Lainey Wilson’s Ride Like a ‘Whirlwind’ Is Dazzling » PopMatters

Country artist Lainey Wilson had every reason to go far. In this Whirlwind year, though, she’s discovering what’s at the end of the rainbow.

Whirlwind Deluxe Lainey Wilson BBR Music Group / BMG Nashville 22 August 2025

Long before writing, recording, and performing songs with titles like “Call a Cowboy”, “Counting Chickens”, and “4×4×U”, Lainey Wilson embedded herself in a country-western kind of existence while growing up in the rural northeast Louisiana town of Baskin. 

Momma Michelle and Daddy Brian gave her and her sister Janna a proper upbringing down on the farm. Yet Lainey knew by the age of nine, as a sweet, starry-eyed kid called her first written song “Lucky Me”, what she wanted to do for a living and where she wanted to do it. Southern artists like Tim McGraw (who attended Northeastern Louisiana University just up the road in Monroe), Dolly Parton, Lee Ann Womack, and Vince Gill caught Wilson’s attention. 

At that same age, a family trip to Nashville to see country legends such as Bill Anderson, Crystal Gayle, and Little Jimmy Dickens perform at the Grand Ole Opry heightened her childhood dream. There was no going back when little Lainey told her folks: “This is home.”

For one thing, there were no stoplights in Baskin, then a town of 180 people, according to Lainey Wilson. Ten years later, after graduating high school, it was full speed ahead for 500 or so miles to the Music City. Of course, there were hardships for a youngster who didn’t start playing her father’s guitar until he accidentally handed it to his daughter. 

The only fellow Baskin native she knew upon arriving in Nashville was songwriter-producer Jerry Cupit, who became her mentor until he died in 2014 at the age of 60. Her first “home” was a 20-foot Flagstaff bumper-pool camper trailer in the parking lot of Cupit’s West Nashville recording studio. The rest of the story is Wilson’s history to tell, and she tells it well. Just days after the first anniversary release of Whirlwind, her fifth and most recent studio album, Wilson is in the middle of a world tour that allows the highly decorated artist to take her storytelling talents around the globe.

Huge venues are filled to the rafters or at near capacity, as seen in the 20,000-seat Ball Arena in Denver on 16 August. In the all-inclusive crowds are tiny tykes, tween princes and princesses, teens and prom queens, moms and dads, and gramps and grannies, all tickled to take in Wilson’s golden anecdotes as enthusiastically as she delivers them. 

This family-friendly production happened on a highly competitive night for music and sporting events in and around Denver, too. The Denver Broncos and Arizona Cardinals played preseason football at nearby Empower Field; the Colorado Rockies and Arizona Diamondbacks swung for the Coors Field fences; Wilco performed at Mission Ballroom; and My Morning Jacket concluded a two-night stand at Red Rocks. 

So many options. One clear choice. With an All-American cowgirl presence, a Hee Haw sense of humor that could make the late Buck Owens laugh again, the folksy twang of Reba McEntire, and a 22-song set list filled with toe-tapping hits, clever collaborations, and moving moments, Lainey Wilson has made country cool again.

Tilt-A-Whirlwind

Four songs into her show with a hard-charging, multitalented five-member backing band that was featured on occasion, Lainey Wilson put her electric sizzle on display with a fast-talking preacher’s passion during the first of several extended soliloquies. 

“Welcome to the Whirlwind World Tour, everybody!” she exclaimed. “I know it feels like life is a whirlwind a lot of times for all of us, y’all. Just try to keep one foot on the ground, but tonight we’re gonna celebrate it! We’re gonna embrace it! Y’all, we’re gonna have the time of our lives!” 

Not since watching personal pop-country favorites like Faith Hill (with husband Tim McGraw on their Soul2Soul tour) and Shania Twain when Ball Arena was known as Pepsi Center, have I seen such a forceful figure from this genre take command of an audience like Wilson did this night. 

A visually impressive stage setting included video screens depicting scenes and landscapes of the Old West, along with a giant horseshoe that put the Indianapolis Colts’ logo to shame. The long catwalk gave Wilson many opportunities to bond with the audience or turn them on musically. She also did an informal “meet-and-greet” on a stroll across both sides of the floor in the show’s second half, then signed autographs during the last song — “Heart Like a Truck” — before her disappearing act below the stage. With a cheerleader’s fervor, Wilson would provide instant energy boosts by commanding “put your hands together”, “crank it up”, and “take it up a notch”. 

