Kelsey Waldon, a daughter of the wooded bottomlands of Monkey's Eyebrow, stood center stage at the Grand Ole Opry in Nashville, Tennessee, on Tuesday night as legendary songwriter John Prine welcomed her to his label, Oh Boy Records.
While it was her third time playing the famed country music institution, the label signing is a highlight of Waldon's career so far.
"I feel really, really great. I'm not sure it's all totally sunk in yet, honestly," she told The Sun after the performance. "I've been waiting for a while to even share this news. I honestly can't even believe it really."
Waldon played her own set that night before joining Prine onstage during his performance, when he announced her signing. She stayed out with Prine, dueting with him on two classic tracks, "Paradise" and "Unwed Fathers."
In a news release from Oh Boy on Wednesday, the label confirmed Waldon was its first new signing in 15 years.
"It's an honor for us to work with Kelsey," said Jody Whelan, director of operations at Oh Boy. "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."
Prine echoed this excitement.
"I am bursting with pride to have (her) recording for Oh Boy Records. Her music continues an important arc of traditional folk and country music," said Prine, newly inducted into the Songwriters Hall of Fame. "I love Kelsey's singing. Her voice is one of the more authentic country voices I've heard in a long time."
The opportunity to work with Prine and the Oh Boy team is exciting for the west Kentucky native, who considered the partnership to be the logical next step after touring with him over the past couple of years.
"They've been longtime supporters, and they're kind of a dying breed in the music business. I only think Oh Boy is going to take it to the next level for us," Waldon said.
"They're like absolute family, and I can't think of a better situation to be a part of. They support me in everything that I'm about and everybody has embraced my songs, my art and me for exactly who I am."
In addition to the signing of Waldon, Oh Boy also announced that her first record for the label, and her third in her career, is complete and expected to be released by the fall.
For Waldon, who grew up in Ballard County, success has been a long time coming.
"It felt just amazing to see her bring this dream to life on stage at the Grand Ole Opry," said Kelly Harris, Waldon's mother.
"Kelsey has always drawn inspiration from artists of all kinds in her music -- she did when she was young and she still does today -- but I think it's perfectly fitting for her to be working with John Prine because she is just such a good songwriter. His seal of approval means a lot."
Peggy Piper, Waldon's maternal grandmother, remembers riding along as Harris took Waldon to guitar lessons in Paducah during her youth.
"She was always interested in music," Piper said. "My mother was a musician, she played guitar and sang as well, and so did her father-in-law, Rollins, before her. It could be that it's in her DNA, so to speak. Both sides of my family have that talent in their blood, and I'm proud to see Kelsey carrying on the way she has."
The hard work Waldon pulled off to release her first two albums -- 2014's "The Goldmine" and 2016's "I've Got A Way" -- independently is being rewarded in the eyes of her family.
"She's done it her way all the way through," said Ricky Waldon, Kelsey's father.
"She's worked hard for it, I have to say. I'm very proud of her for sticking through it even through the most difficult parts. It hasn't been easy for her and it ain't going to be easy from here on out, but it's going to be a lot smoother."
Beyond her being rewarded for her lifelong effort, Waldon's family is filled with excitement for what the future could bring.
"A lot of people just don't realize how much goes into it, and she did so much of that on her own," Harris said.
Her father added: "She's excited and we're all excited for her. She's living her dream, and any time anybody can do that it's hard to beat."
Waldon now stands poised to take her next steps.
"I'm never arriving, always getting there," she sang five years ago in the last moments of her debut record.
When the curtain went up on the Opry on Tuesday, one thing was clear: Kelsey Waldon is on her way.