Sometime around 2004, a fifteen-year-old singer known as Hailey Faith booked her first paying gig: a performance at Melsha’s Tap, a wood-panelled bar in the tiny town of Swisher, Iowa, which was filled, for the occasion, with supportive relatives and friends, nearly all of whom were well acquainted with both the singer and the songs she sang—nineties hits like “That’s What I Like About You,” by Trisha Yearwood, and “Should’ve Been a Cowboy,” by Toby Keith. Back then, Hailey’s plan was pretty straightforward: graduate from high school, move to Nashville, become a country-music star.
She is thirty-two now, having reclaimed her given last name and executed her plan: she is known—not just to her home-town supporters but also to a growing number of listeners—as Hailey Whitters, one of the most appealing country singers and songwriters working today. On a recent Friday afternoon, she returned to the Swisher bar, now called Black Squirrel Tap, looking a bit like a celebrity trying to go unnoticed: sunglasses, scuffed cowboy boots, pale jeans, and an oversized fleece jacket with an allover polar-bear print that could have been either a limited-edition designer drop or something scavenged from her grandmother’s closet. (It was the latter.) She ordered a Busch Light and asked the woman who served her, “Ready for tonight?”
It wasn’t clear if the woman knew who Whitters was, though just about everyone else in town seemed to. At a desiccated convenience store across the street, a sign in the window read “WELCOME HOME HAILEY WHITTERS!” Next door to that was the DanceMor Ballroom, a cavernous 1929 landmark where Whitters was playing a pair of sold-out shows. The shows were a big deal for both her and the Ballroom, which is large enough to hold almost the entire population of Swisher, about a thousand people, though it doesn’t have sufficient bathrooms for such a crowd—the owners had trucked in a row of portable toilets for the occasion. It was the final weekend of Whitters’s first-ever headlining tour, and a chance for her to spend some time in Iowa before going back on the road for the summer. To promote the Ballroom concerts, she had appeared that morning on the country station KHAK, up the road in Cedar Rapids. (“The music we play comes from Nashville, but our hearts are firmly rooted right here.”)
Whitters’s career began in earnest two years ago, when she released “The Dream,” a warm and bittersweet album about her musical trajectory thus far. The opening lines are “I’m twelve years into a ten-year town / I’m too far in to turn around,” and although she had been considering moving back to Iowa when she recorded the song, the album confirmed that she was on the right path, earning her critical acclaim, a major record deal, and some high-profile opening-act engagements. The follow-up, “Raised,” arrived earlier this year: a charming, playful, mischievous album about loving and leaving your home town.
Whitters grew up across the highway from Swisher, in a town called Shueyville, and she has four siblings who live in the area, mostly working for their father’s excavation-and-industrial-cleaning company. A different kind of country singer might have chosen to emphasize the hardships and the tedium of small-town life, but “Raised” is buoyant and sometimes sly. The song “Boys Back Home,” for instance, has lyrics that echo any number of paeans to “country” living, but Whitters delivers them with warmth and a raised eyebrow. “They’ll bail you out of a ditch or a bar / And they won’t be caught dead in no ee-lectric car,” she sings, making it clear that she knows and loves these guys without quite claiming that she’s one of them. Until recently, Whitters’s image was glamorous and sparkly, but, these days, working with the photographer and stylist Harper Smith, she has embraced a playful, exaggerated version of Midwestern chic: prairie dresses, a ribbon in her hair, and, during a recent festival appearance, a pair of full-coverage briefs with “CORN STAR” printed across the back.
The DanceMor engagement was both a local gig and a big production: a makeup artist came in from Nashville, a videographer arrived from Los Angeles, and executives at Whitters’s label flew to town and parked their party bus behind the venue, creating a proper backstage atmosphere. Before the show, Whitters talked about the decision to lean into her Iowa identity. Just before releasing “Raised,” she’d had second thoughts, she said, wondering, “Is this too Midwest?” She has spent enough time in Nashville to understand the value of a good story and a memorable persona: these things, along with her excellent songs, have helped spread her music beyond Nashville. (The music Web site BrooklynVegan recently included her on its list of “current country singers every indie fan needs to know.”) But Whitters has not yet won over the radio program directors without whom no country singer, no matter how critically acclaimed, can be considered a mainstream success.
