INTERVIEW: Nashville singer-songwriter Hailey Whitters living ‘The Dream’ of her own making

Hailey Whitters

Hailey Whitters. Courtesy photo.

Just last summer, Hailey Whitters was still waiting tables at a mom-and-pop Cajun café outside of Nashville.

Jordan Davis, Hailey Whitters
8 p.m., Thursday, March 5
Ace of Spades, Sacramento
Tickets: $25.

In the weeks and months since then, she’s toured with Maren Morris and Brent Cobb and released a batch of songs that has the country music community buzzing about her songwriting prowess.

“My grandma told me at Thanksgiving that it’s so weird that I’m famous now,” Whitters said in a call shortly after pulling into Denver, where she had a show just a few hours later. “I don’t know what makes her think I’m famous; maybe small-town famous.”

This isn’t Whitters’ first brush with success. Her 2015 full-length debut, Black Sheep, garnered some attention. She’s also had some success writing songs for artists like Little Big Town, Alan Jackson and Martina McBride.

Still, in the 12 years since she moved from rural Iowa to Nashville, she’s seen much more of disappointment and grew to dislike how she saw Music City change songwriters like herself. She arrived starry-eyed and expecting success at any moment.

“I had my head in the clouds; like, in a second, I could be discovered and just be on a tour bus and massive country superstar,” she said.

In many ways, her new album, The Dream, is a story of how her personal dream has changed. The naivete is gone, but so is her desire to become a star based on the country music industry’s expectations of stardom. She stopped caring about writing the songs she thought she needed to get there.

Instead, she began to balance her life. She stopped viewing success through hyper-focused tunnel vision lenses. She had put everything else in her life on the backburner, but she wasn’t going to do that anymore.

“It’s not so much what I’m doing professionally that matters to me, but also just building a great life and having a personal life. That’s kind of become the dream,” Whitters said.

Whitters describes her former self as a “yes-girl.” She felt like she had to say yes to every opportunity presented to her to succeed. After all, she had no personal or familial connection to Music City.

She would walk into bars and ask bandleaders for an audition, started playing bars, attended many songwriters’ open mic nights.

“Then I was waiting tables, and I was a receptionist at a hair salon for a while,” she said. “I was just wearing a bunch of different hats for a while. I ended up signing with Carnival Publishing Company in 2012, so I was a staff songwriter there, too.”

It’s been a struggle to learn to sometimes say “no.” But in doing so, she found some clarity.

“I’ve been there for 12 years and had many day jobs to try and pay my bills. To make this record, I went back to waiting tables and just kept writing songs and persevering. I mean, it’s a hard business.”

To fund The Dream, Whitters and her producer and long-time boyfriend, Jake Gear, also sold one of her guitars, cashed in her royalty payments and dipped into their savings. Gear asked her if she wanted an engagement ring or money to help her fund the record. She chose the record. Perhaps one will fund the other.

She said she had no other options. No record label showed any interest.

“It was very humbling. You have a whiff of success, and then you’re back to waiting tables,” she said. “I also kind of really enjoyed it because I feel it gave me great perspective. It feels good to be able to cash in a paycheck and put it towards making an effort you believe in and not being told what songs to record and stuff. I kind of saw it as a way for me to be able to do what I love still.”

The struggles and her changing outlook informed her first single from the new album, “Ten Year Town,” which she cowrote with Brandy Clark and shared on Instagram a year ago this month. The song, which immediately got the attention of some in the industry, also addresses impossible standards of perfection and beauty in country music for women.

It’s as timely now as it was when Whitters first released it. In the past few weeks, the underrepresentation of women on country radio has had a light shined on it. Whitters acknowledges the problem but remains optimistic.

“I just try to focus on writing great songs … because I still think there’s a place for those. I think that they will rise to the top,” she said. “I think it’s great that a lot of these platforms are starting to be really vocal about it and educate the masses about it because I think there’s a lot of people out there who are maybe listeners of country radio who don’t realize there is such a stark disadvantage for women.”

Elsewhere on The Dream, she sings about self-medicating to get over heartbreak on “Red, Wine & Blue;” questions her place in Nashville on homesick ballad “Heartland,” a romanticized view of her hometown in Iowa; and enters soft-rock territory on “Dream, Girl.”

The album includes “Happy People,” a song she wrote with Lori McKenna that was recorded by Little Big Town in 2017. It was her first song to make it onto country radio, Whitters pointed out. McKenna has also previously cut her own version.

“It’s the song we can’t shake,” she said. “We’re pretty hellbent on people hearing it.”

It’s another co-write with McKenna that Whitters said speaks to her the loudest, and has taken on a life of its own on social media—“Janice at the Hotel Bar.” The song took shape after she went to McKenna with an idea to write about an older woman passing life advice to a younger woman. McKenna showed her an Instagram post by a Nashville lifestyle blogger who had spent three hours at a hotel with an octogenarian named Janice who shared some wisdom with her.

The two decided to write about this Janice, but blend in nuggets of wisdom they’ve received from the influential women in their lives, like Whitters’ grandmother who swore that a “a glass of red a day is good for the heart.”

After releasing the song in January, the blogger who first wrote about Janice shared it, and the song took off. Women began posting about their own Janice, such as the woman who got bitten by a rattlesnake and still walked the Grand Canyon, or the one who refused to see her doctor to get X-rays until she put on her rouge.

Other people began a search to find the original Janice, who turned out to live in New York and loves the song.

“It’s really powerful to see all these women post photos and tell stories about their Janices,” Whitters said. “It’s been really moving.”

To round out the album, she decided to record covers of Brent Cobb’s “Loose Strings” and Chris Stapleton’s “The Devil Always Made Me Think Twice.” The former was a song she listened to on repeat after first hearing Cobb’s demo. For her version, she decided to record a gender-swapped take. The Stapleton song, meanwhile, acts as a sort of link between Whitters’ two albums.

“It’s a really broody, sexy song about this girl that just likes to sit and drink whisky alone, and you never know what she’s gonna do next,” she said.


After releasing a second single, “The Days,” in 2019, management offers began to come in. Still without a label, she and Gear decided to stagger release dates. She released the first half of the album as an EP, The Days, last fall. This proved to be an effective strategy, in part because it kept the buzz building over the winter.

“To me the record is two parts. It’s The Days and The Dream, and the days make the dream,” she said. “The dream is comprised of so many of these days that we don’t even realize we’re in when we’re in them. … I’m kind of old-school in the way that I just want to drop a record, but it is a very unique time to be releasing music right now.”

The rest of 2020 is shaping up to be even busier for Hailey Whitters, who’s supporting Jordan Davis before jumping on Tanya Tucker’s tour. More tours have been finalized though not announced, and she’s already got another album in the works.

“I know this record is new to everyone else, but it’s a few years old for me, so I would like to be able to release another song or two later this year from a new project.”

One thing she won’t have to worry about for the foreseeable future? A day job.

“I hung up the apron strings,” she said.

Follow editor Roman Gokhman at

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