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By Lee Zimmerman
There are dreamers, and there are those for whom the dreams come true.
Singer, songwriter and visual artist Hunter Flynn knows both. A native Kentuckian, he’s a self-taught musician who’s managed to turn his goals into reality. A late entry into a talent contest gave him his first claim to fame, but ironically, it had nothing to do with the judges. He didn’t win. The clip of his performance drew more views than the winners’ clips combined, and the attention followed.
On Friday, Nov. 13, local audiences can see why when he headlines The Shed’s Smokin’ Monkey Lounge to kick off the venue’s indoor season.
“There have definitely been some benchmarks that I’ve hit that were pretty cool and let me know that what I was doing was working,” Flynn said of that early break. “I guess the biggest kind of success that I had early on was when I entered a competition called ‘Gems in the Rough’ on GemsOnVHS. I had a buddy that reached out and said, ‘Hey, they’re doing this competition. You should enter it.’ And I entered it with a song that I’d written about mental health, just kind of how I was feeling at the time, with about 10 hours left in the competition. That video’s gotten a couple million views on YouTube now, and it’s reached pretty far and resonated with a lot of people. And so I started getting phone calls from all over the country. People just wanted me to come out and play for them. I didn’t even make the top 10 in the competition. That’s the reason I posted the video, and I think by the time the competition was wrapping up, I had more views on my video than anybody else in the competition combined.”
That exposure opened the door to real-world recognition and his first public performance, just over four and a half years ago. Since then, he’s built a national following while touting his Appalachian authenticity. He calls his sound “Appalachian soul,” a reflection of the music native to the region where he was raised. He’s since played major venues and festivals across the U.S. and Europe, and he was named the Kentucky Music Hall of Fame’s 2025 artist in residence.
His success was no accident, as his 2023 EP, aptly titled “Roots,” and his new debut album, “Appalachian Soul Music,” make clear.
Still, it was an accident that changed Flynn’s life and might very well have ended it. “I was driving down I-75, no seat belt on, going 70 miles an hour in an old 4Runner, and I flipped three times across all three lanes of traffic,” he said. “All I had were just some scratches and bruises, a little bit of glass in my back, but no major injuries. It just gave me a brand new perspective. I remember kicking open the passenger door, and the first thing that I saw was the Bible that my parents had given me for college graduation, sitting on the ground. And I decided that if that wasn’t a sign from God, I don’t know what is. In those moments, I decided I was never going to spend another second of another day doing something that I didn’t love or chasing something I loved … I definitely had someone looking out for me that day.”
That desire and determination have clearly paid off. He’s also found success as a portrait artist whose ongoing commissions provide him with a dual career. “I think a lot of it, for one, is that the work ethic is a big thing,” Flynn said when asked to explain his rapid rise and dual careers. “It has always been in my family. I was raised to believe that if we’re gonna do something, we need to do it right. And then, on the other side of that, it was self-belief. My mom raised me to believe that I could do absolutely anything, which means you gotta have a little bit of delusion to chase a dream like this. So I credit both of those things a lot. But then I also had some life-changing experiences where I kind of just let go of any expectation of where this was headed, and I told myself that things would work out the way that they’re supposed to and when they’re supposed to. I just tried to make the best music and the best art that I possibly could, and I let that carry me wherever it may.”
I just tried to make the best music and the best art that I possibly could, and I let that carry me wherever it may.
Hunter Flynn
If his new album is any indication, that effort ought to carry him even further. That sound — Appalachian soul music — combines country, bluegrass, gospel, soul and Southern rock.
Many people refer to that as “Americana,” but Flynn resists the label. “I think we’re talking a lot about the same thing, but I think that saying Americana puts a little bit more of a constraint on what it is. The whole point of me calling it Appalachian soul music was to try to make sure that no one was going to put me into a box, and so I could say, this is what my sound is. To qualify to be Appalachian soul music, it just has to meet two check marks, right? One, that I am Appalachian and I am the artist, and two, I’m putting my whole soul into it. So whatever the hell I want it to sound like is what it’s going to sound like.”
Still, he can cite some early influences. “As a kid, before I ever really got into the Americana stuff and songwriter stuff, I listened to a lot of what my mom and dad listened to,” Flynn said. “They were big Leonard Cohen fans, as well as fans of Jim Croce and the Eagles. I listened to a lot of that stuff, and Mom would always turn on country radio whenever we were running around or going to sports at a young age. I listened to a lot of Toby Keith and the early Kenny Chesney stuff and things like that. But everything really shifted when I was introduced to a feller by the name of Nicholas Jamerson. He was fronting a band called Sundy Best at the time. He’s from Prestonsburg, Kentucky, and he was making music for a living and writing songs about stuff that I grew up around — stuff that I knew about — and it really just kind of opened my eyes to the fact that somebody from my region could make music for a living by talking about the stuff that we cared about. It’s funny because I never expected to make an album or anything.”
Much less make a living — which explains the name of one song on the album, “Robbing a Bank.”
“I’m a big Kentucky Wildcats fan and Cincinnati Bengals fan, and a couple of football seasons ago, I had made a parlay on the Cats and the Bengals in the same weekend,” Flynn said. “And Saturday I watched the Cats lose, and on Sunday, I watched the Bengals lose, and on Monday, the mortgage was due. So I remember sitting there and kind of looking at my bank account and thinking to myself, ‘I’m gonna have to rob a bank or something.’ Jail sounded better than what I had going on because at least they get three meals a day and a roof over their head.”
Another track, “Dreams Keep Dying,” seems somewhat out of sync given all he’s achieved, but Flynn said the song was written very early on, before his current circumstances. “In the first couple of years, it felt like the dreams were dying over and over and over again. I think we wrote it in the hopes that for people that are doing that same thing early on, getting knocked down time and time and time again, it just might encourage them to keep on standing back up and keep on chasing it, no matter how tough it gets.”
Happily, he seems to have a handle on what it will take to get where he wants to go.
“I think that I’ve just figured out a lot more of what I want my music to sound like,” he said of his musical evolution. “I’ve developed as an artist and as a songwriter for sure. I’ve experimented a lot more. The biggest thing is just about growth, just having more of an idea of what I’m capable of and what direction I want to go in.”
With 400 shows under his belt to date, Flynn finds himself in the midst of his first headlining tour, which will total some 32 dates by the time it’s over. The Shed show is his second at the venue; he opened for the Wilder Blue there earlier this year.
Flynn said audiences respond to the honesty. “I’ve had a lot of people comment on the authenticity of it,” he said. “I’m not trying to sing about tailgates and partying and all that stuff that you hear a lot of these days. But still, I feel I did a pretty good job of just talking about the stuff that I’ve been through and hoping that if it relates to me and if it’s true to my experience, then there’s somebody else out there that can relate to it who has been through something similar.”
Meanwhile, a day off in Nashville means catching up on neglected domestic duties. “We actually just got back into Nashville last night,” he said. “I’m doing laundry and packing the van back up, and we’re leaving again Thursday night or Friday morning. I gotta keep doing some stuff myself, or else the ego will get so big I won’t be able to fit through the doors.”
If you go
Who and what: Hunter Flynn’s “Back to My Roots” tour, with Sierra Carson
When: 8 p.m. (doors 7), Friday, Nov. 13
Where: The Smokin’ Monkey Lounge at The Shed, 1820 W. Lamar Alexander Parkway, Maryville
How much: $19.20 in advance (includes taxes and fees)
Tickets: theshedmaryville.com
