How Hailey Whitters Became Nashville’s Newest Unsigned Star
Hailey Whitters’ grandfather wasn’t a songwriter, but he had a way with words — and a sense of humor — that clearly runs in the family.
“My grandpa had a turf farm, and he called himself ‘the Grass Man,'” Whitters says, taking a swig of beer before standing up and showing off her oversized hand-me-down red jacket that reads, on the back, “Our Grass Is Legal.” Her grandmother found it in the basement and passed it on when she heard that Whitters had written a song inspired by the saying. “People in town started calling him to buy weed,” Whitters adds. “So he made that his business motto: Our Grass Is Legal.”
It’s late afternoon in East Nashville and the place is empty, with the only other noises the clinging of a bartender shifting glasses and some Velvet Underground playing on the speakers. Whitters, in white platform combat boots, that red jacket and black jeans, lives a few minutes away, and she came here a lot when she was working on her forthcoming LP, The Dream. Sometimes, she and her co-writers would sit and rehash songs they’d been chiseling earlier, slinging back Miller Lites. Other times, she just needed a spot to hide away from a town that can stifle and crush creativity just as easily as it nurtures it.
But lately, Whitters, 29, has been doing more celebrating than anything else: her two new songs, “Ten Year Town” and “The Days,” have been starting to gain some momentum on streaming playlists and, last night, she got word that she’ll be opening a few dates for Maren Morris in the fall. So she stayed up late, drank a little too much and ate a hot dog at another neighborhood bar. “[Morris] had posted about one of the songs I released, and so I sent her the record,” Whitters says. “She and I used to write together when she first came to town, though we haven’t been keeping up. But I sent her the record and my agent called soon after and said that Maren wanted me to come out on a few dates. I have no label, no manager, no nothing. So for her to do that was so ballsy. I’m just ecstatic.”
The song that Morris posted about was “Ten Year Town,” a devastatingly honest acoustic meditation on the heartbreak that comes with watching each year go by in pursuit of a dream that may or may not ever come true. Nashville’s colloquially known as a place where it takes a decade to “make it,” and Whitters has been here for 12 years, since she moved from Shueyville, Iowa, to attend Belmont University and be the first in her family to graduate from college. And there have been plenty of victories: a publishing deal with Carnival, cuts for Little Big Town, Alan Jackson and Martina McBride and an album, Black Sheep, in 2015. But there’s been a lot of disappointment too, watching the rapid rise of others as she worked tirelessly just to be heard.
“I need longer lashes and a shorter dress to be an overnight success,” she sings on “Ten Year Town,” co-written with Brandy Clark. “I thought this year I’d wear that crown, I’m twelve years into a ten year town.”
Nashville constantly sits on untapped goldmines of talent, including many songwriters who can take years, if it ever happens at all, to get their due. Some of the town’s most talented voices, like Lori McKenna, Natalie Hemby and Luke Dick, have spent ages clocking hits for others while waiting a decade or two into their careers, as is the case with Hemby, to release a solo project. For the space between mainstream country and indie Americana, there just isn’t a lot of room for artists like her or Whitters, who look to idols like Gillian Welch but also grew up listening to the Dixie Chicks on actual country radio, back when radio played those sorts of things.
“Growing up, I was hearing such perspective in songs,” Whitters says. “Hearing [Tim McGraw’s] ‘Red Ragtop,’ or [Alan Jackson’s] ‘Remember When,’ which is such a precious, vulnerable song. I feel like that’s what has always inspired me to write country music — it feels real, and it feels authentic to people’s experiences. Every once in a while we will get a ‘The House That Built Me,’ where everyone slows down for a minute and looks inward. That’s what I want to do with my music. I want to say things.”
Because Whitters wanted to be heard on the radio, she tried to write something she thought might better “fit in with what was happening” on the airwaves, only to toss it when it didn’t feel like her. An “expensive lesson,” she calls it. What came next was a period of deep frustration — reaching that 10-year mark in Nashville, with so much and so little to show for it.
“I was brokenhearted and tired two years ago,” she says. “I was a little lost and confused, and I feel like I found out who I was in that process. That’s when I spoke to [producer] Frank [Liddell], and he encouraged us to jump off the deep end and start making a record. And it was just the most beautiful year of daydreaming.”
Whitters turned off distractions like the incessant dings of social media and made the record with her boyfriend, Jake Gear (“He said, ‘Do you want a ring or a record?'” she recalls). She spent extended, intentionally aimless chunks of time in her backyard with her chickens, letting her mind roam, and mulled a lot on loss and mortality — eight years ago her brother died in a car accident, and she started to witness a transition in the ever-changing grief cycle.
“I could feel a shift to where I started noticing the beauty in things,” she says. “I’m always running towards the future or hung up on the past. But I slowed down and started looking around at the present moment and appreciating the little things.” Whitters channeled both beauty, pain and disappointment into The Dream, which features co-writes with McKenna, Hillary Lindsey, Nicolle Galyon, Jessie Joe Dillon and Waylon Payne, as well as a cut each from Brent Cobb and Chris Stapleton.
One song, “The Days,” written with Lindsey and Ben West, charts that feeling she experienced in her backyard: the need to take stock of the moment rather than constantly grabbing for something bigger or a future that inevitably blends into the past, delivered in her frank and potent farmland twang. “Instead of counting up the days,” she sings, “I just want to make them count.” It wasn’t easy to get there, but she’s finally found her motto.
“It comes back to the country music I was raised on,” she says before heading home to work on songs and tend to the chickens. “It wasn’t about trucks and tailgates and hooking up. It was about life.”