That night, Whitters was introduced by the KHAK morning-show hosts, who go by Brain and Courtlin. Brain told the crowd that Whitters’s current single, a cheeky confection called “Everything She Ain’t,” had been streamed more than ten million times—perhaps a roundabout way of acknowledging that the song had not made it into heavy rotation on the KHAK airwaves. The crowd was friendly and enthusiastic, excited about Whitters in general, though evidently not familiar with her entire catalogue. Whitters got the audience’s attention with “Boys Back Home” and a handful of well-judged covers, including “Wide Open Spaces,” by the Dixie Chicks, now known as the Chicks, who are among her biggest influences. (If you search “Hailey Whitters” online, Google will suggest a follow-up question: “Is Hailey Whitters a Dixie Chick?” The answer is no, although not wholly for lack of trying.) The show’s climactic moment came before “Everything She Ain’t,” when Whitters said that executives at her label had recently “surprised” her with some good news: they were going to make a serious attempt to persuade radio stations to play her music. “This next song is my very first single for country radio,” she said. In that sense, her career is only just beginning.
Is something wrong with country radio? Many people think so—the stations’ enduring power makes them a frequent target of criticism, as does their stubborn refusal to play whatever songs the rest of us think they should be playing. In a new book called “Her Country,” the music journalist Marissa R. Moss notes that in recent decades country radio stations have played fewer songs by women than they did in the nineties, when the Chicks were dominant. (The Chicks’ string of country hits ended in 2003, when they were blacklisted for criticizing President Bush and the Iraq War.) Last year, for instance, the Top Ten songs on Billboard’s year-end Country Airplay chart were all by men. “Country music went from being synonymous with powerful women to truck-riding ‘bro country’ crooners,” Moss writes. Her book is about how a handful of women performers fought to change this. Some, like Miranda Lambert and, more recently, Maren Morris, found ways to make songs that radio couldn’t resist; others took a different approach. Kacey Musgraves built a fan base on her own, becoming a crossover success—in 2018, she released “Golden Hour,” which won the Grammy for Album of the Year—despite attracting only moderate interest from country-radio programmers. And Mickey Guyton, another of Moss’s subjects, is a Black country singer and songwriter who has earned some impressive distinctions (four Grammy nominations, a performance at the White House) without having had a proper country hit.
As a girl, Whitters never worried that there might not be a place for her in the country mainstream. She arrived in Nashville as a freshman at Belmont University, where she had enrolled in order to keep her parents happy, and to pass the time until she was discovered—she was sure it wouldn’t be long. In 2015, she independently released an album called “Black Sheep,” which is a bit moodier and more rock and roll than the music that she makes now. In the years that followed, she sharpened her approach, working with Jake Gear, a fellow-Iowan whom she met in Nashville. (Gear, who helped Whitters produce her subsequent albums, is the general manager of a Nashville publishing company, and also her fiancé.) Whitters’s rise was assisted by a cohort of women musicians, many of whose stories are told in Moss’s book. She wrote “Ten Year Town” with Brandy Clark, an accomplished Nashville songwriter who has lately emerged as a respected singer, too. Maren Morris posted about the song on Instagram, and then invited Whitters to be her opening act. The exposure helped get Whitters a deal with Songs & Daughters, a new imprint that was founded by the songwriter Nicolle Galyon in partnership with the powerful Nashville label Big Loud, in the hope of nurturing the careers of more women musicians, and maybe ultimately changing the male-to-female ratio on country radio.
Stacy Blythe, Big Loud’s senior vice-president of promotion, is in charge of airplay, a job that requires a mixture of optimism and pragmatism. In the months since the new Whitters album was released, Blythe and her colleagues have paid close attention to streaming data and other indicators, like the number of times people used the Shazam app to identify “Everything She Ain’t.” (It’s a good sign when listeners want to know more about the song they’re hearing.) The Highway, a satellite-radio country station, was early to add “Everything She Ain’t” to its rotation, and a few local stations played it, too, including WPAW, in Greensboro, North Carolina, and WKHX, in Atlanta. Blythe told me that these indicators helped persuade the label to embark on the slow and expensive process of formally soliciting program directors to add the song to their playlists on or before its “impact date,” June 27th. After that, stations can begin doing their own research, conducting polls in which listeners are asked to react to unlabelled snippets of the latest releases. By August, Blythe and her staff may have an idea of whether or not Whitters’s song will be a hit.
