Emerging Country: After Writing For Little Big Town & Alan Jackson, Hailey Whitters Shares Her Music

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Welcome to Emerging Country, a Billboard series where we highlight an up-and-coming act who is making a splash in the genre. This week’s pick is country singer-songwriter Hailey Whitters, whose previous credits include Little Big Town, Alan Jackson and Martina McBride.

Hailey Whitters moved to Nashville 12 years ago to follow her dream of becoming a country singer. Her forthcoming sophomore album, aptly titled The Dream, is due out in 2020 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 Billboard over coffee at Nashville’s Falcon Coffee Bar weeks after making her Opry debut. “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.’”

Today (Sept. 13), Whitters released the first half of her upcoming project. Titled The Days, the six-song EP includes the stirring and autobiographical “Ten Year Town” and reflective new single “Heartland.” “I've been so busy chasing the dream that I've forgotten to be present for the days,” she reflects. “In reality, I think the days are what make the dream.”

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”), but now the singer-songwriter is sharing her talent with the world. Whitters self-funded the project and produced it alongside boyfriend Jake Gear, who works at BMG publishing.

“I've been really surprised and really humbled by all the things that have happened with this new music -- it’s a weird thing to make a project purely for its own sake and to see the response that has come out of it,” she says. “It's a cool feeling, and the magic that I needed to see again with Nashville.”

Ahead of spending the majority of the fall on the road with Maren Morris, Brent Cobb and Little Big Town, Whitters sat down with Billboard to share her backstory as an artist and songwriter.

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.

When was your first public appearance?

I remember it was in a middle school gym for some sort of benefit. I sang Randy Travis’ “Three Wooden Crosses.” That was the first song I learned on guitar. I auditioned for the Country Showdown, and I made it to the fair. So I got to perform at the Great Jones County Fair, which was a big fair in my town. Those two stand out the most.

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.

The first song I really remember, I was probably early teens, and it was a song about my boyfriend. It was called "This Kind of Stuff." I remember it was about young love and our parents don't like it, but they don't know anything about it. So sassy.

Who’s career do you admire most and would like to pattern yours after? 

There's a few. I love Lori [McKenna]. I love Brandy [Clark]. I love Miranda [Lambert]. I love Kacey Musgraves right now; people who have a voice and have something to say and are able to do that on a scale like they've done. They're touching so many people and I want to be able to always write songs that I love and songs that I feel matter. Having an audience that will listen to them is just icing on the cake. I hope I get to do this for a very long time.

Who is your dream collaborator? 

The Dixie Chicks. Obviously Dolly [Parton]. Everyone wants to work with Dolly. Vince Gill. Alan [Jackson] recorded one of my songs, but I would love to sing with him.

What’s the story behind “Heartland?”

“Heartland” is coming home and coming back to my roots a little bit, and coming back to who I am. Nashville can change you a lot. I'm from the Midwest, the Heartland, Iowa. I grew up in a small town called Shelbyville. We have two bars and a church. We don't even have a zip code. I grew up in a small town and I'm from a huge family and the Midwest has always been so embedded into who I am. I probably romanticize it a lot more because I don't live there anymore.

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.

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 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 best piece of advice you’ve been given about the music industry? 

Frank Liddell, my boss at Carnival [Music] says, “Write the truth. It's more interesting.” Carnival has been like a creative lighthouse for me. I wouldn't be able to be writing the songs I am today if I didn't feel so much support at my publishing company. They've always, always, always encouraged us to write what we know and to never feel stunted by the radio or the town or the trends and just write something great.

Listen to Whitters' The Days below.