RESOLVING THE LEDGER
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Each night of Lollapalooza offers four competing headliners, and oftentimes it's difficult to choose where to land at the end of the night. The second night of the 2026 edition in Chicago's Grant Park was no exception, with the evening offering Charli XCX , the Smashing Pumpkins , Major Lazer, and Freddie Gibbs as its top line. If there was a night this year for headlining FOMO, it was this one. And even the rain that steadily fell through the day and evening couldn't dampen that feeling.
The two main stage spots belonged to Charli, whose return to Lolla also marked her first festival date following the release of her excellent Music, Fashion, Film , and the Pumpkins, the hometown heroes who made their official Lollapalooza Chicago debut (they previously performed the OG traveling Lolla version back in 1994). Both rocked their respective sides of the park.
For their set, Smashing Pumpkins leaned into material from Mellon Collie and the Infinite Sadness , their third studio album that turned 30 last October, alongside classics from Siamese Dream as well as songs from recent album Aghori Mhori Mei , including "Edin."
They also surprised fans with a couple of guests early on, including Yungblud , who sang "Luna" from Siamese Dream . Yungblud, who performed earlier in the night, remarked the moment was "a dream come true." A few songs later, Olivia Rodrigo joined frontman Billy Corgan for an elegant, acoustic performance of "Thirty-Three." Their appearances highlighted Smashing Pumpkins' resonance over more than three decades, and their influence on the next generation of rock stars.
Meanwhile on the other side of Grant Park, Charli XCX was holding court on the T-Mobile stage with her apt backing band and a bevy of dancers. Though she's played a couple intimate one-off shows ahead of her appearance on Friday, Charli XCX officially kicked off her tour behind Music, Fashion, Film in Chicago at Lollapalooza. It was a grand return for the star, who has taken the stage at Lolla in Chicago in previous years, including in 2015, 2017, and 2022 — each performance a showcase of her evolution. She kicked off her new era at the fest with "Rock Music." Editor’s picks The 250 Greatest Albums of the 21st Century So Far The 100 Best TV Episodes of All Time The 500 Greatest Albums of All Time 100 Best Movies of the 21st Century
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