CHICAGO — For singer-songwriter Tucker Pillsbury, who performs as Role Model, playing Lollapalooza isn’t new. His performance Thursday marked his third appearance at the festival, with the first two taking place in 2022 and 2019 when he was known for his alternative bedroom pop music.

“Twenty-nineteen was great,” the 28-year-old artist said in an interview with the Tribune. “I was still very nervous, little skinny boy wearing a leather vest with no shirt underneath, but it was fun. That was like a big moment, and I fell in love with Lollapalooza in 2019 and it’s still probably my favorite festival.”

Role Model’s fashion style and musical style have evolved since then. The Maine artist’s sound is now a mix of folk and indie pop, with catchy, relatable lyrics that have gone viral on social media. His most recent album, “Kansas Anymore,” just celebrated its one-year anniversary, while its deluxe version, “Kansas Anymore (The Longest Goodbye),” earned Role Model his first Billboard chart appearance with the single “Sally, When the Wine Runs Out.”

Thursday’s performance offered a slight change in pace for the musician, who began a worldwide tour for “Kansas Anymore” in Europe in November 2024. Lollapalooza is early in a stretch of festivals he will play, including Hinterland in Iowa and Austin City Limits in Texas.

“On tour, you get to warm up and make sure things are working. With festivals, you just kind of go for it and hope it works out. But it’s fun,” Role Model said. “I like festivals because they feel like summer camp with you and all the artists. It feels like a little summer camp with people you look up to and peers and everything.”

Role Model has seen a lot of his peers lately. The artist was recently on tour opening for friend and singer-songwriter Gracie Abrams, who performed across the festival grounds at the T-Mobile stage 15 minutes after Role Model’s set ended at the Tito’s stage, a coincidence he poked fun at.

“That sucks,” Role Model joked about the timing. “I mean, I’m gonna be performing ‘Sally’ and it’s gonna be an empty crowd at the end.”

The single, released in February along with the rest of the deluxe album, quickly earned Role Model popularity on social media and the charts. It rose in prominence when the artist started bringing fans or surprise special guests on stage to dance during the song’s bridge, which describes a girl named Sally who can be a “diva” who Role Model beckons on stage when he shouts out “where’s my Sally tonight?” With famous figures like singer Reneé Rapp and actor Natalie Portman appearing as Sally, the song keeps the crowd guessing about who will appear onstage.

A year after the album’s initial release, Role Model said he is grateful people still care about him and his music.

“Especially now with attention spans going down, down, down, the dream is to have an album that continues to grow and doesn’t disappear after a couple weeks,” Role Model said. “That was a massive surprise to me, because all I think about is people’s attention spans and how long they’re going care about something and so for it to still be talked about and still be actively listened to is really cool.”

Six years after his first time performing at Lollapalooza, the artist said the festival is special because of the passionate attendees.

“I hope they just keep calling me back,” he said. “I mean it when I say Lollapalooza is my favorite festival here in the U.S. just because of the people and they care very much about music.”

Role Model’s latest Lollapalooza appearance showed how much people care about music, especially his. He performed to a crowd packed to the brim, with so many people trying to see him that it spilled into the area meant for the Bud Light stage.

The artist sang fan favorites from past albums between songs from “Kansas Anymore” in his hourlong set, stopping only to jokingly introduce his band as “The 1965” and “Imagine Dragons,” and to point security to someone who needed medical help.

Though the crowd was packed, there was still room for people to dance and sing. Role Model let the fans take the lead in songs multiple times, dancing while they sang his words back to him.

When it came time for “Sally,” it was clear the crowd would not be leaving as Role Model worried. The first chords of the song — like most of his songs played Thursday — elicited screams and cheers, amplified when the artist brought out singer the Dare to be his “Sally” and share a cigarette while dancing.

Though the crowd did file out following his last song, “Deeply Still In Love,” by then, Role Model had declared loudly that he was in love with Lollapalooza. Those left in the crowd indicated that they loved him too.

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