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Hailey Whitters’ Day in the Sun Finally Arrives

Her watershed EP, The Days, tracks a decade of Nashville dream chasing...

Written by Chris Parton
Hailey Whitters’ Day in the Sun Finally Arrives
Hailey Whitters; Photo credit: Harper Smith

Back in late 2017,  singer-songwriter Hailey Whitters was in a bad spot. Twelve years into chasing her country music dreams in a city where it supposedly takes 10, she had just scrapped a project aimed at “commercial viability” – which deep down, she knew would never have fed her soul – and she was running out of options. She seriously considered heading home to Iowa and leaving the dream behind, but then something clicked.

“I hit my fuck-it point,” she says matter-of-factly, seated now in a sunny coffee shop near her East Nashville home. Looking supremely confident in a vintage T-shirt, jean jacket and big sunglasses, that “fuck-it point” was actually just what she needed, turning her fortunes upside down. She’ll leave here and head to a photo shoot for her watershed EP, The Days (out September 13)the first half of a brilliantly raw and insightful album titled The Dream, likely destined as a sleeper pick for best-of lists in 2020 – and then she’ll hit the road with Maren Morris for the fall leg of her Girl: The World Tour.

The dream is finally coming true, it seems, but it might not have if she’d kept going along as always.

“I just took a look at where I was and why I was doing this, and realized I’d been so tunnel-vision on my career that I was missing out on a lot,” explains Whitters, who until recently was just another talented-but-underappreciated artist toiling away in Nashville’s underground. “So this past year I kind of tuned out Music Row, decided I wanted to make a record on my own terms and just started making some life. For me it was this great year of exactly what the record is – realizing what the dream means to me.”

After arriving in Nashville in the mid-2000s, Whitters’ dreams weren’t totally unrealized. She scored a songwriting deal with Carnival music early on and penned a few acclaimed tracks for stars like Little Big Town (“Happy People”), Alan Jackson (“The Older I Get”) and Martina McBride (“The Real Thing”). All along she’s been working with the city’s elite tunesmiths and even released a well-received album titled Black Sheep in 2015. But for a girl who grew up listening to country radio, a little mainstream recognition would have gone a long way.

Fast forward to her “fuck-it point” and the decision to go down swinging, and everything changed. She wrote a song detailing her struggle with Brandy Clark titled “Ten Year Town” – a triumph of existential dread which rings true to any chaser of dreams – and then took a trip to Boston to write with Grammy winner Lori McKenna, returning home with two more songs that set the album in motion. “It was like ‘OK, I know what this record is. It’s gonna be called The Dream, and this is the concept.’” she says. “It all fell into place really organically, and it was just exactly what I was going through.”

“Ten Year Town” was quickly noticed after Whitters posted it online, finally turning heads as a sharp-eyed, sharp-tongued insight into what it’s like for women trying to break through in country music. With it’s soft acoustic sound and the reluctant tone of resigned defeat, it rang around the community not as a swan song, but as a rally cry, and became the album’s opening track.

“I knew we had to start with that song, because that’s the broken point that I was in when this record started coming together,” Whitters explains. “The broken spot is what led me to the whole journey of realizing what the dream meant to me. I realized I can’t rely on Nashville to make me happy.”

Detailing the bitter taste of holding out hope while also getting overlooked in favor of girls with bigger lashes and shorter dresses, the track was a “timing is everything” moment, arriving amid the ongoing debate over country’s gender diversity issues. And importantly, it introduced Whitters as an artist with something to say … a self-evident conclusion on The Days.

Moving on from that broken moment, the EP features all the optimism of her newfound point of view – plus a lump-in-your-throat message tied to the passing of time – all presented as a pristine-but-unpretentious throwback to country’s confessional roots.

“The Days” is a lovely, pure-country siren call asking listeners to soak up each moment as it comes, since you’ll never get them back. She stops wishing for a bad relationship to get better on “Dream, Girl,” gets stood-up and self-medicated on “Red Wine & Blue” and offers a vivid portrayal of the drunken, against-your-better-judgement feel of falling in love in “Loose Strings.”

The full album expands with six more literary-quality vignettes, but the cleverly titled “Heartland” may be the project’s natural conclusion – at least emotionally. Feeling like the well-adjusted counterpoint to “Ten Year Town,” it’s a sunset-country anthem dedicated to letting your “heart land” where it may – since Whitters was still questioning whether she was meant to be in Nashville or Iowa.

Now she’s got the best of both worlds. More at home in Nashville as she finds her artistic voice, Whitters will also be heading home physically this fall. She’ll open 10 massive shows for Morris – including one in Des Moines this month, not far from where she grew up – and the following night she and her band will travel to her actual hometown of Swisher to headline the tiny Dancemor Ballroom. It’s where her parents hung out in high school, and the kind of place that would close in the summer with a “gone fishin’” sign on the door.

The homecoming moment will be a triumphant one for Whitters, who will follow up with 14 more opening dates for Americana standout Brent Cobb. And she credits Morris for much of her current situation – saying the superstar helped reignite her passion by calling out “Ten Year Town” on social media.

“I’m gonna tell her this someday, but that lit a fire in my soul again,” Whitters says. “I had been looking for the magic of making music again, and I think that did it for me.”

Now, with the music she’s always wanted to make, plus a new co-management deal and perhaps more good news in the near future, Whitters’ dreams are closer than ever to reality. She’s grateful and resisting the urge to ignore this moment in pursuit of the next – but there’s still one more thing she can’t help wishing for.

“If there’s room for my music on country radio, I would love to be there,” she admits, finishing up our coffeehouse conversation. “I still haven’t given up on that dream, and I still think there is a place for it. … Not to quote my own song, but it’s kind of like that line in ‘Ten Year Town’ — ‘I didn’t come this far to only go this far.’”

Hailey Whitters The Days EP is out September 13, and The Dream is expected early next year.