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How Lainey Wilson Defied a Country Radio Stereotype En Route to CMA History

"These nominations serve as an endorsement... for her work as an artist, a songwriter, and a representative of the genre," says Mandelyn Monchick.

Earlier this week, BBR Music Group artist Lainey Wilson not only earned her very first CMA Awards nominations, but in her inaugural nomination year, she led the entire field with six nominations — and, in the process, joined Glen Campbell, Brad Paisley and Kacey Musgraves as the only artists to earn six or more CMA nominations in their first year on the ballot.

Wilson is nominated for album of the year (Sayin’ What I’m Thinkin’), song of the year (“Things a Man Oughta Know”), new artist of the year, female vocalist of the year, and picked up nods for music video and musical event of the year for “Never Say Never,” her collaboration with Cole Swindell.

“These nominations serve as an endorsement by the country music industry and community for her work as an artist, a songwriter, and a representative of the genre,” says Wilson’s manager, Red Light Management’s Mandelyn Monchick, adding that the nods “give us a big boost in our efforts to continue laying the ground work for her to fulfill her potential as a prodigious, historic artist and icon.

“We celebrated by toasting Dom Perignon at 8:30 a.m. with some of the team — then, back to work.”

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“Things a Man Oughta Know,” which Wilson wrote with Jonathan Singleton and Jason Nix, blends practical knowledge with emotional intelligence as she lists off a string of life lessons she’s learned, from fixing a tire to how to fight for the right relationship. Last year, the song became Wilson’s first No. 1 hit, and she followed with the swaggering Cole Swindell collaboration, “Never Say Never.”

In addition to notching two No. 1 hits, Wilson has been on the road opening shows for Jon Pardi, and it was recently announced that she will join Luke Combs on the road next year for his 2023 world tour. In between tour dates this summer, Wilson also began filming for a recurring acting role on the hit series Yellowstone. Wilson will release her new album, Bell Bottom Country, on Oct. 28, just weeks before she makes her acting debut on Yellowstone‘s fifth season, which premieres Nov. 13. These are all worthy milestones for Wilson and Monchick, longtime friends who have been working together in various capacities since 2015.

And they help Monchick earn the title of Billboard‘s Executive of the Week.

“I was working as an assistant for an entertainment attorney and began setting up writes for Lainey with some of the newly-published songwriter clients. We were friends and eventually roommates. I was just a fan of her music and became obsessed with getting everyone to understand how amazing and incredibly underrated Lainey Wilson was,” Monchick recalls. “What stood out to me first was her songwriting. She’s incredibly prolific and I’m a sucker for great lyrics and wordplay. The more I got to know her, I saw her unparalleled work ethic, her genuine nature, and her impressionable energy and entertainment chops. She’s a true entertainer on and off the stage. At some point along the way, I realized my dream was to help make and watch her dreams come true, and I don’t think it gets much better than that.”

Here, Monchick discusses the release strategy behind “Things a Man Oughta Know,” Wilson’s hit duet with Cole Swindell and new collaboration with HARDY (“Wait in the Truck”), her role on Yellowstone and more.

“Things a Man Oughta Know” was a huge breakthrough for Lainey. What key decision did you make that resulted in it topping the chart, especially in a climate that is difficult for female artists to earn a No. 1 country radio hit? 

The key decision was our commitment to show up, do the work and help put our team in a position to do their jobs to the best of their abilities. “Things A Man Oughta Know” went to radio in August of 2020 when everyone was just trying to figure out what to do to stay afloat and keep things moving forward. So we did whatever we could — from posting multiple TikToks per day, to hosting Instagram Live series with other artist friends, to opting in for whatever exposure opportunities came our way. The breakthrough was a result of Lainey’s commitment to hard work and her relentless tenacity, especially during a time where other folks were complacent or put their efforts on pause. She also has one of the best radio teams in the biz who matched her hard work and tenacity throughout the push to No. 1.

What was it like working with her label to release “Things A Man Oughta Know”? Were there any reservations on releasing it, given that it is a slower song? 

