Iowans Name Their Favorite 'Underrated' Country Artists [LISTEN]

Is there a country artist or band that you wish more people knew about? Our conversation this week in the studio lead to some interesting responses! Here are a few of the country acts that Brain and I think are underrated:

Kassi Ashton

When Brain and I were discussing this topic, the first named that popped into my head was Kassi Ashton. I'm not exactly sure how I came across Kassi's music for the first time, but I think it was because she was mentioned by some other country artist that I love on social media.

I think that I'm drawn to Kassi's music because of her unique sound. She gives me some real Amy Winehouse vibes, and Amy happens to be one of my favorite singers of all time. She also seems ridiculously cool. She rides motorcycles, designs her own clothes, and is just overall hilarious. I got to see her live for the first time when she opened for another country act in Cedar Rapids, and I remember raving to the people sitting near us about how she's crazy talented. Some of my favorite songs of hers include:

"Drive You Out of My Mind"
"Dates in Pickup Trucks"
"I Don't Wanna Dance"
"Called Crazy"
"Taxidermy"
"Black Motorcycle"

She also does some killer covers of Dolly Paton's "Hard Candy Christmas" and Christina Aguilera's "Genie in a Bottle." In my personal opinion, I think she deserves a LOT more attention in the world of country music.

Midland

Brain's pick for an underrated country act is one that we both love: the band Midland. If you enjoy a traditional country sound, these are the guys for you. They have had a few songs make it to radio, "Drinkin' Problem" and "Mr. Lonely" come to mind, but their catalog of music definitely deserves a deep dive.

One of Brain's favorite songs by Midland is called "And Then Some." It's one of their slower songs off of their 2022 album The Last Resort. A few of my favorites are "Cheatin' Songs," "Burn Out," and "Two to Two Step." They also have an AMAZING collaboration with Mackenzie Carpenter called "I Wish You Would" that came out recently, and I'm still hoping that it will take off.

Hailey Whitters

And, while we're at it, let's show a little more love for Hailey Whitters! I know she has a big following here in her home state of Iowa, but I think she deserves way more attention than she gets. She's been recognized by several prestigious publications over the past few years, including Rolling Stone, which just goes to show her talent as a songwriter.

If you're new to Hailey Whitters, her big radio hit was "Everything She Ain't," but here are a few of our other favorites from her discography:

"High on a Heartbreak"
"Fillin' My Cup" with Little Big Town
"In a Field Somewhere"
"Dream, Girl"
"Plain Jane"
"Roulette on the Heart" with Conner Smith

Listener Suggestions

We asked Iowans on Facebook to share with us some of the artists that they feel are "underrated," as well as a song that they would recommend to a first-time listener. Here are some of the responses:

The Dead South - "Broken Cowboy" (released in 2019)
Casey Donahew - "He Ain't a Cowboy" (released in 2019)
Drew Baldridge - "Get Me Gone (feat. Emily Ann Roberts)" (released in 2025)
Drake White - “Hurts the Healing” (released in 2022)
Warren Zeiders - "You For a Reason" (released in 2025)
Whiskey Myers - "Midnight Woman" (released in 2025)
Cody Jinks - "Mamma Song" (released in 2015)
Creed Fisher - "The Way That I Am" (released in 2018)
Sons of Legion - "Remember My Name" (most popular song on Apple Music - released in 2021)