A few days after accepting the award for new female artist of the year at the Academy of Country Music (ACM) Awards in Nashville this May, Hailey Whitters was onstage in Madison, Wis., opening for Shania Twain. Afterward, as she watched the legend from the wings, Whitters, 33, flashed back to her 8-year-old self “singing Shania Twain in [my] underwear in the living room … and it hit me just how far I’ve come,” she says. “I set out to do this, and I definitely was hellbent on achieving it, but even the last few months have surprised me.”
Her spring accomplishments also included a headlining club tour and landing her first top 20 hit at country radio. The winsome, effervescent “Everything She Ain’t,” released in early 2022, has spent 62 weeks on Billboard’s Country Airplay chart, peaking at No. 17 in June more than a year after its debut. In May, the song gave Whitters her first appearance on the Hot 100 chart.
Whitters experienced plenty of discouraging moments — when she wondered if she should head back home to Shueyville, Iowa, and its population of 700 — following her post-high school move to Nashville in 2007. But as she sang on her 2019 track, “Ten Year Town,” about trying to make it in country music: “I didn’t come this far to only go this far.”
Raised on ‘90s country and artists like The Chicks and Trisha Yearwood, Whitters knew that she wanted to move to Nashville after she and her mom attended the Grand Ole Opry during a visit to Music City when she was 15. During her early years in Nashville, she made inroads as a songwriter, landing cuts with big names including Alan Jackson, Martina McBride and Little Big Town. But her career as an artist was floundering, even after releasing her debut album, Black Sheep, through her music publishing company, Carnival Music, in 2015.
Yet the tide began to turn when she posted “Ten Year Town” on Instagram in July 2019. Almost immediately, artists including Maren Morris, Brothers Osborne and Carly Pearce supported the song. “They posted about it and it started generating all this buzz,” Whitters says.
Within two weeks, Morris had asked Whitters to open on her fall tour, a fortuitous move Whitters still can’t believe. “I had no label, no management,” Whitters says (her booking agency CAA relayed the good news). “It was pretty ballsy of her to ask, essentially, this no-name songwriter to open this massive tour. I quit my waitressing job right before the tour started.”
With excitement about Whitters renewed, she also found management: Make Wake’s Chris Kappy, whose clients include Luke Combs and Range Media Partners’ Matt Graham, who co-manages Midland, among others. The friends were both so enthusiastic about Whitters, they decided to partner.
“ ‘Ten Year Town’ brought me to tears. It made me really want to help her,” Graham says. “I met her at a bar in Nashville and called Kappy afterwards and said, ‘That’s a person that I would want to drink a beer with all over the world.’”
Whitters had opened three shows for Combs years before, and though Kappy admits he doesn’t recall the gigs, Whitters always remembered how well he had treated her. “She said, ‘You took care of me, and I was nobody,’” he reflects. “I heard the music, I fell in love with it, and then by just being a good human being ended up winning the business.”
In February 2020, Whitters self-released her The Dream EP on her own Pigasus Records. A few weeks later, she played a sold-out show at Nashville’s prestigious Exit/In with hit songwriter Nicolle Galyon and Big Loud CEO Seth England, among other label executives, in attendance. Galyon offered her a deal on her new Songs & Daughters label, a partnership with Big Loud Records, and Whitters believed she was finally making headway. Then the pandemic hit. “It felt like all the stars were aligning, and by that Friday, the world shuts down,” she recalls.
During the early months of the pandemic, she focused on songwriting, including Alicia Keys and Brandi Carlile’s 2020 song, “A Beautiful Noise,” for which she received a song of the year Grammy nomination. She also released a deluxe edition of Dream, called Living the Dream, that included collaborations with artists including Yearwood, Jordan Davis and Little Big Town.
Concurrently with focusing on her music, she revamped her look from jeans and t-shirts. Graham paired her with photographer-turned-creative director Harper Smith, and “it really shifted everything about how Hailey conveyed herself to her audience,” he says. “It captured the Midwest earnestness, cuteness, small-town aesthetic that Hailey really wanted to own,” as she leaned into pastel colors, florals, ruffles and hair bows.
By 2021, Whitters was eager to reemerge following months of Zoom co-writes. She had her first in-person writing session with Bryan Simpson and Ryan Tyndell at Tyndell’s studio on Music Row and left with a hit.
Simpson and Tyndell were working on a song with a “stark, moody, Spaghetti Western vibe,” Whitters recalls, but getting nowhere. She suggested they switch to something lighter. “I had that hook, ‘I’m everything she is and everything she ain’t,’ and we were off to the races.” Less than 90 minutes later, they finished “Everything She Ain’t,” and that night, Whitters sang it a capella to her producer boyfriend (now husband) Jake Gear, who replied, “We have to record that, like, instantly,” she recalls.
Her label had the same positive reaction. Though she had already finished recording songs for her 2022 album Raised, once Galyon and England heard the eventual breakout hit, Whitters says, “They just lit up and were like, ‘We have to release this.’ I was totally shocked. I thought we were done.”
When the album arrived — complete with the last-minute addition — digital service providers including Spotify, Amazon, Apple and Pandora embraced the song. TikTok also played a role in its success. “My philosophy has always been, ‘Don’t sign stuff that’s working on TikTok, sign great artists and help them crack the code on TikTok,’” Graham says. “Interesting pockets of TikTok connected with that record, like farm boys that really took to the song and ran with it.”
When the song reached a million streams a week, Kappy says Big Loud decided it was time to go to terrestrial radio with Whitters for the first time. The slow, steady climb has been propelled by “creating moments for the fans to fall in love with her,” he says, including opening for Jon Pardi last year and Twain this year, plus her ACM Award win, which was voted on by peers.
As Kappy sees it, “I think Nashville finally gave her that kiss that said, ‘Hailey, we know you’ve been here and we love you. You’ve earned this.’”