Country musician Hailey Whitters carves her own path to ‘The Dream’

The Nashville singer and songwriter, who performs at A&R Bar on Thursday, found success outside of the traditional major label/country radio machine

Andy Downing
Columbus Alive
Hailey Whitters

Hailey Whitters anchored her breakout song “Ten Year Town” in the frustration she felt spinning her wheels in Nashville, working a job as a waitress while trying to carve out a career as a country singer and songwriter over the course of a decade.

“The new ‘It Girl’ fresh off the bus/She cut right in front of the rest of us,” Whitters sings on the track, which appeared on her 2020 album The Dream. “I need longer lashes and a shorter dress/To be that overnight success.”

“Everyone has always said Nashville is a 10-year town, and I heard that [expression] and thought, man, that’s interesting. I’m on year 10 right now,” said Whitters, who pitched the song during a few writing sessions only to have it rejected as “too niche” and “too Nashville.” “So, I threw it out to Brandy Clark when I finally got to write with her. She’s someone I admire as a songwriter and an artist, but she’s also someone who has been in town a long time, and I assumed she had her own frustrations. … We started the song that day, and it was like therapy, venting and talking about the business. And I remember finishing it, turning it in to my publishers and thinking, ‘There’s something here,’ even if I didn’t know what it was yet.”

Released to social media early in 2019, “Ten Year Town” gained momentum on streaming sites, eventually landing Whitters a slot opening on tour for Maren Morris and attracting the attention of major labels that had spent the previous decade ignoring her, which earned a healthy dose of side eye from the musician.

“You have a little bit of a chip on your shoulder, like, ‘Oh, you want to talk to me now, hm?’” said Whitters, who will headline A&R Bar on Thursday, Feb. 17. “But it was also cool, because people blowing that song up allowed me to quit waiting tables and commit full-time to being an artist and musician.”

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Whitters, who moved to Nashville from Shueyville, Iowa, experienced a number of successes prior to “Ten Year Town,” landing a publishing deal with Carnival and writing songs for Martina McBride and Little Big Town, among others. But the success of the song — which found its audience outside of the major label/country radio machine — opened doors that had to that point been closed to the artist, who eventually paired with Big Loud Records and Songs & Daughters to release The Dream via her own imprint, Pigasus Records.

“There are many ways to build a career now, and we’re not solely reliant on country radio or the traditional label system anymore,” Whitters said. “The internet kind of broke that wide open. Being an artist who hasn’t had the opportunity to go to radio, I feel lucky to have fans who are discovering my music in other ways, like streaming services or YouTube or word-of-mouth. I feel like I’ve had to build my career in a nontraditional way.”

Of course, Whitters’ long-overdue breakthrough also coincided with an industry-wide shutdown, with The Dream releasing in late February 2020, just weeks before the coronavirus locked down much of the country. Rather than bemoaning the misfortune, however, Whitters said she spent a chunk of the pandemic writing and recording forthcoming album Raised (due March 18), parts of which were framed out prior to the pandemic, allowing the musician to maintain a brisk creative pace even as society slowed.

“The concept was already solidified, so at that point it was just about trying to fulfill that vision and make the record the best it could possibly be,” Whitters said.

At the same time, some of the songs and lines written prior to the pandemic have taken on unexpected new dimensions in its wake, including the loping, pedal steel-colored “Plain Jane,” where Whitters sings about how “it’s so last year” to cover one’s flaws, a line that conjures scenes of sitting in a company Zoom call unshaved and dressed in sweatpants. 

“I guess that was a little foreshadowing," Whitters said, and laughed. "Because it definitely feels true after the last few years that we’ve all had.”

When Whitters first moved to Nashville she said she was “distracted” at times by the allure of certain perks associated with a career in music. “When I was young … a tour bus was the dream. Or getting a song on the radio was the dream. All of those things I was kind of chasing,” she said. “Having been in town for so long and realizing how rare it is to be able to build a career on songs that you love and on records that you love, I think that’s become more of the dream and more of the goal: to forever be creating songs that move me and songs that move my fans.”

Whitters captures this subtle pivot on Dream track “The Days,” a song on which she takes stock of the past (“It seems like just yesterday/We were posing in knock-off frames”) before turning an eye to the present, acknowledging the importance of living in the moment. “Instead of counting up the days,” she sings, “I just want to make them count.”

Like Whitters' best songs (the superb character portrait “Janice at the Hotel Bar"), “The Days” is filled with vivid detail, bringing its easily identifiable narrator to three-dimensional life — a skillset the musician traced to childhood and an early love of writing. “Writing has always been a strength, and teachers would always encourage me,” she said. “I always kept a journal. I literally have a diary from 1995, when I was 6 years old.”

These journal entries gradually started to take the shape of songs as Whitters' love of country music intensified, her interest driven by female artists who received regular airplay on country radio in the 1990s, including the Dixie Chicks, Faith Hill, Martina McBride and Trisha Yearwood, among others. “It was the perfect storm, I guess,” Whitters said. “I wanted to be in country music, and I asked the guidance counselor in fifth grade how you did that, and he told me I needed to start writing my own songs. That was the moment the light bulb went off. I got a guitar and started writing songs, and everything has snowballed from there.”