Olivia Rodrigo Brings Out Weezer For Two Songs At Lollapalooza

Great idea, right?

Olivia Rodrigo was joined by 3/4 of Weezer (sorry Pat) during her headlining appearance at Lollapalooza Friday (8/1) in a moment that had most of Grant Park singing ooh-wee-ooh.

It was a cross-generational moment that could be the co-headlining tour we never thought we needed.

Olivia is on fire right now as she continues her journey of headlining festivals and helping educate her young fans with music her parents, let's say, were into.

In just the last few years she has headlined the Governors Ball in New York, Glastonbury in England, Pinkpop in the Netherlands, British Summer Time Hyde Park in London, Roskilde Festival in Denmark, Rock Werchter in Belgium, NOS Alive in Portugal, Mad Cool in Madrid, I‑Days in Milan, Pa’l Norte in Mexico, Osheaga in Montreal, and Festival Estéreo Picnic in Bogotá.

The only glaring fest she hasn't headlined is Coachella who spotlighted Lana Del Rey, Tyler, the Creator, and Doja Cat in 2024; and Lady Gaga, Green Day, Post Malone in 2025.

Should she have replaced Doja last year? Of course. Instead she did a guest appearance with No Doubt which helped her fans see the rock-n-roll dotted line between Gwen and herself.

In Chicago on Friday she got to play "one of my favorite songs of all times" with Rivers Cuomo, Brian Bell and Scott Shriner.

Beaming while strumming along on her red Fender Jazzmaster, Rodrigo traded verses and also added some background vocals to "Buddy Holly," which Weezer broke through with in 1994.

If Weezer made it seem simple, it's because they've played the hit over 1,400 times in 30 years.

They then broke into "Say It Ain't So," which they've rocked live over 1,300 times.

You know the one. The slow jam that's "a water slide away from me
that takes you further every day -- so be cool."

How old are these songs compared to how young Olivia is? Our girl was negative 8 years old when these tunes were flying off the shelves of record stores along with "The Sweater Song" on Weezer's eponymous debut, affectionately called The Blue Album.

Weezer created that first record, Rivers paused to enroll Harvard, they then made a second perfect record, Pinkerton, and then put out two more records before Olivia was even born.

Since Olivia was born, Rivers and his funky bunch have released 11 studio albums and 6 EPs.

Here are the LPs alone: Make Believe (2005), Red Album (2008), Raditude (2009), Hurley (2010), Everything Will Be Alright in the End (2014), White Album (2016), Pacific Daydream (2017), Teal Album (2019), Black Album (2019), OK Human (2021), and Van Weezer (2021).

None of this is news for Olivia who before she brought out the veteran group (minus their drummer) she said, "I remember my first concert… that incredible band is actually here tonight.”

Now this is where you might cry, "say it ain't so."

That's it for Olivia, tour-wise. She did over 100 shows for Guts and now with this gig in Chicago that's the last dance on her dancecard.

Should she go on a mini tour with her first concert BFFs, Weezer? Yes. Of course. Definitely. Should Coachella offer her a Friday headlining spot for next Spring's fest? Yes, of course. Definitely. But who knows what schedules are going to shake out.

Maybe she takes the rest of the summer off and soak in the loveliness of being 22 like Taylor sang, and dressing up as a hipster. Or maybe she rushes back in the studio, makes some magic and is ready next spring to do that overdue Coachella with new tracks. She's easily one of the hottest stars on the circuit who seems to be enjoying every step.

She's come a long way from being sad over a boy after getting her drivers license.





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Last updated: 14 Aug 2026, 14:06 UTC

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