Olivia Rodrigo Rocks Out With Weezer During Headlining Lollapalooza Set

August 3, 2025 – Radio 854 Music News

Chicago’s Grant Park lit up Friday night as Olivia Rodrigo delivered a magnetic headlining debut at Lollapalooza 2025, bringing her signature mix of raw emotion, rock energy, and star-studded surprises. As part of her GUTS World Tour, Rodrigo electrified the packed crowd with hits spanning both her breakthrough album Sour and her follow-up Guts.

oward the end of her set, Rodrigo pulled off one of the most memorable moments of the weekend by inviting rock icons Weezer onstage. Fans erupted as they watched her perform two classic tracks—“Buddy Holly” and “Say It Ain’t So”—joining frontman Rivers Cuomo in a nostalgic, high-octane performance.

The moment was deeply personal for Rodrigo: she revealed to the audience that Weezer headlined the first concert she ever attended. “You always remember your first concert… that incredible band is actually here tonight to play a few songs,” she said, visibly emotional and overjoyed.

Rock Meets Pop-Punk: A Full-Circle Moment

This collaboration marksw a beautiful full-circle moment in Rodrigo’s artistry. Having invited luminaries like David Byrne (Talking Heads) at Governors Ball and Robert Smith (The Cure) at Glastonbury earlier this festival season, Rodrigo continues her streak of inviting heroes to join her onstage in unexpected and electrifying ways.

This time, fans weren’t just witnessing pop excellence—they were watching an emotional rock homage unfold live across Grant Park.

Rodrigo’s set was a masterclass in musical storytelling—from intimate ballads like Drivers License and Jealousy, Jealousy to crowd-favorite bangers Vampire, Traitor, and Bad Idea, Right?

With tens of thousands singing every lyric back to her, Rodrigo proved again why she’s one of Gen Z’s defining singer-songwriters. She encouraged audience participation throughout, transforming the crowd into a chorus that echoed her blend of confessional poetry and cathartic release.

✨ What It Means

For Rodrigo, performing at Lollapalooza marked a major milestone in 2025. She joined a festival lineup that included Korn, TWICE, Sabrina Carpenter, A$AP Rocky, and more across four genre-spanning days.

Her guest collaborations underscore her evolving identity—not just as a pop sensation, but as a curator of rock’s emotional past and today’s teenage angst. And with another festival appearance looming at Montreal’s Osheaga later this summer, fans are buzzing: could Arcade Fire be next?

In Summary

Olivia Rodrigo’s headline set at Lollapalooza 2025 was nothing short of iconic. With hits from Sour and Guts, a stunning live presence, and a surprise guest slot with Weezer that brought everything home, Rodrigo showed why she’s a force generating crossover energy between pop and rock. It was a performance that felt personal, powerful—and utterly unforgettable.