Olivia Rodrigo made a surprise appearance during The Smashing Pumpkins’ Lollapalooza performance in Chicago, joining the band for “Thirty-Three.”
The collaboration took place July 31 during The Smashing Pumpkins’ festival set. Rodrigo shared the stage with the Chicago alternative-rock veterans for the song from their landmark 1995 double album, Mellon Collie and the Infinite Sadness.
The pairing connected two generations of alternative music. Rodrigo has frequently drawn from guitar-driven pop and rock traditions, while The Smashing Pumpkins helped define the sound and scale of 1990s alternative rock.
“Thirty-Three” stands apart from many of the band’s heavier songs. Its gentler arrangement and reflective tone gave the collaboration room to focus on the vocal exchange and the unexpected nature of Rodrigo’s appearance.
Several surprise guests join the Chicago set
The Smashing Pumpkins also used the Lollapalooza set to bring out additional guests. Melissa Auf der Maur appeared for “The Everlasting Gaze,” while Yungblud joined the band for “Luna.”
Rodrigo’s appearance became one of the festival’s most widely discussed crossover moments, combining a current pop headliner with a band deeply tied to Chicago’s rock history.
The performance arrived during a busy period for Rodrigo, whose live appearances have continued to emphasize her connection to older rock and alternative influences. For The Smashing Pumpkins, the guest spot added a fresh voice to a song that has remained a fan favorite for three decades.
A fan-shot document of the Lollapalooza collaboration circulated after the set. For a stable official embed, 45Audio is using The Smashing Pumpkins’ official video for “Thirty-Three.”
