Smashing Pumpkins and Charli XCX Anchor a Rain-Soaked Lollapalooza Night

Lollapalooza’s second night in Chicago set up a familiar festival tension: four headliners, two main stages, and a crowd forced to choose. Smashing Pumpkins and Charli XCX each claimed a side of Grant Park on Friday, while steady rain made the decision feel heavier than usual. Major Lazer and Freddie Gibbs rounded out the top line elsewhere, but the evening’s pull came from the two opposing poles of guitar-driven legacy and tightly choreographed pop.

Smashing Pumpkins made their official Lollapalooza Chicago debut with a set that leaned into material from Mellon Collie and the Infinite Sadness, marking its 30th anniversary alongside songs from Siamese Dream and the recent Aghori Mhori Mei. Early guest spots underlined the band’s cross-generational reach: Yungblud stepped up for “Luna,” calling the moment “a dream come true” after his own earlier performance, and Olivia Rodrigo joined Billy Corgan for an acoustic, understated “Thirty-Three.” Neither appearance felt like stadium-level spectacle; both signaled a quieter transmission of influence.

Across the park, Charli XCX opened her tour behind Music, Fashion, Film with “Rock Music” and her apt backing band. The set moved through cuts like “SS26” and the B-side “If You Take Away the Music Then What Has She Got?,” tracing a line from her 2015, 2017, and 2022 festival appearances to this more deliberate, cinematic phase. The finale, “No One Lasts Forever,” nodded to David Cronenberg. Where the Smashing Pumpkins traded on nostalgia refracted through new guests, Charli’s return was all forward motion—a headliner no longer competing, just advancing.