Olivia Rodrigo returned to Lollapalooza Chicago in an unexpected way on Friday night (July 31), making a surprise appearance during The Smashing Pumpkins’ hometown headlining set at Grant Park. The pop superstar joined Billy Corgan onstage for a haunting performance of the band’s 1995 classic “Thirty-Three,” creating one of the festival’s most iconic moments.
The collaboration unfolded midway through The Smashing Pumpkins’ nostalgia-filled performance as light rain began falling over Chicago. Bathed in red lighting, Corgan accompanied the song on acoustic guitar while Olivia Rodrigo shared lead vocals, delivering a restrained yet emotional rendition that contrasted with the heavier moments elsewhere in the set.
The duet quickly became one of the defining highlights of Lollapalooza 2026. Fans packed in front of the Bud Light Stage erupted as Rodrigo walked out. The duo showcased strong chemistry, with Rodrigo’s expressive vocal delivery blending seamlessly with Corgan’s signature tone on one of the band’s most beloved deep cuts.
“Such a special moment for me singing my fav pumpkins song in the rain with the unparalleled @billycorgan !!!,” Olivia later wrote on Instagram. “feelin so lucky!!!”
The surprise didn’t end there. The Smashing Pumpkins also welcomed Yungblud for a performance of “Luna,” while former bassist Melissa Auf der Maur later returned to the stage for “The Everlasting Gaze.”
The moment served as another memorable chapter in Rodrigo’s history with Lollapalooza. She headlined several international editions of the festival throughout 2025 before closing the Chicago edition that August, where she surprised fans by inviting Weezer onstage for performances of “Buddy Holly” and “Say It Ain’t So.”
Olivia Rodrigo is currently celebrating the success of her third studio album, you seem pretty sad for a girl so in love, released on June 12 through Geffen Records. The project debuted at No. 1 on the Billboard 200 with the biggest opening week for a female artist in 2026, powered by hit singles including “Drop Dead,” “The Cure,” and “Stupid Song.” She is also preparing to launch her 86-date Unraveled Tour on September 25 in Hartford, Connecticut, beginning another major arena run across North America and Europe.
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