The pop star rocked out with her childhood idols during a headline set fans won’t forget.
Olivia Brings The Nostalgia With Surprise Guests
Olivia Rodrigo lit up the second night of Lollapalooza 2025 with a surprise that sent fans into a frenzy. Making her headlining debut at Chicago’s Grant Park on Friday, August 1, the 22-year-old pop powerhouse stunned the crowd by bringing out none other than Weezer.
Toward the end of her set, Olivia paused to reflect on a personal memory. “You always remember your first concert. It’s a very, very special moment,” she told the crowd. “I remember mine — it was a very memorable night. I watched this incredible band… and that incredible band is actually here tonight.”
Moments later, Weezer took the stage to perform their 1994 alt-rock staples “Buddy Holly” and “Say It Ain’t So.” Olivia strapped on a guitar and harmonized with frontman Rivers Cuomo, blending generations of music in a moment that felt both nostalgic and electric.
A Summer Of Surprise Collabs
This isn’t the first time Olivia has stunned with a surprise guest. Earlier this summer, she brought out David Byrne at Governors Ball for a performance of Talking Heads’ “Burning Down The House,” and shared the Glastonbury stage with The Cure’s Robert Smith for “Friday I’m In Love” and “Just Like Heaven.”
Her Lollapalooza set followed that same magic. Kicking off with fan favorites like “Obsessed” and “Ballad Of A Homeschooled Girl,” she powered through hits including “Driver’s License,” “Traitor,” “Bad Idea, Right?” and “Love Is Embarrassing.”
Lolla Rolls On
Olivia’s genre-blending, guitar-shredding moment with Weezer was a clear highlight of the weekend — and one of her most personal performances to date.
Lollapalooza 2025 continues through the weekend with headliners Rüfüs Du Sol and TWICE on Saturday, and closers Sabrina Carpenter and A$AP Rocky wrapping things up Sunday night.