Among 11 of the 14 Whirlwind songs performed, rambunctious numbers like “Hang Tight Honey”, “Bar in Baton Rouge”, “4×4×U” and, of course, “Country’s Cool Again”, the latter peaking with an explosive electric guitar riff, completed the mission. 

Blue collar must’ve caught a new wind /
Doggone, dadgum it, didn’t see that coming

Lyrics from Lainey Wilson’s “Country’s Cool Again”

While showing off her booming voice, Wilson also implored spectators “to pull out your cellphones” and “light ’em up for me” during “Watermelon Moonshine”, one of five set list selections from her 2022 album Bell Bottom Country.

Hugs and Cowboy Hats

She reached for the sky on the pretty “Somewhere Over Laredo”, a soaring nod to The Wizard of Oz’s “Over the Rainbow”. The recent single is among five new songs on the Whirlwind Deluxe edition (via BBR Music Group/BMG Nashville) that was released Friday (22 August). A few minutes later, Lainey Wilson set the tone with a precious segment she called “my favorite part of the night — I get to crown somebody Cowgirl of the Night”.

Her eye had been on a sign held in the audience by an Armed Forces veteran from Colorado Springs (identified later by Fox 21 News as Jilliann Culp).  The woman wearing a white cowboy hat was brought to the stage, revealing she was a cancer survivor in remission who “wasn’t sure I was going to be able to make it to this concert tonight”. 

After a few warm hugs, Wilson handed Culp a black cowboy hat that she promised to let her keep while also planning to provide a bigger one, since it was a kid’s size. “All you gotta do is repeat after me and you’re about to be Cowgirl of the Night,” Wilson offered. “Say, ‘I am beautiful’ (Culp repeats); I am smart. (repeats); I can do anything. (repeats); I am strong. (Culp says, “I am resilient.”) 

“Damn, right!” Lainey Wilson proclaimed, adding, “I am fearless! (repeats); and I am Cowgirl of the Night.” (Culp repeats, to roaring responses of approval.)

Country Love Story

That was only 40 minutes into the show, but even the ever-optimistic and confident performer probably couldn’t imagine experiencing moments of wonder like this a few years ago, recalling the days she was playing in front of “87 people in Alabama”. 

In the Hulu 2024 original doc Lainey Wilson: Bell Bottoms Country, which is still streaming, Wilson’s manager, Mandelyn Monchick of Red Light Management, also disclosed with a laugh that “nobody showed up” for Wilson’s first showcase at the Back Corner venue in the Nashville neighborhood of Germantown. The tables soon turned, though. Monchick pointed out that after the first headlining tour in 2023, “We went from clubs to arenas in a matter of six months, which is insane. It’s a testament to all the work she’s put in.”

Though that rise to fame was delayed, her down-to-business dynamic and sweet, sunny side sincerity make it apparent that Wilson is here to stay. 

Before playing tender ballad “Whiskey Colored Crayon”, which she called “one of my favorite story songs” from Whirlwind, Lainey Wilson provided more deep thoughts, saying, “Where I’m from, storytelling is a way of life. We live our lives just on the edges of our seats, just wanting to laugh and wanting to feel something. And sometimes it’s those stories that get better every single time that you hear them. It’s those stories that made me fall in love with country music.”

Pickin’ and Grinnin‘

Lainey Wilson brought out opening act Kaitlin Butts (introduced as the “Oklahoma queen”) for the Don Williams cover “Tulsa Time”. The tune, also popularized by Eric Clapton, was a cool highlight until it was interrupted when someone needed medical attention and the band temporarily left the stage. However, the two super troupers soon returned to sing one last verse a cappella, much to the delight of the crowd. Another supporting act, the singer-songwriter simply known as Ernest, later joined Wilson for a seat near the front of the catwalk to play acoustic guitar and sing the ballad “I Would if I Could” as a duet. There’s a story behind that, too.

