Lainey Wilson was ‘too country’ for Nashville. They’ve wised up. (2024)

The comment stuck as Wilson increasingly realized that to climb country’s ladder, especially as a woman, it was essential to stand out beyond powerful vocals and clever lyrics. So, she embraced a signature aesthetic of bell-bottoms and wide-brimmed hats — an instantly recognizable silhouette that, as she likes to say, invokes country music with a “flare.”

“In the beginning, I was like, ‘These folks aren’t going to remember my music. They’re not going to remember the way that I sing or my songwriting. But they might remember how I make them feel,’” Wilson said, sitting in her dressing room in late October before performing to a sold-out crowd at Nashville Municipal Auditorium, where she was the opening act for her good friend Hardy. These days, fans tell her that seeing her distinct style motivates them to highlight their own: “I hear a lot of people say that they feel inspired to step outside the box and do things that are a little different and express themselves in different ways.”

Wilson, 31, has always been considered “a little different” from her fellow contemporary country singers since she moved to Nashville more than a decade ago, setting up shop in a camper trailer outside a recording studio that belonged a family friend who owed her grandfather a favor. Fresh from a life growing up on a farm, and armed with a Louisiana twang and years of playing guitar and singing in venues across the South, Wilson was ready for country music — but country music was definitely not ready for her.

Her common refrain is she was “too country for country,” as she arrived when the format was consumed with trendy, pop-centric hits about bros driving with girls in cutoff jeans riding shotgun in pickup trucks. The genre’s gatekeepers weren’t interested in a young woman’s perspective on small towns and heartbreak and, as Wilson sang on an early independent album, how “life is tough, but this girl’s tougher.”

“I knew that it was all about timing. I did. I was like, ‘The truth is, what I do now is not cool,’” Wilson said. “But everything goes in style and comes out and goes back in and comes out again. That’s just how life works.”

When the pieces suddenly fell into place, the speed took Wilson by surprise. She’s suddenly reached some of the highest levels of success — five consecutive No. 1 hits on country radio, sold-out tour stops, hundreds of millions of streams, a role on the enormously popular Western drama “Yellowstone.” On Nov. 8, she’s up for entertainer of the year at the Country Music Association Awards, the highest honor at the genre’s most prestigious award show. She’s nominated alongside superstars Morgan Wallen, Carrie Underwood, Chris Stapleton and the category’s two-time reigning champion, Luke Combs, a longtime friend who invited her along as an opening act this year on his stadium tour.

Wilson watched the nomination announcement at her house in Nashville, where she spends very little time because she’s always on the road, and she had a feeling it would be a big morning. In 2022, the first time she was eligible for the CMAs, she was the most-nominated artist. This year, she repeated the feat again with a whopping nine nominations, including album of the year for her latest record “Bell Bottom Country”; she appears twice in both the song and single of the year categories for the yearning “Heart Like a Truck” and the murder ballad “Wait in the Truck,” a duet with Hardy.

The entertainer nod was a shock — and honestly, extremely satisfying. Not only is it an official stamp of approval from her industry mentors and idols, but she watched for years as her male contemporaries — some of whom moved to town after she did — landed record deals and started selling out tours. Now it’s her turn.

“I laugh and joke with all of my guy friends in the industry, I have for years: ‘I’m coming for you,’” Wilson said, smiling and glittering in her shiny gold bell-bottoms. “And it kind of feels that way. I’m like, ‘We’re here.’”

When you’re told “no” over and over, the initial victories come as a shock. Songwriter Trannie Anderson, who has written with Wilson for years, recalls the elation in spring 2022 when Wilson stunned the audience at the Academy of Country Music Awards, winning song of the year for her breakout single “Things a Man Oughta Know” and beating megahits such as Wallen’s “7 Summers,” Walker Hayes’s “Fancy Like” and Jordan Davis and Luke Bryan’s “Buy Dirt.”

Wilson took the stage in disbelief, telling the crowd, “Country music is my life. It’s been my life for as long as I can remember. … Oh my gosh, y’all.” The following day, without missing a beat, she flew to Arizona to spend a week co-writing songs for her next album.

“After being onstage on national television in front of everybody and having the biggest night of her life, she would not stop. She wanted to write 10 songs the first day,” Anderson said. “I feel like most people need to take a breath and, like, take a week off. And she was already on to the next thing. … She’s just a machine.”

Wilson said she was one of those kids who always knew exactly what she wanted to do, ever since a family trip to the Grand Ole Opry at age 9: “I felt at home even then.” She started writing songs and playing guitar in her tiny hometown of Baskin, La., and sharpened her singing skills with a job in high school as a Hannah Montana impersonator, where she traveled between preschool birthday parties and nursing homes, an unexpectedly helpful lesson in adjusting your performance to your audience.

Making the jump to Nashville in 2011 was challenging. She paid the bills by singing in bars around Louisiana, Arkansas and Mississippi, knowing she had to meet fellow songwriters, get a publishing deal and then a record deal, release an album and get a song on the radio. She just didn’t know how to make any of that happen.

“We didn’t have any strings we could pull or crazy connections when we were coming up. It was like, you know, ‘Hey, I’m friends with this person, and they’re this person’s assistant. And they like you, so maybe they’ll talk about you to their boss,’” said Mandelyn Monchick, her manager. Monchick met Wilson in 2015 and couldn’t believe that no one was paying attention. She heard one of Wilson’s early songs, the vulnerable “Dreamcatcher,” (“I’ll be your shelter in the rain, and a shooting star to take your pain, the common heat of a burning flame”) and thought her music was “next level.”

