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Lollapalooza Continues With Olivia Rodrigo, Weezer, T-Pain, Flipturn

COOK COUNTY, ILLINOIS, AUG 2 – Olivia Rodrigo honored her musical heroes by inviting Weezer to perform two songs during her nearly 90-minute Lollapalooza headlining set, showcasing her multi-instrumentalist talents.

  • On Friday , Olivia Rodrigo, 22-year-old pop superstar, invited rock band Weezer on stage during her Lollapalooza debut at Grant Park.
  • Sharing her backstory, Rodrigo told fans why Weezer mattered, revealing she saw them live first at her debut festival. This isn’t the first surprise guest.
  • Weezer joined Rodrigo to perform “Buddy Holly” and “Say It Ain’t So,” with Rivers Cuomo duetting on the classics.
  • Fans reacted enthusiastically, some calling it the most exciting moment of Lollapalooza so far, after NBC Chicago’s Matt Rodrigues posted video of the surprise.
  • Looking ahead, Weezer will headline Riot Fest in Chicago this September, as speculation grows over Rodrigo’s next surprise guest at Osheaga.
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Stereogum broke the news in on Saturday, August 2, 2025.
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