Charli xcx Headlines, Smashing Pumpkins Bring Out Olivia Rodrigo at Lollapalooza Day Two

Friday at Lollapalooza opened its second night with a headlining turn from Charli xcx, whose set leaned into the polished, high-energy pop that has marked her recent rise. It was a performance calibrated for the moment—sharp, self-assured, and visibly in command of a festival stage that has historically favored rock-leaning closers.

Earlier, Smashing Pumpkins turned their slot into a shared event, bringing out Olivia Rodrigo as a guest. The pairing bridged decades and audiences without feeling forced, adding an unscripted layer to a day that otherwise moved briskly through its lineup. Slayyyter’s hyperpop urgency, Yungblud’s theatrical rock, K-pop act I-DLE, and Suki Waterhouse’s hazy indie each carved out their own space, while Freddie Gibbs brought local weight and Finn Wolfhard’s Not For Radio—alongside masked duo Horsegiirl—filled the undercard with rougher edges.

With Olivia Dean, Jennie, The xx, and Turnstile still to come, the festival’s programming continued to test the boundaries between pop spectacle and left-of-center booking. On Friday, at least, that friction felt more deliberate than diffuse.