Wilson and Monchick put together a songwriter showcase and no one showed up; they tried to get industry gatekeepers interested and nothing clicked. The “too country” criticism remained a roadblock — executives didn’t “get” her, and some wondered whether her Southern twang was even real. People back in Baskin started asking Wilson when she was going to move back home and become a teacher already.

“Sometimes doors were slammed in my face and my feelings got hurt, but that didn’t mean I was hanging it up,” Wilson said. “I was going to keep on going.”

Eventually, a bro-country backlash began, and listeners started craving a more traditional country sound. Chris Stapleton swept the 2015 CMAs, signaling the industry felt the same way. Wilson landed a publishing deal in 2017 after independently releasing music, and a year later, signed with Broken Bow Records. Influential executives started to champion her.

“It’s a very emotion-driven, opinion-driven business,” Monchick said. “You have got to get that first person to care. And there were a few key people that just liked her.”

One critical person was Paramount Network’s “Yellowstone” creator Taylor Sheridan, who became a fan and featured some of her songs on the show starting in 2019 — and would eventually offer her a small role in the fifth season. Country radio programmers were experiencing serious “Zoom fatigue” in the midst of the pandemic, Monchick said, and they had little interest in new artists, but they found Wilson’s “Yellowstone” connection intriguing. (Wilson could not discuss the show, due to the SAG-AFTRA strike rules.)

Programmers started playing “Things a Man Oughta Know,” Wilson’s song that informs men she can change her own tires and catch her own fish, thank you very much, so they should focus on treating women with respect. In August 2021, it became her first No. 1 single, making her one of two solo female country artists to top the Billboard airplay chart that year.

Monchick thinks Wilson’s well-known years of trying to break through are partly why so many in the industry are invested in and thrilled by Wilson’s success. They know how hard she worked, and how long it took, and feel like they helped in some way.

“It was very grass roots,” Monchick said. So now, all of those people are rooting for her.

Even if you’re not a country music fan, there’s another reason you might have heard of Wilson: That TikTok. Last December, a TikTok user posted a video of Wilson singing “Things a Man Oughta Know” at a concert in North Carolina, and her leopard-print bell-bottoms showcased her backside in a way that fans found very appealing.

The video went mega-viral and briefly catapulted Wilson to a new level of internet fame. No, she can’t really believe it either. But everything in her life was becoming surreal at that point, so she joined in the jokes on TikTok. This summer, she and Lauren Alaina teamed up for a song called “Thicc as Thieves” that samples Luke Bryan’s “Country Girl (Shake It For Me)” and serves as a sort of countrified version of Sir Mix-a-Lot’s “Baby Got Back.” (“Oh my gosh, Lainey, look at your butt … how’d you get them bell-bottoms yanked up?!” Alaina banters at the end.)

“It was kind of me just making fun of myself, you know? Why not?” Wilson said, shaking her head. “Everybody else was making fun of it. Laugh with them.”

It showed a lighter side to her personality for fans who knew Wilson for songs about darker topics. “Wait in the Truck,” her duet with Hardy, is sung from the perspectives of a woman who was abused and the man who kills her abuser and goes to jail. Some in Wilson’s circle found the song topically upsetting, but she didn’t care. She wanted abusers to feel “haunted” by the song, she said, and show support to victims of domestic violence.

“I knew that even if radio never played it, that I had to be a part of it,” she said.

It went No. 1 and climbed the charts around the same time as her other “truck” song, the No. 1 solo smash “Heart Like a Truck.” Wilson wrote the track in 2020 with Anderson and Dallas Wilson (no relation); the trio call themselves “The Heart Wranglers.” Dallas Wilson recalled initially, they started writing a song that was “super up-tempo and fun,” but given the overall mood of the pandemic, they switched tactics.

“Lainey was like, ‘I think we need to write a little more real with where we’re at right now.’ And I’m so glad she did,” Dallas Wilson said. Instead, the song turned into a metaphor about how even when you feel like a beat-up old truck being dragged through the mud, you can persevere. “As a songwriter, she just really knows who she is and what she wants to say.”

Wilson’s fans point to this as one reason they connect with her so much — she just seems real. She tries to maintain privacy on some levels (she didn’t publicly reveal she was dating Devlin “Duck” Hodges, former Pittsburgh Steelers backup quarterback, until this May, more than two years into their relationship) but is also open about her struggles.

“The truth is my life ain’t perfect, and I want to share that with people,” Wilson said. “We all go through things, and some things harder than others. But it’s my job to make sure that people feel like they’re not alone.”

When Wilson opened for Hardy at Nashville Municipal Auditorium over three nights, she saw girls dressed like her, in bell-bottoms and wide-brimmed hats. “Every single morning … you get up and you look at yourself in the mirror and you tell yourself, ‘I am beautiful, I am talented, I am smart, I am godly, I am fearless,’” Wilson instructed the fans, before breaking into her song called “Atta Girl.”

She invited fellow breakout star Jelly Roll onstage to sing their duet “Save Me,” a tale of addiction that is in the top 10 on country radio charts. She sang her recent three-week No. 1 “Watermelon Moonshine,” a ballad reminiscent of Deana Carter’s “Strawberry Wine,” one of the ’90s country classics that helped shape her love of the format.

While country music has been in the headlines lately for its political and social divides, which can surface at award shows, Wilson remains on everyone’s side: “I’m friends with people from different sides of everything, and everybody shows me nothing but love and support,” she said. “I do the same right back to them.” She wants her music to bring people together. Fittingly, as Wilson embarks on new music that she’ll start recording in the new year, she’s already named the kickoff song and tour that will guide her next chapter: It’s called “Country’s Cool Again.”