Olivia Rodrigo Makes A New Guest-Filled Headlining Set

Olivia Rodrigo made her Lollapalooza debut one to remember. The pop star brought an unexpected twist to her headlining set on Friday night (Aug. 1).

Performing to a packed Grant Park crowd in Chicago, Rodrigo lit up the second night of the festival with a career-spanning set. What’s more, it was a moment of personal full-circle magic. As the crowd buzzed, she paused her performance to share a bit of her own musical origin story.

“You always remember your first concert. It’s a very, very special moment,” she told fans. “I remember mine so clearly. I watched this incredible band, and I’m completely over the moon because they’re actually here tonight to play a few songs.” That band? Weezer.

Hence, what followed was a moment of pure alt-pop synergy. Rivers Cuomo and crew joined Rodrigo on stage to perform two of their most beloved tracks. So, fans enjoyed spiky power-pop anthem “Buddy Holly” and the anthemic “Say It Ain’t So.” Olivia Rodrigo traded vocals with Cuomo and shredded on guitar. In this manner, she showed love for the band that helped shape her early musical taste.

Olivia Rodrigo Brings Generations Together

The crossover collaboration marked Weezer’s first appearance at Lollapalooza in two decades. Their last performance was a co-headlining slot with Widespread Panic back in 2005.

Rodrigo, who’s carved a reputation for pulling legendary surprise guests at festivals. So, she proved once again she’s not afraid to bridge generations and genres. Her curatorial instincts make each guest feel like a heartfelt tribute rather than a gimmick.

Her Lollapalooza set also showcased her evolution as a performer. Opening with high-octane cuts like “obsessed” and “Ballad of a Homeschooled Girl.” Olivia Rodrigo leaned into her punk-pop side before delivering fan-favorite ballads like “Driver’s License,” “Traitor,” and “Love Is Embarrassing.”

So, the four-day festival continued through the weekend, with RÜFÜS DU SOL and TWICE headlining Saturday, and Sabrina Carpenter and A$AP Rocky closing out Sunday. Yet, if there was one moment that set the bar for surprise and sentimentality at Lolla 2025, it was Rodrigo and Weezer. The two generations collided in the best way possible.