INTERVIEW: Hailey Whitters on Collaborating With Her Friends and Idols

Iowa-born singer-songwriter Hailey Whitters has recently released the deluxe version of her debut record – The Dream, with five new tracks featuring mammoth collaborations with the artists that have moulded her into the artist that she is today. In this interview, we delve into what the collaborations have meant to her and how she selected both the songs and the artists for the deluxe part of this project. Stream Living The Dream everywhere now.

Hello, how are you?

Good! How are you doing?

Not too bad! Congratulations on this amazing deluxe record – it’s got to be one of the albums of the year. How are you feeling since its release? 

Yeah, I’m feeling great. I’m so excited that it’s out – I’m really proud of it. I am just such a big fan, a big fan of all of the artists I got to work with and I’m really excited about it.

I mean The Dream was just the dream, it’s an incredible project. Did you always know that you were going to add on those additional tracks and expand the project like that, or did that just evolve over time? 

Actually that was totally a quarantine idea to do the deluxe version. We had just put out The Dream and we were in the middle of touring with Jordan Davis and then the pandemic hit. We were like ‘okay, now what should we do?’ We just did what we do best and went back into the writer’s room, back into the studio. My producer Jake actually came up with the idea of doing the deluxe – his thought being ‘you keep saying that you’re living the dream, well let’s show the fans that.’ I thought it was such a great idea, a smart way to get to really show fans the full circle journey of where the dream started for me and everything that’s got to happen since. I’m so excited that it’s out.

You look through the track listing and collaborations that you did and I feel that you’ve touched every part of the country genre as it is today, but these are also people that are incredibly important to you in your journey. What was the process of selecting the artists and matching different parts of your different story to the artists and songs? 

We were looking at the story – like, how we do we tell a story? Who’s been instrumental in my story? Then what kind of songs do we have that fit the concept that might also blend really well with those artists? I feel like the Jordan songs a little more pop-influenced country, for instance.

The Little Big Town track was such a joyous celebration of country music. 

Before I even knew that song was going to be a duet, we were thinking ‘who would be good on this,’ with no harmonies, it was just a no-brainer. Yeah. So, it was a little bit of both – how are we going to tell this story and then what songs do I have in the catalogue that tell my story and would represent their brand as well.

I think that’s what’s interesting about this project – you didn’t go through every obvious collaboration. They were people that were important to you, for instance with Hillary Lindsey and Lori McKenna – there are some incredible songwriters on there. Was it really important to piece through your roots and your start as a songwriter? 

Hillary and Lori were two of the first big songwriters that got in a room with me before I had anything going on. They were taking chances on me as a writer – it was more that approach rather than my roots necessarily as a songwriter. I mean, I hope that my music always has a little bit of my roots, like where I’m coming from and where I grew up and also where I’m coming from, as a girl who was a diehard country music fan her whole life, you know what I mean? I always want to pay homage to the country music that came before me, because that’s just what inspired me to move here and to do this.

The Trisha Yearwood duet was definitely a special part of the project. Was that a pinch-me moment, because obviously ‘She’s In Love With The Boy’ was such a huge moment in country music and a formative song going up?

It totally was. I mean, when we got that phone call, Jake and I were just jumping up and down – we could not believe it. I mean, for me, that is just such a huge, huge, huge bucket list moment. I remember singing ‘She’s In Love With The Boy’ into my hairbrush microphone and forcing my family to sit and perform to them. So to have that moment and share it with her, it was so surreal. We got to do a little thing in the studio the other day – we were micced up six feet apart across from each other. Even just singing that like with her and to her – because when she put her vocal on that we were in the thick of the pandemic. To get to do it now and have that moment where we can be looking at each other from across the room – I was smiling like a big dope. I’m sure she thought it was hilarious. I was just beaming ear to ear – I get to share that moment with her that means so much to me.

I can only imagine. It must have been strange having to record most of the duets remotely, rather than feed off energies and harmonies. 

Yeah, it was pretty strange, because it did have to happen remotely. There was a few that we were able to do safely – in the studio – everyone had masks on and stuff, the LBT one we got to do in the studio, that was really cool to get to hear those voices all together. It was really surreal, but yeah some of them were remote – Trisha was remote, Hillary and Lori were remote. It was just the way it is.

At the end of the day, it’s still a pretty good result to have come out of the pandemic and 2020.

Totally.

So this is the culmination of The Dream, what do you think will follow this project? Where is it going to go? 

I’m really excited for what’s next, I’ve had so much time to just write songs and create and think about what’s next. I’ve got some projects up my sleeve that I’m really excited about, but I’m just having fun making music. I got to go out on the road and do some socially distanced shows last weekend and that was the first time that I got to see those songs with a live audience. It’s been cool – the best reminder that hopefully we can get back to live music soon. It was the best little tease, but I’m excited to get back into the studio and to focus on performing these songs.

I was going to say that one of the things with your songwriting is your amazing specificity – you talk about the Revlon lipstick on ‘How Far Can It Go’ and the details of Janice at the Hotel Bar – so has it been frustrating during the pandemic, where you only have four walls for inspiration? 

It’s been so bizarre because I like to say that a lot of the time my job is to be a professional people-watcher, and I’ve had no one to people watch – I’ve had no one like we’ve been locked in our houses. Somehow, I wonder where I pulled it from, because I was writing every day and you lean on your co-writers for really great ideas. I feel like this next batch of music that I’ve been working on, I’ve been really, really inspired in writing about where I come from – and that all lives up here [in my head]. I was raised in a small town and I remember the people that raised me, that has been kind of a blessing. I think creatively during the pandemic, because I didn’t go out, I had to turn inwards.

We’ll be listening out for more introspective music I guess then! And can’t wait to hopefully see you on the road before too long!

I know I can’t wait and I’m so excited, I hope I get to get over there soon and perform.

Thanks Hailey!

 

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