Hailey Whitters Talks Managing Her Burgeoning Country Career on Her Terms

“Mowing the lawn seems to be my designated chore here,” Hailey Whitters tells the Scene, as a rooster crows in the background. She’s speaking with the Scene by phone from her family’s farm in Iowa, where she’s spent the past few weeks. “My parents have several acres, so it takes a few hours to do. I’ve been pulling vegetables from the garden every night to make dinner with. It feels good to kind of get back on the land and slow down a little bit.”

The singer-songwriter was all set for a dynamite year of touring behind her second album The Dream. The LP is a rock-and-soul-kissed slice of contemporary country, and a fine showcase for Whitters’ strong-yet-gentle, somewhat Kacey Musgraves-esque voice, as well as her outstanding songs. On March 10, just after a deadly tornado tore through Nashville and just before the live music industry began to shut down in response to the coronavirus, Whitters took the stage for a sold-out release show at Exit/In. The concert was a milestone for an artist who’s struggled to make her music heard in Music City.

“It’s been such a long journey for me in Nashville,” Whitters says. “I’ve kind of had a love-hate relationship with it, and the release of this record really got things turning for me.”

After more than a decade in town spent waiting tables and writing songs and feeling like she could do so much more if given the chance, Whitters channeled all her frustration into the song “Ten Year Town.” The track, co-written with Brandy Clark, is bracingly honest and affecting. The story is specific to Whitters’ experience, but can apply to just about anyone, as she sings, “I didn’t come this far / To only get this far.” Released in 2019, the track helped Whitters break through to a bigger audience. Though she’s yet to appear on a Billboard chart, positive reactions to the song from fans, critics and other artists (like Maren Morris and Brent Cobb, with whom Whitters has toured) have made her one of the most buzzed-about talents in the country world.

Acting as a magnifying glass on the complicated business of living is a thread that runs through the songs on the record. Many more of the stories in the tunes also come directly from Whitters’ life. She dated and got burned by “The Faker,” learning along the way that “Fancy clothes just don’t dress up ‘cheap.’ ” Afterward she drowned the pain of a broken heart, as she sings in “Red Wine & Blue.” She tackles the messy, raw edges of life as a woman that she’s navigated on her own with grit and poetic poise. But she’s also attuned to the value of what you can learn from others. The phenomenal “Janice at the Hotel Bar” is all about the transmission of lived wisdom. It shares some territory with “The Days,” a song about the beauty of commonplace experiences that we all have, but may not take enough time to appreciate.  

Hailey Whitters Talks Managing Her Burgeoning Country Career on Her Terms

“Last year there was so much momentum — I was just so busy, and this year was teed up to be even busier,” says Whitters. “In a way it’s interesting, because I am being forced to practice what I preach right now, really take a step back and make the most of my situation.”

Whitters’ talent has led to her songs being cut by stars like Alan Jackson, Little Big Town and Martina McBride. The songs on The Dream were co-written with some of the best in the industry — heavy hitters like Lori McKenna, Nicolle Galyon and Hillary Lindsey. Still, as Whitters became more determined to put herself in the spotlight, she repeatedly found herself shut out.

“I was taking a lot of label meetings last year, and I actually stopped, because I just felt very uninspired by what was happening with a lot of them,” says Whitters.

Instead of trying to mold herself to meet industry expectations, Whitters opted to start Pigasus Records, her own imprint in partnership with Big Loud Records and Songs & Daughters. The name is a nod to John Steinbeck, one of Whitters’ favorite authors, who used the emblem of a pig with wings as a symbol of his perseverance. Many people would see staying independent as a big risk, but Whitters saw it more as a means of survival.

“I’ve just had to blaze my own trail, I guess, because I’ve been told ‘No,’ or ‘That can’t exist,’ or ‘That’s not the way we do it,’ ” Whitters says. “In hindsight, I don’t think there’s any other way that I would have had it.”

While the pandemic continues and she’s unable to tour, Whitters is reconnecting with her roots — working on the farm, sipping coffee on her parents’ front porch, driving down the back roads of her town. All the while, she’s using her free time to embrace everything that comes her way and collect more stories.

“I’m not consciously sitting down with a pen and paper writing songs, but I think that I’m living and having conversations with people and people watching. In a way, I’m going to the well and finding inspiration by just living life.”

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