Moss, in her book, quotes a radio professional who explains his industry’s neglect of Kacey Musgraves by saying, “I haven’t felt a whole lot of connectivity with her.” Blythe’s aim is for stations to feel as if Whitters is paying attention to them; she might make her available for interviews and, if necessary, send her out to perform at radio-station concerts, at the label’s expense. Some record companies go further. All weekend, one of the most-played songs on KHAK was “Doin’ This,” which was on the way to No. 1. It’s a brawny and effective evocation of the troubadour’s life, by Luke Combs, currently one of the genre’s most reliable hitmakers. Listeners were invited to enter a contest for the chance to win a trip to Atlanta in July, to see Combs play a show at Mercedes-Benz Stadium, home of the Falcons. The prize included airfare for two, a hotel room, and five hundred dollars in spending money, and was sponsored, as the announcements disclosed, by Combs’s label, Sony Music Nashville.
Blythe says that she doesn’t worry about the difficulty of getting songs by women played on the radio. “There are so many more females on the chart than years ago,” she said. The week after Whitters took the stage in Iowa, “Never Wanted to Be That Girl,” a duet by Carly Pearce and Ashley McBryde, reached the top of the Country Airplay chart. The song updates the concept of “Jolene,” the Dolly Parton classic: in this version, there are two women, both victims, both of whom feel like the other woman. In April, a different duet went to No. 1: “Drunk (And I Don’t Wanna Go Home),” by Miranda Lambert and Elle King. These are the first duets by women to reach the top of a country chart since a song by Reba McEntire and Linda Davis managed it, in 1993. In this context, Whitters’s would-be hit doesn’t seem like such a long shot: it’s a cheerful, short song (two and a half minutes), with banjo and fiddle, about a girl telling a boy she can be “the whiskey in your soda / The lime to your Corona / Shotgun in your Tacoma.”
In country music, maybe more than in any other genre, there is no shame in giving audiences what they want. Saturday’s crowd at the Ballroom was louder and looser than Friday’s had been: at one point, people formed a circle around an older woman who was doing something like break dancing; it turned out to be Whitters’s aunt Tina, who is mentioned in one of her songs. (“We learned how to ration apple pie / And how to dirty dance, when Aunt Tina had too much wine.”) From the stage, Whitters announced a drinking game: “Drink every time I say ‘small town.’ ” And then she sang “Small Town,” by John Mellencamp. For an encore, she returned holding aloft a can of beer and said, “There’s no beer sweeter than a Busch Light.” She sang, “Let the big world spin all around / Beer tastes better in your home town,” as if she couldn’t imagine being anywhere else.
It would be easy to chuckle at the sight of a sharp singer-songwriter working so hard to be ingratiating. But one strength of the country-music industry is its ability to manufacture consensus, creating a shared ledger of hits—a musical blockchain, distributed among radio d.j.s and cover bands and everyday listeners. These are the country songs everyone seems to know: the ones that emanated from the KHAK tower, the ones that were performed by a local man on the back patio of the Black Squirrel on Saturday afternoon, the ones that inspired some impromptu dancing when they came on over the P.A. after Whitters’s Saturday-night set was finished. Country radio is not the only way to add a song to the blockchain. Mellencamp’s “Small Town,” for instance, did not receive significant country airplay in the nineteen-eighties, when it came out; it has been retroactively deemed a country classic. But country radio remains the surest way to reach the habitual but casual listeners who seem to form the bulk of the country audience. It’s an old-fashioned system and an obviously imperfect one, destined to overrate some songs and to underrate others. It may well also be unfair, although musical fairness is hard to define: by what metric does any song or singer deserve ubiquity or obscurity? But, deep in the streaming era, country radio retains its power. At one point during the weekend, Gear, Whitters’s fiancé, was considering how radio success might change her career. “If she had a Top Thirty hit, we’d be playing these all over the country,” he said, gesturing at the DanceMor Ballroom. That’s probably true—though it is true, too, that there are plenty of emerging or aspiring country singers, all across America, all thinking more or less the same thing. ♦
