Hailey Whitters is one of Nashville’s unsung people. She released her own underappreciated record, Black Sheep, in 2015, and since then has been in the background written songs for some of the biggest artists in town. Last year she returned with an excellent new record, The Dream. I had the chance to talk to her about it back then, in the halcyon days before the pandemic, and thought it was worth re-publishing now due to the success of the record, and now its subsequent re-release as Living The Dream.

Hey Hailey, so, you’ve said The Dream is the first music you really see as 100% you.

I feel like I kind of had it prior to making this record. I had hit this point where I kind of let go of any expectations for myself. And it really freed me up creatively to really experiment and just really be confident in this new sound, in this new music that we were making.

I also think the fact that I literally had a hand in it from day one, just the writing of the record, the producing of the record, you know, sitting there in the room when it was being mixed, I was just so intertwined into the creating of this record that I just feel like for the first time it felt like the most probably authentic representation of what I was creating.

Was it a conscious decision to be involved in all aspects of it?

Yeah, I mean it kind of was out of necessity. I'd been trying a few different projects, working with a few different people in town and just had yet to find the producer that I really felt was showcasing my work the way I wanted it to be. And so I just kind of fell into that role.

So my boyfriend, Jake Gear, and I, kind of just wore that hat out of necessity. We didn't have a producer. So we say that we jumped off the deep end and just learned how to swim. And so it was really just an experimental process. I think there's a beauty in us not having done any producing before because we really had to find our way through it.

Did you have a sound or a picture in your head of how it was going to turn out when you went in?

I mean, we would kind of sit and listen to songs that became, kind of the inspiration behind some of the production of some of the songs. But we really leaned heavily on the musicians and the players that we hired. We’d worked with them on previous projects and we really trusted them, they know so well what is right or wrong for a song. We would come in with maybe a vision for the production of a song, but really relied on the players to kind of deliver that.

So you were pretty much learning as you went. I guess you haven’t really been on the other side of the desk in the past.

Yeah. I had worked on demo sessions and stuff and I made Black Sheep a few years ago. But I wasn't in the producing role as much. I definitely had opinions, you know, “lean a little more this way”. I was definitely vocal about executing the vision, but also wanted to give the musicians the space to really bring the song to life.

You just mentioned Black Sheep what do you think is the biggest difference between that and The Dream?

I feel like I grew up a lot in between those records. I still really love the Black Sheep record and I don't regret any of the songs on it. But I feel like this new record is me a little more rooted and a little more grounded. And who I am as an artist.

Did you feel like you had to conform to a certain expectation on your first record?

Yeah, I feel like there was a period of time, especially after Black Sheep, where I'm really trying to push myself commercially in terms of country radio and the Nashville record label. And I did a few things that never came out, I went into the studio and really tried to push myself that way, and I never released it because it didn't even feel like it was me. So I ended up scrapping that project. That's when I started to regain confidence and what I just naturally do creatively. And so that's what I feel like The Dream is really about.

How did you go about writing for the record? All in one block, or did you spread the writing out?

I needed to get a collection of songs to go through. I feel like the songs all were written within two years of making the record. So let's see, we made the record in 2018. I remember writing some of those songs in like February of 2018. I know ‘Ten Year Town’ I wrote in January of 2017.

So honestly, I feel like it was a little bit magical that those songs kind of all cohesively came together. I knew I had ‘Ten Year Town’ and I knew I had ‘Heartland’. ‘The Faker’ I think was one that was kind of written a few years ago. So I knew I had some songs, but it wasn't until February of 2018 when I wrote ‘Janice Ath The Hotel Bar’ and a song called ‘Living The Dream’ that I really felt solidified the concept of what the record was about.

I feel like I'm a songwriter first and foremost. So I’m constantly writing for myself or for projects that I might want to put out someday. But yeah, these songs definitely weren't a focused one-month period, I was just giving them space to come about. I guess when they did it worked perfectly that they all kind of cohesively came together at the time.

You collaborated with some great songwriters on the record. How do you approach co-writing?

Writing with Lori [McKenna]… it just feels so effortless. I think she just has a natural way of delivering a big emotion in a really simple beautiful way. It's so surprising how natural it feels, working with her.

Who else? So, Nicolle [Galyon], ‘Heartland’ was the first song I'd ever written with Nicolle. And she's just absolutely great. She's such a craftsman when it comes to songs. We've gone on to write several other things that I'm really proud of. Who else? Who else? Brandy Clark is obviously incredible. ‘Ten Year Town’ was actually a two-day write. Not because it was difficult, but because we end up talking so much. But she's just absolutely incredible in her songwriting, it's an honor to get to write with her.

‘Ten Year Town’ is a great song. It feels like a calling card for where you were and where you are.

Absolutely. And that's like why we felt that it was important that the record starts on that song, because it was very much feeling like my time had passed and maybe it was time to hang up the dream. So it's definitely the beginning of that period where I was re-evaluating what my dreams were and what they meant to me and what I wanted them to be.

So do you have a particular way that you like to write with different people? When you write it with lots of different people, do you kind of fit in with how they like to do or do you just get together and see what happens?

