy Records was founded to support.”

After the big announcement and duets from John Prine and Kelsey Waldon on the Opry stage, fellow Kentuckian and close John Prine friend Sturgill Simpson stepped into the famous circle to close the night out. It was a little hard to know what to expect from Sturgill since he hasn’t been touring much lately, and hasn’t appeared on the Opry in four years. Lately his live show has involved a lot more amplification and improvisation than what is customary on the Grand Ole Opry stage. But instead of an extended acid jam, Sturgill went full tilt bluegrass on the Opry crowd, with well-known mandolin player Sierra Hull sitting among other special guests, and drummer Miles Miller playing simple brushes on snare.

Sturgill proved how his roots have always been in bluegrass, first playing an acoustic version of his song “Long White Line” before launching into “Pretty Polly,” “Two Dollar Bill,” “Sharecropper’s Son” by The Stanley Brothers, along with a bluegrass version of “The Promise” thrown in there. The band then revisited “Two Dollar Bill” to take the show out in a unique set from Sturgill worthy of archiving and bootlegging for the future, and will leave Simpson fans hoping he makes good on his threats over the years to release a pure bluegrass record someday.

Tuesday night’s Grand Ole Opry show will be archived on their website soon for those who don’t want to fight through poor cell phone footage of the performances. The special moment between John Prine and Kelsey Waldon can be seen below.