Hard work, determination and grit pay off. Just ask Kelsey Waldon, the emerging country star from the quaint rural town of Monkey’s Eyebrow, Kentucky.
From an early age Waldon learned the meaning of hard work from stacking tobacco on her family’s farm. When she moved to Nashville after high school, she juggled her education at Belmont University with various bartending, retail and other odd jobs while simultaneously striving to gain traction with her musical endeavors.
Following 2014’s The Goldmine and 2016’s I’ve Got A Way, Waldon jumped onto the radar of Oh Boy Records, who signed her in the spring of 2019 – making her the first new artist brought into the label for over 15 years. She released her debut on the label, White Noise / White Lines, later that year.
With a sound grounded in old-school honky tonk and vivid storytelling, Waldon immediately forged a strong bond with label founder John Prine, sharing a stage with him countless times prior to his unexpected passing in 2020.
In addition to their artistic approaches, the two were also drawn to each other geographically, with Waldon’s hometown of Monkey's Eyebrow falling only two hours away from Paradise, the small Kentucky town where Prine spent his summers growing up (that he later made immortal with his song of the same name).
Following a jam-packed Americanafest that saw Waldon perform at two showcases and speak at a panel about Oh Boy Records, the artist talked with Holler about her bond with Prine, finding her way in Nashville and more for One Hot Minute.
Does being out and away from Nashville a bit give you a feeling similar to your rural upbringing in Western Kentucky?
Definitely. It reminds me a lot of Kentucky. It’s much more rural than Nashville, which is undergoing a lot of changes itself. We thought it was time for me to get out a bit to a place where I could think a bit, hear the birds chirp in the morning and be with my own thoughts.
We’re only about 30 minutes from Nashville, but honestly, I don’t go into town if I don’t have to. It’s a beautiful part of the Cumberland River out this way. I’m so happy to be back in the hills again.
You’ve been out of Kentucky for a while now but I’m curious, what was that transition to Nashville like for you at first?
Nashville was the biggest city I’d been to until I started touring. That was always the place to be when I was little. We usually went there or to St. Louis on family vacations.
It’s been about nine years since I moved down here. This is actually my second stint here now. I moved down a couple years after high school and only lasted a year. At the time I didn’t know anybody in town and was mostly working 45+ hours a week while also trying to figure out what I wanted to do with my life.
Was it during your first or second stint in Nashville that you spent time bartending at the Nashville Palace?
That was during the second time down. I worked there for close to five years. My first time in Nashville I worked a bunch of odd jobs, like at Target and other retail stores. I was doing whatever I could to pay my apartment rent.
Bartending was something that helped a lot the second time around, especially with Nashville being such a tourist town. I was able to work less days than when I was in retail and I was making way more money. At the same time bartending was a tough job, but ultimately it helped to pay for my second record I’ve Got A Way.
Hard work is nothing new to me though. Stacking tobacco was one of my first jobs growing up. I would just help our neighbors on their farms. Then when I got my license I worked at a CD store in Paducah, Ky., FYE and a bunch of other record stores.
It’s been so long since I’ve talked about any of this. Looking back on those days makes me feel even more grateful to be doing what I’m doing now.
You mentioned I’ve Got A Way being the album that helped get you touring and playing music full-time. How long after that did your connection with Oh Boy Records come about?
It took a while. I was still struggling at the time and living off of money I’d saved up. I was still working at the Palace on occasion when I wasn’t on tour. Things started picking up when I bit the bullet and gave up the side hustles. I view those times as an investment and learning curve that helped me get to where I am now.
The Oh Boy signing didn’t happen until 2019, but I actually tracked White Noise / White Lines, my eventual debut for the label, in late 2017. For all of 2018 I was sitting on the album and trying to find a home for it. I had a great team around me, but a label was the elusive missing piece to the puzzle.
For the longest time it seemed like nothing was going to happen with the record. But I had faith, showed patience and waited for the right opportunity to happen.
I knew after I’ve Got A Way that something had to change, that I needed to find a label for White Noise. Everything before it was done independently with me figuring things out along the way.
It’s been a couple of years since the signing and things feel much more stable now, but it certainly didn’t at one point.
Do you recall your first interactions with the label?
I’m pretty sure they knew me from I’ve Got A Way, which makes how things turned out even more serendipitous. Everyone at the label has always been supportive, but I didn’t think much of it at first because Oh Boy was John’s label. He hadn’t signed anybody in so long and Tree Of Forgiveness wasn’t even around yet.
I first met Fiona [Whelan Prine] while playing a tribute show for John benefiting Jessi Zazu of Those Darlins at the Basement East [in July 2017]. I’ll never forget it. She took a picture with me and said she was going to send it to John. I was shocked. I couldn’t believe they actually knew who I was.
She also passed along some encouraging words to me that night that I’ll never forget. She said that what I do is really special and to keep my blinders on, always looking forward. Then she said that she was going to work on getting me on some of John’s upcoming tours. I was speechless.
I met John for the first time on the Cayamo Cruise in 2018. I got to sing ‘Paradise’ with him there. It was just a relationship that was completely organic and kept growing. When I did shows with him, especially the first few, I was always in awe. The duets were always a big deal. I remember pumping myself up because I could not screw up when I’m singing with John Prine.
After that I feel like the rest was history. John was such a kindred spirit. Obviously I’d been sitting on my record for a while, but everything came together well because Oh Boy was just starting to look at signing some new artists. I’m honored to be their first in 15 years. It’s all been a whirlwind.
You just mentioned a couple of moments, but are there any other profound memories of John you have?
There are so many moments that stick out both on and off the stage. I remember doing a bourbon tasting with him for No Depression that was really fun because he’s more of a Handsome Johnny kind of guy then a Kentucky bourbon guy. But of course, he did it for me and the label.
All The Best Fest in the Dominican Republic [in November 2019] was wonderful too. When I think back on it now I just can’t believe how we were all there and how we’ll never get to experience those same moments again.
I was also thrilled to sing with him at the Ryman during his two-night run there on the Tree Of Forgiveness Tour. I was over the moon to do that because I had so many friends and supporters in the crowd for those shows who were really surprised to see me up on stage.
There are so many moments. I just enjoyed being in John’s presence and feel incredibly lucky for the time I got with him. His sense of community and everything about the later years of his life taught me a lot about what I want out of my career moving forward.
I think it’s safe to say that every moment spent with John Prine was a profound moment.
For sure, and I wouldn’t say I took it for granted, but I don’t think that any of us realized that we were in the last years of John’s life. A lot of people look back on the past and what they could have done differently, but I just feel incredibly grateful that any of it happened and that I got to be so close to one of my musical idols.
Kelsey Waldon’s highly anticipated sophomore album on Oh Boy Records is expected next year.
Photography courtesy of IVPR