With the smell of BBQ permeating through the balmy July air, Chris Young took the stage at Windy City Smokeout in Chicago on Friday (July 12) ready and willing to stir things up a bit.

“I have a feeling I’m going to go over my time tonight,” Young told the 14,000-plus crowd that had assembled on the hot tar parking lot of the United Center hours before just for the chance to take in all that the multi-platinum entertainer has evolved into. “I’m throwing some curveballs tonight in this set list.”

Indeed, the “Raised on Country” hitmaker seemed poised to keep things interesting right from the start, opening with “Hangin’ On,” “Getting’ You Home” and “Lonely Eyes” before taking the time to reminisce a bit.

“I was here when Windy City Smokeout was just getting started, so to see this, well, this is nuts,” Young said as the Chicago skyline stood tall behind him and thousands of adoring fans stood in front of him.

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From there, he tore into songs that quickly turned into singalongs — “Losing Sleep” and “Who I Am With You.” And yes, one couldn’t help but notice Young’s traditional roots showing throughout the night, even taking a moment between verses of his cover of “I’d Love to Lay You Down” for a little friendly advice for the crowd.

“Do you know who Conway Twitty is?” he asked inquisitively. “If you don’t, download some Conway Twitty tonight.”

He then surprised the worked-up crowd by bringing out country newcomer Tyler Reeve for a quick acoustic version of “In Case You Didn’t Know,” the song he co-penned with Brett Young alongside fellow writers Trent Tomlinson and Kyle Schlienger. The show went high tilt from there with “Raised on Country,” “I’m Comin’ Over,” “Voices” and a cover of the Keith Whitley classic “When You Say Nothing at All.” Young then threw out shoutouts to his parents ("they are somewhere here tonight"), to Cassadee Pope before “Think of You” and to Vince Gill before “Sober Saturday Night.”

But perhaps the most touching part of the night was when the cell phone lights went on for Young’s subdued performance of the ultimate tearjerker of 2019, “Drowning.”

“How the hell do we get out of that?” he said at the conclusion of the somber song, wiping what looked like sweat — but could have been tears — out of his eyes.

But in true headliner fashion, he found a way to put the crowd back into a frenzy with the Garth Brooks cover “Papa Loved Mama,” before finishing the night off with his own hits such as “Tomorrow,” “The Man I Want to Be” and “Aw Naw.”

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