Hailey Whitters on the Watershed Moments That Made The Dream a Reality

Sure, Hailey Whitters is 12 years into a ten-year town. But her brand new full-length album The Dream? It’s the kind of album that just feels like it took a while to craft. Like she didn’t hastily throw together a mix of quick writes in order to get something out there. Country music of this caliber cannot be rushed.

But still, when Whitters and I sat down to talk about the album (due out on Feb. 28), I wanted to know what the turning point was for her and her music.

CMT.com: In “Ten Year Town,” you talk about being too far in to turn around because you’re twelve years into a ten year town. What was it that changed for you, after waiting all those years?

Whitters: I don’t even know. When I put that song out, it felt so honest and so real to me and to the other dreamers in this town. We’ve all got our moment. For me, I feel like Maren (Morris) really blew things up for me when she invited me to go on tour with her about a month after I released “Ten Year Town.” When she gave me that platform to get the song out there, I think that that changed a lot of things for me.

And then Brothers Osborne used their platform — during a red carpet interview at the 2019 ACM Awards — to put the spotlight on you and your songwriting. That must’ve felt really validating.

It did. I woke up the next morning to all these texts like, “Brothers Osborne just name dropped you on the red carpet.” And I’ve never even met them. I love Lucie Silvas (John Osborne’s wife), and we follow each other on social media. So when I released “Ten Year Town,” I think she must’ve played it for him. And then I remember I was sitting at the Wilburn Street Tavern one night, and John sent me an Insta message. He was like, “Hailey, that song is so special. I’ve totally been there. I sold all my guitars. Don’t give up.” That was so cool to me, for him to be so encouraging and to tell me he’d been exactly where I was. I’ve been here for so long and met so many artists, but it’s still cool to know you have people like that in your corner.

Like the girl in the song, did you really go back to waiting tables while you were waiting on your break to come?

Yes, I went back to wait tables at Ri’chard’s in Whites Creek. And ironically enough, that was one of the first places I played when I moved to Nashville 12 years ago. So it was weird to go back to this little Cajun cafe 12 years later. As a waitress.

Did that feel like you were acquiescing and kind of giving up on the neon dream?

Not really, because I’d kind of come to terms with the fact that it might not ever happen for me. You’ve gotta be okay anyway. Otherwise, I’d have to hightail it back to Iowa. I came to the point where I was like, “I’m gonna make this record as if it’s the last record I get to make, before I hang it up.” And that way, I could feel like I did my thing. Like I tried, and I did what I was there to do. I think that that allowed me to take the pressure off, not expect anything, and really just appreciate and enjoy it for what it is. I guess I couldn’t quit it after all. But Maren really relit a flame in me that I just needed to have back. I was in a place where I was needing to find the magic in what we do here. And I feel like the response to “Ten Year Town” and touring with Maren and the CMT tour, that all reignited that fire.

That really comes through on this album. It’s like I can really hear all the female artists who influenced you while you were a kid in Iowa. Was that your intention, to keep your country as country as the songs you grew up on?

I’ve always looked for authenticity and honesty in music. And if that means it has a track loop to it — if it’s real and authentic — I can get down with that. I do think that art has to evolve, though, otherwise we are all going to be hearing the same things all the time. I try to think about what it has to sound like and what the subject matter has to be, but also, is it honest and relevant to the word we’re living in? The music I grew up on that made such a huge impression on me — the Dixie Chicks, Shania Twain and so many artists at the time — were probably being criticized by traditionalists. They were probably saying, “That’s not country music.”

You don’t look old enough to have been at this for 12 years. You must’ve moved to Nashville when you were very young.

I left Iowa right after high school, when I was 17. I was naive. I knew nobody here. My parents were scared for me, but they saw that I had this drive and ambition and that I was hell-bent on living down here.

Whitters’ next stop is on Feb. 27 — on the eve of the release of The Dream — at the Knitting Factory Concert House in Boise, Idaho. And on March 10, she’ll be playing the Basement East in Nashville and she is real damn happy about it.

The Dream track list:

“Ten Year Town” (Hailey Whitters, Brandy Clark)
“The Days” (Whitters, Hillary Lindsey, and Ben West)
“Red Wine & Blue” (Whitters, Clark, Jessie Jo Dillon)
“Dream, Girl” (Whitters, Dustin Christensen)
“Loose Strings” (Brent Cobb, Erik Dylan, Phillip White)
“Heartland” (Whitters, Nicolle Galyon, Forrest Whitehead)
“Janice at the Hotel Bar” (Whitters, Lori McKenna)
“Happy People” (Whitters, McKenna)
“The Devil Always Made Me Think Twice” (Al Anderson, Chris Stapleton)
“All the Cool Girls” (Whitters, Dillon, Brett Tyler)
“The Faker” (Whitters, Lindsey, Waylon Payne)
“Living the Dream” (Whitters, McKenna)

Alison makes her living loving country music. She’s based in Chicago, but she’s always leaving her heart in Nashville.


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