In Honor Of The Country Music Highway, 23 Kentucky Artists You Need To Know!!

When I sat down to write this article, it was originally going to be just ten artists. I had so much trouble trying to whittle down my list, that I ultimately decided to write until I felt the list was full. Turns out that the magic number wound up being twenty-three, so I figure why not dedicate this article to the Country Music Highway or as the Government calls it, U.S. 23!

This list includes every genre out there, so there truly is something for everyone here. If you know me at all, talent is talent, so enjoy this musical smorgasbord. I hope you find an artist that compels you to get involved. See a show. Buy a CD. Buy a shirt. Support the artists or lose the art.

By the way, these are in no particular order. Why? because I feel rankings and things like a battle of the bands causes more division in a musical community than they’re worth. The intent of this article is for us all to lift each other up. We’ll call it “Fan-Sharing” for lack of a better term. So here goes!

First up is a young band that I have been supportive of for well over a year. Johnny Conqueroo does things their way and no one, hopefully at least, will ever change them. They’re a band that’s about as difficult to describe as it can get. Blending pop melodies with almost punk vocals and a blues backbone make them one of the most intriguing bands on our list.

Johnny Conqueroo

Otis actually has a record deal with Cleopatra Records and they just finished a European tour, so technically, I shouldn’t include them on this list. BUT, they are a band that I believe in and have done so since 2014. So for now, I get to make the rules around here, until my wife tells me I can’t. Haha OTIS come at you with straightforward rock and roll, deeply rooted in the blues. With two of the best guitar players around playing dual solos and great harmonies like many classic rockers before them, Otis is a beast!


Magnolia Boulevard is a band that I finally got to see in a live setting and I was definitely not disappointed. I mentioned the slide play in Otis above, well Gregg Erwin happens to be a fine slide player himself. Mix that in with a solid rhythm section and the raspy female voice of Maggie Noëlle, a voice that was just made for rock and roll, and you’ve got a recipe for a good time. They’re funky, they’re fun and they’re an act you don’t want to miss, unless of course you hate having a good time.

Magnolia Boulevard

Joslyn & The Sweet Compression first came on our radar by accident. We stopped by Willie’s Locally Known for some barbeque and this lovely lady and her band were doing their best to burn that place to the ground! Joslyn has that soul voice that you know only comes from growing up in Church. Lay those big ole vocals over the funkiness that is The Sweet Compression and you just can’t go wrong. Joslyn has the biggest and most powerful voice that we have found so far in Kentucky.

Joslyn & The Sweet Compression

Kelsey Waldon is a young lady that blows my mind with her sound. She has toured Nationally and I may be cheating a bit by including her on this list, but I feel she deserves it. The way traditional country is fighting its way back with artists like our own Sturgill Simpson and Tyler Childers, Kelsey is a young lady that deserves your attention. She is originally from the Paducah area, but moved to Nashville to pursue her music career. She’s a keeper y’all!

Kelsey Waldon

C2 & The Brothers Reed are one of those bands that decided to just go for it. These young men are road dogs and are out there most every day honing their craft. Their sound is a bit of a throwback to the classic rock era of the 1970’s. You’ll hear their influences immediately. Thin Lizzy, Skynyrd and even some Aerosmith, but it’s their Beatles-esque “Be Alright” that steals the show for me.

C2 & The Brothers Reed

Jeremy Short was born and raised in Breathitt County. If you’re a Sturgill Simpson fan, you’ll know that Mr. Simpson also calls Jackson home. Jeremy put together a trio called Short & Company. They’re a trio for a reason. Our ears can’t take two guitars. Jeremy is one of several slide players on this list that I’d match their skills up against anyone in the world. With a style, all their own, Short & Company have set out to create a new kind of blues with an old-fashioned flavor.

Short & Company

Eric Bolander could technically be on this list twice, but we’re going to focus on the singer-songwriter side of things. More and more artists are finally breaking through and having a successful career by playing honest, well-crafted tales that turn your emotions into puppet strings. If you’re a fan of say, John Moreland, you’re going to love Eric Bolander. Awww hell, check out his rock band, Alcatraz Shakedown, while you’re at it.

Eric Bolander

Traditional Bluegrass music is often overlooked in the mainstream world of music. These Local Honeys have dedicated their lives to not only performing traditional bluegrass, but to preserving it as well. Linda Jean Stokely and Montana Hobbs both graduated from Morehead with Degrees in traditional music. The Local Honeys are as authentic and true to traditional bluegrass as you will find and in our opinion, they’re true Kentucky treasures.

The Local Honeys

NewTown is a bluegrass band that shouldn’t need an introduction, but here we go. The band has been around for a few years, but after some member shuffling, they really began to shape their music into something fresh and exciting in bluegrass. They sought out songs and writers to help them achieve their sound. Enter into the picture, Kentucky’s newest favorite son, Tyler Childers. NewTown recorded his track “Harlan Road” and the rest, as they say, is history.


