In a moment straight out of a movie, a woman unknowingly sang “Heart Like a Truck” right to Lainey Wilson—without realizing who she was. On a lively Nashville street, Lainey went undercover in her signature bell bottoms with Are You Kidding TV, looking for someone to sing one of her songs for $500. The catch? No one knew it was her. People passed by, laughed, and gave it a try—but then came one woman, rocking bell bottoms of her own. Nervous but game, she sang her heart out. When Lainey finally stepped forward and said, “I’m Lainey Wilson,” the woman froze, gasped, and blurted, “Oh sh*t. Are you kidding me?” One song, one street, one perfect surprise.

Although focused on becoming one of the top females in country music, Lainey Wilson doesn’t mind having a little fun. Recently, the singer found herself standing in downtown Nashville, waiting for the right person to sing one of her songs. Joining forces with Joe and Steven for Are You Kidding TV, the three offered bystanders a chance to win $500. While some might see the challenge as easy, one lucky fan had no idea she was singing “Heart Like A Truck” to the person who helped write the song.

Standing between both Joe and Steven, Wilson remained silent as bystanders quickly learned that one of them would win $500 if they could sing a single song from the singer. But there was a catch. Given the stardom surrounding Wilson, the country star was known for wearing bell bottoms. In the video, she donned the signature look. With people passing by, one person noticed the sign with the rules, but sadly, she wasn’t wearing bell bottoms. Eventually, the crowd found a person wearing bell bottoms and encouraged her to sing a song.

While admitting she was a little embarrassed, the woman took on the challenge, performing a snippet of Wilson’s “Heart Like A Truck.” It was only after she finished that Wilson introduced herself, causing the woman to lose her composure. “Oh sh*t. Are you kidding me?”

Lainey Wilson Explains Her Love For Bell Bottoms

Besides winning $500, the woman also received a chance to share a drink with Wilson. While at the bar, the singer announced she would match the $500 and give it to a charity of her choice.

Online, fans discussed how they would have handled the situation with one person wanting more than the money. “I would have skipped the 500 dollars, taken selfies, hugged her, convinced her we were best friends and had drinks at her bar with her. I would have been wearing her cowboy hat though. Love you Lainey!”

Given Wilson’s love for bell bottoms, she once admitted she decided to wear the clothing as a way to stand out. “I was really trying to figure out what could I do to stand apart from the rest of the females in Nashville, because it’s very important to do that. And what is something that is really true to me? And for me it was whole bell bottom throwback look.”

Embracing classic clothing, Wilson proved time and time again that her talents went far beyond her fashion sense with hits like “4X4XU” and “Watermelon Moonshine.”