Five years after a spontaneous duet helped introduce Hailey James to millions of country music fans, the Cottage Grove native found herself standing beside Dustin Lynch again Friday night, singing the same song that changed the direction of her young career.
Lynch invited James onto the stage July 24 during his concert at Treasure Island Resort & Casino in Welch. Together, they performed “Thinking ‘Bout You” before the crowd inside the Island Event Center, recreating a moment that began unexpectedly at a Wisconsin country music festival in 2021. Afterward, James shared video of the performance online, describing it as a full-circle moment and thanking Lynch, his team and Treasure Island for helping make it happen.
The first performance happened when James was 17 and attending Country Fest in Cadott, Wisconsin, with her family. Her parents regularly attended the festival and had seats near the front. James went along that year without any expectation of becoming part of the show.
During Lynch’s set, he asked whether someone in the crowd wanted to join him for “Thinking ‘Bout You.” People seated near James knew she could sing and began pointing in her direction. James was not initially paying attention and had not heard Lynch’s invitation. Suddenly, she heard him asking whether she wanted to sing with him.
She accepted, climbed onto the stage and performed the duet without preparation. James remembered the words, worked the stage alongside Lynch and carried herself with enough confidence that the performance appeared far less spontaneous than it actually was.
Family and friends recorded the duet, and James posted their footage on Facebook. As interest grew, she created a TikTok account and shared the performance there the following month. Two versions of the video eventually collected more than six million views, and Lynch also shared the performance through his social media account.
The video continued to resurface during the years that followed, introducing new viewers to James and prompting repeated calls for the two singers to perform together again. On an earlier social media post, one follower wrote, “I would love to see a reunion of you two singing next time Dustin is in the area.”
James wanted the same thing.
“I think this was the reunion that not only I really, really wanted, but I think a lot of my fans, people who follow me, the people who have seen the video, I feel like it was a moment that we all just really wanted to make happen,” James said. “After five years, all the cards just played out in our favor.”
Even on Friday, however, James did not know whether the performance would happen. Shortly before the concert, Treasure Island informed her that she would be able to attend Lynch’s pre-show meet and greet.
James greeted Lynch and quickly discovered that the original performance had remained memorable for him as well. Video from the Treasure Island concert shows Lynch telling the audience that he remembered pulling James from the crowd five years earlier and that their performance was still circulating online.
“He was like, ‘I remember you and I’ve been seeing your stuff. I’ve been following you, and I really love to see it,’” James said. “He was just asking me how things are going in my music career.”
There was plenty to discuss.
Since the original duet, James has won five Midwest Country Music Association awards, including Female Vocalist and Songwriter of the Year in both 2022 and 2023. She has performed at U.S. Bank Stadium during Minnesota Vikings games and has opened for artists including Carrie Underwood, Dylan Scott and Terri Clark. Her growing list of appearances has taken her well beyond the smaller local stages where she began performing as a teenager.
Treasure Island has played a notable role in that growth. James first performed there as an opening act for Underwood in 2023. She returned to open for Clark in 2025, then came back Friday for the reunion that fans had been requesting.
“Treasure Island has been so great to me. My first performance there was opening for Carrie Underwood,” James said. “That just in and of itself showed me just how much Treasure Island has my back and has had my back from the start and wants to see me succeed.”
The reunion also arrived as James prepared for another step in her career. Her newest single, “Lemonade Stand,” is scheduled for release Friday, July 31. She plans to celebrate the release during the Wilkins Bone Lake Bash in Luck, Wisconsin, where her merchandise tent will include an actual lemonade stand.
It is another milestone for a performer who began singing at Country Nites Saloon in Hastings when she was 14. The venues have grown, the crowds have become larger and James now has awards, original music and major opening appearances on her resume.
Still, before Lynch invited her onto the Treasure Island stage, James took a moment to look around the room and appreciate where the unexpected journey had brought her.
“Right before he had called me up on stage, I took a moment to just kind of take a look at everything and realize, ‘This is my dream,’” James said.