Senora May is a singer-songwriter from Estill County. Her voice has a haunting quality to it, not unlike Perry County’s legend, Jean Ritchie. Lots of people know Senora as, “Lady May”, but make no mistake, her voice and songwriting earned her spot on this list.

Senora May

Justin Wells has been a staple in Central Kentucky for years. He fronted Fifth on the Floor, who served as Shooter Jennings backing band for a bit. After the band called it quits, Justin released a very personal album and hit the road. Luckily for us, he has yet to look back.

Justin Wells

The last bluegrass band on our list, happens to be my personal favorite bluegrass band. The Wooks hail from my adopted home of Bourbon County, so a little local love may be in play here, but give them a shot. I bet ya like ’em! The addition of Aaron Bibelhauser bolsters an already stellar lineup of songwriters.

The Wooks

The Bowling Green area has produced some great bands and artists. The venues in the area have produced Cage The Elephant, Black Stone Cherry, the Kentucky Headhunters and Sleeper Agent, to name a few. Next in line is Jericho Woods. They have a modern country sound that is centered around great songwriting, beautiful harmonies and fantastic vocals. Their songs are garnering a lot of attention in Nashville and they seem poised for great things in the very near future.

Jericho Woods

Bowling Green’s quirkiest entry on this list, has to be The Josephines. Part Outlaw Country, part Bluegrass, part Dropkick Murphy’s…The Josephines joined this list to kick ass and chew bubble gum and you guessed it, they’re all out of bubble gum. Hold on tight when you hit that play button!

The Josephines

Sometimes, you hear a voice that you can’t quite say what the how or why is, but you just know it’s special. London, Kentucky’s Madison Lewis has such a voice. Madison is only 14, yes I said 14, years old, but she has a tone, a control and a power in her voice of someone much, much older. It is really rare to find someone so young that knows who they are as an artist. When you think of the most famous voices in the world, they are immediately recognizable. In time, we strongly feel that Madison will be one of those voices.

Madison Lewis

Dillon Carmichael was a part of our first music showcase at the Austin City Saloon and a big reason that it sold-out. Dillon is a throwback to the days when Country Music had something to say. When contemporary Country ruled the airwaves. For us, Dillon is an artist whose career we can not wait to watch unfold.

Dillon Carmichael

Woodford County’s Trippin Roots is a mixture of styles that just somehow works. There’s some bluegrass, there’s some pop, there’s some country, there’s some Americana, some soul, some rock and there’s a whole lot of talent which is why you need to enjoy this uniquely Kentucky band.

Trippin Roots

MOJOTHUNDER is a band that won’t be for everyone and they’re fine with that. They play plain ole dirty rock’n’roll. The kind that makes you feel like you need a shower after listening to them. When I first heard this track, I was like, is this an Ozzy cover? Isn’t this “Over The Mountain?” Then the music told me to “shut my damn mouth”, just before it hit me like a Mack truck. It’s as if Motorhead and AC/DC had a bastard child and they’re here to steal your lunch money.


If you’ve followed this site before, Tyler Booth is a name that you’ve likely read about. If not, let me introduce ya. The young man from Wolfe County has a smooth baritone voice that conjures up voices like Waylon Jennings, Merle Haggard, Jamey Johnson and Josh Turner. He is only 21-years-old, so his journey is just beginning.

Tyler Booth

Brother Smith hails from Covington, Kentucky and they’re the next artists you need to know for a ton of reasons. I’m not going to list any of them though, I’m just going to let the music do all the talking. Enjoy their video shot by Lexington’s Coleman “Bear” Saunders. Be warned, you’re gonna dance.

Brother Smith

Korey Rose is a young man who has seen a lot in his young life. Born in Eastern Kentucky, he found his love for guitar at an early age. Moved to Lexington and grew up there. He joined the Army and was deployed to Afghanistan,twice. This veteran (Thank you for your service, Korey!) came back home to Kentucky. His words have an honesty, a genuine feel to them. If you’re a fan of a smooth country crooner like George Strait or Kentucky’s Keith Whitley, you’re going to love Korey rose.

Korey Rose

You may recognize the last name of Montgomery. There’s a rather famous pair of Kentuckian brothers that have made their mark in Country Music. Walker Montgomery is the son of John Michael Montgomery and the nephew of Eddie Montgomery. Walker has a sound that is more modern country than contemporary, so he is looking to carve his own niche out and his track “Simple Town” is a fantastic start.

Walker Montgomery

I know that I left off many talented individuals and bands, but rest assured, this won’t be my last list. Stay tuned, we’re just getting started!!