Yeah, you kind of follow the energy in the room. I tend to get really excited about great ideas. Great ideas are so hard to come by but if you have one, I find that writing it is just really easy. It just falls out. But I like to follow the energy in the room, try and keep it light and in a good space and try not to overthink things too much.

Do you know when you've written something that's just a really great song?

Yeah, I think it's kind of two different things. For me, I'm so lyric driven, so if I'm writing a song and it feels really great lyrically, then I get that feeling like, “oh, this is really great, this is something really special”. But there definitely were songs on the record that I maybe didn't. Like it wasn't on my shortlist of things I wanted to cut. And that's another reason why Jake, is such a great creative partner, because some of those songs, he made me cut them. He opened my mind up to getting in the studio and tracking it. And some of those songs are some of my favorite on the record. So I can be very lyrical and Jake can be very production-centric. That's why a conversation with him about it is great, for both of us to explore both sides.

There are a lot of really great, really clever lyrics on the record as well. Is there any one line in particular that you’re really proud of?

I am so proud of ‘Janet At The Hotel Bar’, I just think the message in that song is something that I was really needing to hear when when we {Hailey wrote the song with Lori McKenna] wrote that song. But I just I love the message. I love the storytelling of it. I love all of the furniture in it, all of the detail. It's always so funny to me how sometimes the most vivid detail can have just the most universal meaning for people listening. I think that song did that really well. It just feels like something that I would hope would be a timeless song and message in country music.

Have you ever been surprised with how your songs resonate with different types of people?

People latch onto things. They find what they wanted in the song sometimes. I mean, I do get surprised, it's still really shocking to me, having no radio support, no label support. [Note. Hailey has since joined with Big Loud Records and Songs & Daughters to create her own label Pigasus] It is really shocking to me to be out here on the road playing these shows and seeing people in the audience singing the lyrics. It's really surprising and it's a really cool feeling.

I made the record for me, I guess. I feel like if I'm going through something, there's gotta be someone else that's going through it. And so I'm just trying to see my truth. And, you know, it's cool to see other people going through the same thing. It's always a cool feeling seeing your songs resonate with with people from all over the world.

The support for the record has been pretty great to see as well. 

Yeah. I mean, I’m shocked. I'm shocked by all of it. After having been where I was, where I felt so bitter and so jaded about the industry, it has been an incredible thing to watch the community and, you know, the writing community, the creative community, the artists, the press, the journalists, it's been incredible to see them all rally behind an independent artist and put my music out there for the masses to hear it. That's a heartwarming thing. It just brings back that that magic that I was so desperately looking to find in the music business again. It just it fills me with hope that you don't have to have a record label to get to do these things and have these opportunities.

It literally will make me cry because it is just such it was so unexpected. And I'm just so appreciative of all the love that people are giving me

I think it's it's a testament to releasing something that's true to you. I've interviewed people in the past, some relatively big country music stars, who essentially record stuff because the label tells them to. The recognition you’re getting for this record shows that if you follow your own path, that works as well as trying to do what the labels think is going to it's gonna be really popular.

Everyone has to find the right way. I mean, I just think that it's important to do what you believe in. And that's exactly what I was doing with this record. I had no idea what was gonna come out of it. I was waiting tables. My barometer was, this is the last record I ever get to make. I want it to be something that I'm proud of.

And I just think that this record is just such a testament to me that it matters to do what you believe in. And it's important. I feel very lucky to be able to keep this thing on the road. I guess, you know, it's a really cool thing to do.

In your interview rounds, what are the songs you feel that people haven't really asked you about or come in under the radar a little bit.

I really love ‘Loose S’trings’. Brent Cobb, Eric Dylan and Philip White wrote that song. The production of that song. Brent is someone I admire so much as an artist and a writer. I'm just a huge fan of what he does. The minute I heard that song, I just put it on repeat and wanted so badly to cut it. And I'm so glad that he let me do it.

We cut a Chris Stapleton song as well. ‘Devil Always Made Me Think Twice’ and Chris is an incredible artist. I hope I did that song justice. We tracked that live in the studio with no click. It was just musicians breathing on each other's neck and just really feeling that one. I think there's such a raw energy to it.

‘The Faker’ is another song that I'm really excited about, that the recording on the record is just it was one take. I think that there's something also really raw and classic about that. I love that we didn't edit that take it all that it's just completely imperfectly perfect. That song reminds me of something that maybe Patsy Cline would have sung. It brings a really classic country element with the record.

The record starts on ‘Ten Year Town’, it kind of settles into, you know, returning home to your roots and ‘Heartland’. Flip the record. It picks up on ‘Janis At The Hotel Bar’, don't forget that there's this whole life out there, and then it ends on ‘Living The Dream’, which is the realization that, you know, whether it's a paycheck, whether it's a house, kids, kids, love, whatever it is, we're all living the dream and we're all lucky to be here to get to feel and laugh and hurt and cry and love.

To find out more about Hailey you can check out her official website. You can also see what she’s up to on Twitter, Instagram, Facebook, and YouTube.