Lainey Wilson showcased her progression into one of country music’s foremost entertainers during the opening concert of her headlining Country’s Cool Again tour on Friday night (May 31) at Nashville’s Ascend Amphitheater (the first of two nights at the venue). Wilson, the reigning entertainer of the year at both the ACM Awards and the CMA Awards, and one of country music’s hardest-working artists, proved just why she’s worthy of those accolades during her headlining show.

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She also made good on the tour’s namesake declaration, welcoming two openers whose sets were steeped in twang, fiddle and steel guitar. Zach Top sailed through a solid lineup of songs with a decidedly ’90s country influence including “I Never Lie,” “There’s the Sun” and his album’s title track, “Cold Beer and Country Music.” Like country stalwarts Alan Jackson and George Strait, Top remained close to the center stage mic for the bulk of the performance, acoustic guitar in hand and letting the music flow into the open evening. Ian Munsick brought “the West to the rest” with his high-energy set that celebrated imagery of his Wyoming roots, melding in lyrics of tumbleweeds, cattle, and open ranges. His opening music was Eddy Arnold’s “Cattle Call.”

“It’s official — country’s cool again,” he told the Nashville crowd, as he sailed through “I See Country Everywhere,” “More Than Me,” and the Cody Johnson collab “Long Live Cowgirls” (sans the Texan hitmaker). He highlighted his Rocky Mountain Fever Band, which was clad in turquoise shirts and bolo ties, as they ripped it up playing songs including Ricky Skaggs’ “Country Boy” and offering up a searing fiddle on a version of Alabama’s “Fiddle in the Band.” He offered up a new song, “Heartbreak King,” before playing the fan favorite, “Cows–t,” as well as the namesake from a recent album, “White Buffalo,” and “Horses are Faster.”

When Wilson took the stage just minutes after 9 p.m., it was clear that she was intent on showcasing just why she’s been lauded with entertainer-level accolades of late, blending high-quality production, country songs with heart and an edge, and a high-energy persona that’s still down-to-earth.

The show’s production made top-tier use of two of her truck-themed hits, “Heart Like a Truck” and the HARDY collaboration “Wait in the Truck,” by showcasing a red, rotating, retro truck center stage throughout the show.

Clad in her signature bell bottoms, Wilson first appeared on top of the truck as she belted out “Straight Up Sideways” and “Smell Like Smoke.” She sang “Heart Like a Truck” while screens focused on Wilson as she sang from inside the retro auto,” while she performed “Watermelon Moonshine” seated on the truck’s tailgate.

Throughout the evening came across as not only an entertainer whose songs chronicle stories of love, ambition, and loyalty to home — but a mentor, aspirational role model, and the best friend who can be both supportive and give a motivating kick in the rear when needed. It’s clear the audience has responded — the crowd was filled with crowd members paying homage to Wilson’s signature style by wearing hats, sparkly bell bottoms and flared jeans.

“I’m not going to lie ya’ll, lately life has been a whirlwind,” she told the crowd. “That’s the world that I keep using, the word that keeps coming to my mind, out of my mouth, trying to keep one foot on the ground. We have literally been everywhere… with all the craziness, I will say, I have fought like hell to keep one foot on the ground and that’s been hard at times. I know a lot of y’all have been here from the beginning and I have a lot of people in my life who remind me who I am and where I come from and I know no matter where I go, no matter what I do, no matter where this job takes me, I’m always gonna be me, I’m always gonna know who I am right in here. I’m always going to find my way back home,” she said, launching into “Good Horses Come Home.”

During the sassy “Bell Bottoms Up,” she nodded to her growing empire as an entertainer — her new Lainey Wilson’s Bell Bottoms Up bar in Nashville, which opened that same day.

While Wilson’s openers for the evening were two traditional country-leaning male performers, Wilson’s guests during her headlining set were two ’90s hitmakers that Wilson called mentors and friends during her set — Terri Clark and Wynonna Judd. Judd teamed with Wilson to perform a rendition of Tom Petty’s “Refugee,” from the upcoming tribute album Petty Country. Wilson’s piercing soprano was a stellar match for Wynonna’s bluesy growl, making for a show-stopping moment of clear friendship and respect between the two performers.

“I can’t believe I’m on stage with Wynonna,” Wilson told the crowd, while Wy replied, “I’d open for you any day.”

Meanwhile, Clark teamed with Wilson to perform Clark’s 1996 hit “Poor, Poor Pitiful Me” from her new album Take Two, with Wilson playing cowbell.

Wilson often spoke of her Louisiana roots, while her intro music included Creedence Clearwater Revival’s “Born on the Bayou.” “My heart is filled with gratitude,” she told fans at one point, adding, “Tonight let’s be proud of where we are from and fired up about where we’re going!”

Wilson’s set blended music, theatrics, homespun stories and almost spiritual-minded words of encouragement throughout the evening, as she regularly related to and lifted up her “Wildhorses,” as she affectionately calls her fans. At one point, she crowned one concertgoer Cowgirl of the Night, but not before leading her — and the rest of the crowd — in lifting themselves up with affirmations including “I am smart. I am talented. I am beautiful.”

Wilson also offered up a medley of cover songs — but keeping in line with the tour’s name, instead of a lineup of rock covers, she paid homage to her inspirations with a medley of classic country songs, including Hank Williams’ “Hey, Good Lookin’,” Loretta Lynn’s “You Ain’t Woman Enough,” Johnny Paycheck’s “Take This Job and Shove It,” Randy Travis’s “Forever and Ever, Amen,” Reba McEntire’s “The Night the Lights Went Out in Georgia,” Miranda Lambert’s “Kerosene,” Alan Jackson’s “Gone Country” and her own “Country’s Cool Again.”

Though none of her bevvy of hit collaborators Jelly Roll, HARDY or Cole Swindell were surprise guests, Wilson did those songs justice, seated on the tailgate of the truck and offering acoustic versions “of the songs “Never Say Never,” “Wait in the Truck” and “Save Me,” with the latter song in particular turning into a redemptive, soul-cleansing crowd singalong.

From there, Wilson showcased a song, “4x4xYou,” from her upcoming August album Whirlwind, a song she noted is inspired by her beau Devlin Hodges.

The show concluded with “Wildflowers and Wild Horses,” as rainy, hurricane-themed imagery swirled on the screens behind Wilson as she stood atop the truck, belting out the empowering song that touched on her familial legacy of “five generations of blazin’ a trail.” In the final moments of the show, she stood tall, lowered her cowboy hat and raised one arm in the air. It’s a confident power stance used by so many headlining male country entertainers — but one that entertainer of the year winner Wilson now claims for her own.