Editor’s Note: In celebration of Women’s History Month, You Sing I Write is highlighting female country artists and songwriters throughout March.
Hailey Whitters moved to Nashville 13 years ago to follow her dream of becoming a country singer. Her latest album, Living The Dream Deluxe, was released in February and follows the singer’s long journey of navigating Music City, while also sharing elements of her small-town Iowa roots.
“My mom brought me to Nashville when I was 15-years-old and we went to the Grand Ole Opry,” Whitters tells me over coffee at Nashville’s Falcon Coffee Bar weeks after making her Opry debut in 2019. “That curtain went up and I saw those lights and that was the moment I was like, ‘This is what I want to do for the rest of my life.’”
Whitters has had several country artists record her songs including Little Big Town (“Happy People”), Alan Jackson (“The Older I Get”) and Martina McBride (“Low All Afternoon,” “The Real Thing”), and now the singer-songwriter is sharing her talent with the world. In 2020, she signed a record deal in partnership with her own label, Pigasus Records, and Big Loud Records/Songs & Daughters.
Below is an excerpt of my interview with Whitters from 2019 shortly after she released her EP, The Days, which she self-funded.
When was the moment you knew you wanted to be an artist?
I come from a non-musical family. I always had this draw to country music, and I have a memory of sitting on the back of my dad’s lawnmower while he mowed the lawn, singing to myself. I think I always had a really strong pull to writing. I remember being in elementary school, and I had a guidance counselor who knew that I had this passion for it, and he asked who I like. I liked the Dixie Chicks and the Spice Girls. He was like, “Well, you know the Dixie Chicks write their own music.” So then I got a guitar and I started dabbling with that.
What was the first song you ever wrote?
My friends and I, we would try to start a chick band on the playground in elementary school and Spiceworld had just come out. So we were making up dances and pretending we are the Spice Girls. We wrote this one song. I’m trying to remember how it went … I remember the feeling of writing a song back then. It felt like you could do anything and that’s still a feeling I get today when I write a song that I just love. You walk out and you feel like you’re on top of the world.
What’s the most autobiographical song on your EP?
“Ten Year Town” is probably the most autobiographical song because it feels so up-close and personal. [It’s] very much like my broken heart ballad to Nashville. I wrote that song with Brandy [Clark] two years ago and I was only 10 years into [living in Nashville]. Jake [Gear] was like, “You should change it. You’re only here 10 years.” It’s been this weird universe thing that we’re finally releasing it and I am 12 years in. It was just a weird timing thing.
What’s the story behind “Heartland?”
I was feeling really homesick and just questioning like, “Well, what’s my place in Nashville?” I was writing with Nicolle [Galyon] and Forest [Glen Whitehead]. Nicolle is also from the Midwest, so we started talking about going home and Nashville. [Songwriter] Barry Dean told me once, “Nashville will try and change you and make you someone you’re not. It’ll make you forget who you are and it’s important to find that place or those people that you can go to that bring you back.” That’s always been the Midwest [for me]. The Heartland and everything it stands for: hard work and honesty and good people. That is what always draws me to the Midwest. I like to go back a lot. It keeps me grounded.
For more of my interview with Hailey Whitters, visit Billboard. Her latest project Living the Dream Deluxe, which includes “Fillin’ My Cup” featuring Little Big Town, is out now.