Lollapalooza 2025 Was Loud, Packed, and Unapologetically Unhinged

Lollapalooza 2025 delivered the kind of sharp, unpredictable moments that continue to define the festival decades after its launch. What started in the early ‘90s as a farewell tour for grunge band Jane’s Addiction has long outgrown its alt-rock roots, transforming into a four-day cultural barometer that now sits alongside Coachella, Glastonbury, and Primavera as one of the music world’s most closely watched weekends. This year’s edition doubled down on generational transitions: welcoming a new wave of headliners who brought global momentum, while still giving space to local stories and fringe sounds at the forefront. 

Chicago’s Grant Park pulsed with a balance of chaos and clarity: sets that spiraled into cathartic sing-alongs, quiet arrivals that turned into breakout performances, and artists who used the stage not just to entertain, but to leave their mark in today’s pop music pantheon. Each day had its highlights, and any time could be a moment that the crowd was bearing witness to an artist who could end up shaping the next five years of music. 

Below are five of the most unpredictable moments from Lollapalooza 2025. 

Olivia Rodrigo’s Nerd Pop Arc

Pop-rock artist Olivia Rodrigo made one of the weekend’s most unexpected choices by inviting nerd pop band Weezer onstage for a live version of “Buddy Holly.” Rodrigo has made no secret of her respect for ‘90s alt-rock and grunge, and having Rivers Cuomo share the spotlight sent a clear message. Already making waves by bringing The Breeders along as openers and performing with Robert Smith in earlier tour stops, this Lollapalooza appearance suggested she’s ready to embrace the heavier edges of her songwriting even more publicly. 

 Sabrina Carpenter Arresting TWICE

Pop singer-songwriter Sabrina Carpenter, on the other hand, leaned into theater. At one point during her set, she walked onstage and ultimately sighted the three members of TWICE — Sana, Jihyo, and Momo — all mock-“arrested” in pink fluffy handcuffs. This bit built on the performance of “Juno,” whereas Carpenter found a lane that leaned into absurdity without losing the musical core. 

Give Chance The Rapper A Second Chance

Chicago-born hip-hop artist Chance the Rapper made his presence felt with a surprise set that had people rushing to Perry’s stage as soon as word got out. Though he’s stayed relatively quiet since the release of The Big Day in 2019, his brief 15-minute performance tapped back into the voice that once defined Chicago’s indie rap momentum. He powered through “No Problem,” “All Night,” and “Cocoa Butter Kisses” like he never left, before switching gears into new material. The back half of his set teased songs from Star Line, his upcoming album slated for release in two weeks. 

The School of Doechii

Doechii brought the concept and execution together better than almost anyone else on the lineup. Her set looked and moved like a stage production, complete with desks, choreographed transitions, and the full setup of a themed performance, running the show from start to finish. Surrounded by dancers dressed as classmates, she pushed through high-energy versions of “Yucky Blucky Fruitcake” and “Swamp Bitch” with total control. Doechii later used the final minute of her set to announce a headlining tour, closing the set with an economy that shows she’s not just thinking about festival moments but long-term moves for her ongoing world tour.

TWICE’s  Mic Cut Off

The festival closed with a historic moment for K-pop fans as TWICE became the first girl group from South Korea to headline Lollapalooza. Their 16-song set included hits like “Fancy,” “I Can’t Stop Me,” “What is Love?” and “Feel Special,” with each performance met by a sea of lightsticks and fan chants that nearly drowned out the music itself. There was also a moment where a KPop Demon Hunters reference, where the drones spelled out “The Honmoon is Sealed” with the fans reacting wildly to the drones up in the sky. But the final moment was as chaotic as it was telling. As the crowd chanted for an encore, the group returned to wave and try to engage, only to find their mics suddenly cut off. Whether it was a technical issue or a hard stop from the festival organizers wasn’t clear, but the crowd made its disappointment obvious. However, the group held formation and bowed out, showing that they had nothing to prove. The milestone had already been made.