“Things A Man Oughta Know” raised its hand from the beginning when we released the first four tracks off Sayin’ What I’m Thinkin’, as an EP titled Redneck Hollywood in September of 2019. We felt the song was too slow to be the first radio single so we chose the mid-tempo “Dirty Looks,” which didn’t end up charting as well as we hoped. We debated going with the more uptempo “WWDD” [“What Would Dolly Do”] to follow “Dirty Looks,” but “Things A Man Oughta Know” kept raising its hand. So we followed the data, and our gut, and are very happy it defied the stereotype of a slow single by a female at country radio.

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How did having a breakthrough No. 1 hit, followed by a hit duet with “Never Say Never,” play into having Lainey recognized during awards time?

Each step has added another brick to the foundation. Getting a No. 1 as a new, authentically country female is tough, so when it happened, a lot of the music community felt like they earned that No. 1 song, too. And it truly did take a village. There were numerous messages from friends and fellow collaborators saying, “For those of us fighting the good fight, this win keeps us going.” To follow that with a hit collaboration with an artist that is as well respected and accomplished as Cole Swindell broadened Lainey’s network of support and raised awareness, legitimacy and belief that she was an artist with a high ceiling and long-term potential.

Lainey earned a two-week Country Airplay No. 1 with “Never Say Never” with Cole, and now she has a duet with HARDY on “Wait in the Truck.” How has she become a go-to collaborator, and how do you decide which collaborations are best? 

First, Cole having Lainey as his duet partner on “Never Say Never” gave her a significant nod of legitimacy to both the industry and fans. The success of the song proved that she was in fact a worthy, valuable feature. On top of that, Lainey just sells herself. She’s a great writer, performer, artist, person… just put her in a room with anyone in any situation and she’ll win them over. That’s part of the magic, but there’s no tricks. It’s all genuine. There’s a lot of collabs she’d like to do, but right now, we’re focusing on opportunities that come together organically, whether that be through a friendship or in the writing room, and serve a purpose in helping us take the next step toward the next goal. Lainey and HARDY have toured together, written together, and developed a friendship that has lead to an artistic chemistry conducive to what has proved to be a hugely impactful duet.

Lainey also has a recurring role coming up on Yellowstone. How did that opportunity come about? Also, a recurring acting role has a higher time requirement. What were those conversations like with Lainey in deciding to commit time to this? 

Lainey had her first sync in Yellowstone Season 2 Episode 1 with a song off her self-titled indie EP called “Workin’ Overtime.” This introduced Taylor Sheridan to her music, and led to an invitation for Lainey to perform at the finale of Sheridan’s The Last Cowboy “Run for a Million” competition in Vegas. Taylor and Lainey developed a friendship from there that led to a couple more syncs in Season 3 and eventually the offer for Lainey to inspire and play a musician character named Abby in the upcoming Season 5. Lainey has made a commitment to running through doors that open for her. The Yellowstone opportunity was no different. We didn’t really have a conversation on whether or not we should take him up on the offer — it was a no-brainer. We definitely learned the realities of the time commitment required of a recurring acting role, but it was completely worth the grind and lack of sleep to make it all work. Lainey has come to learn how much of a passion and knack she has for acting and plans for it to be an ongoing arm of her career.

She is gearing up for the release of Bell Bottom Country, and the project’s first single, “Heart Like a Truck,” is at No. 34 on Billboard‘s Country Airplay chart. There were two radio singles from Sayin’ What I’m Thinkin’. How did you decide now was the right time to release a new album? 

We recorded Sayin’ What I’m Thinkin’ in the spring of 2019, so she’s had quite a while to accumulate another pool of songs. We didn’t put a timeline on it, she just kept writing until we got to the point where we would listen through 15-20 demos and go, “I think we have a record.” That’s how we knew it was time. Plus, Sayin What Im Thinkin actually turned three years old in 2021, even though it was new to the rest of the world, so Lainey had more things she wanted to say and we needed the new music to support her development as a person and as an artist.