“Fun fact about this song,” shared Ernest, called “one of the most talented people I’ve ever met and also one of the funniest” by Wilson. “Dean Dillon and Skip Ewing wrote this song about 30 years ago, and Dean Dillon is a legend. He’s written a ton of George Strait songs and (Keith) Whitley songs, and songs we grew up on. For whatever reason, this song never got cut, and it sat in a vault for 30-something years. Within the same week, Miss Lainey and I both discovered this song and decided we wanted to cut it separately, and so we were kind of fighting, going back and forth.” 

Quickly jumping in, Wilson added, “I said, ‘Well, fine, why don’t we do it together?’” (She released it as a single in December 2023, and the duet landed on Ernest’s sophomore album the following year.)

What followed was a cozy pickin’ and grinnin’ session up front, giving Wilson a chance to introduce her band members: Matt Nolan (drums, playing a washboard for this next tune); Tommy Scifres (bass); Kevin Nolan (piano, guitar); Aslan Freeman (bandleader, pedal steel and guitar); and Sav Madigan (fiddle, guitar, mandolin), an impressive singer-songwriter who also co-founded the Accidentals, a fine Americana band based in Michigan. 

“I would not be here doing this if I didn’t have these people up here on stage,” Lainey Wilson said before plunging into the plucky “Counting Chickens” (accompanied by appropriate sound effects). 

Wearing her trademark cowboy hat and blue/green tie-dyed bell-bottoms with a matching vest, Wilson also took the opportunity to show a couple of her band members some slick dance moves on the rousing rocker “Bell Bottoms Up”. Another crowd-pleaser off the Deluxe version, it was recorded at Abbey Road Studios and shares its name with the downtown Nashville bar/Cajun restaurant she opened in February. 

This leg of the tour is scheduled to conclude with a Wildflowers & Wild Horse show at T-Mobile Arena in Las Vegas on 7 December, followed by 2026 dates in New Zealand and Australia. 

More rays of radiance will undoubtedly follow. Honored multiple times by three music organizations since 2021, Wilson has seven Country Music Association awards, topped by Entertainer of the Year in 2023 (becoming the first woman to earn that title since Taylor Swift in 2009). Bell Bottom Country captured CMA’s and Academy of Country Music’s Album of the Year in 2023, then the Grammy for Best Country Album in 2024. Over two decades after her first visit to the Grand Ole Opry, she was inducted as a member of the institution’s esteemed group of artists on 7 June 2024. 

Awards and acclaim might mount as Wilson seeks other creative outlets. After finding an even wider audience (including myself) by making her acting debut in season five of Taylor Sheridan’s hit series Yellowstone in 2022 (putting “a face to my name” Is how she described it), Wilson is set to make her first feature film appearance in 2026. That’s when Reminders of Him, starring Bradley Whitford, Lauren Graham, and Maika Monroe, is scheduled to be released. Wilson seems like a natural fit to be cast in a sister-act project with lookalike Daisy Edgar-Jones, the enchanting English actress who played “the swamp girl” of fictional Barkley Cove, North Carolina, in the film Where the Crawdads Sing.  

For now, though, the focus is on Lainey Wilson’s infectious music and incredible fan base. Before she called it a night (and splendidly went 30 minutes past the planned 90-minute lovefest), one more earnest, gracious uplifting message was delivered. It was a parting salute by an inspirational and emotional influencer, overcome by the loud Denver crowd’s affirmation and acceptance. 

“Thank you, thank you, thank you for making my dreams come true right before my eyes,” Wilson gushed. “I am so humble. I am so grateful. Thank you from the bottom of my heart. For anybody here tonight who’s got a dream, I don’t care what it is, y’all, life is too short. Roll your sleeves up and do what you gotta do. When somebody tells you no, it ought to make you want it so much more. There’s nothing that can stop you. …

“When I was a little girl, this is what I was supposed to do,” she reiterated. “I’m so glad that that nine-year-old little girl was not completely crazy. I mean, she was pretty crazy, but not completely.” 

With four months left in 2025 and more crowds ready to fall crazy in love, it certainly isn’t Lainey Wilson’s first rodeo. After taking pride in being known as “the camper trailer girl” for so long, it’s time for another nickname and award. Who knows what Country’s Coolest Cowgirl of the Year will accomplish next.