Olivia Rodrigo and Yungblud Join Smashing Pumpkins at Lollapalooza 2025

Smashing Pumpkins headlined Lollapalooza on July 31 for the first time in 32 years, and Billy Corgan made sure Chicago felt the weight of that moment. He brought out Olivia Rodrigo and Yungblud as surprise guests, each singing a deep cut from the band's nineties catalog in front of a festival crowd that had no idea what was coming.

Yungblud hit the stage first, less than an hour after wrapping his own Lollapalooza set, to sing "Luna" from 1993's Siamese Dream. He handled the song's falsetto while Corgan played guitar behind him. The moment clearly meant something to the British rocker. He told the crowd it was a dream come true.

Rodrigo followed, introduced simply as "a very, very special guest." She sang "Thirty-Three" from Mellon Collie and the Infinite Sadness, Corgan switching to acoustic guitar as the stage went red. The pairing made sense on paper and landed even harder in practice. Rodrigo has been open about how nineties alt-rock shaped her as a writer, and her catalog backs that up. SOUR and GUTS both debuted at No. 1 on the Billboard 200, and she has three Hot 100 chart-toppers to her name.

Why the Smashing Pumpkins and Olivia Rodrigo Collab Moment Matters

This was not a random booking. Corgan spent the entire week building toward this set under the banner of "Pumpkinpalooza," which included a sold-out show at the Riviera Theatre, a merch pop-up near Grant Park, and a roving version of his own teahouse. The Lollapalooza headline slot was the culmination of a carefully staged hometown celebration.

The Mellon Collie legacy is worth keeping in context. The album debuted at No. 1 on the Billboard 200 in 1995, is the only Pumpkins record to top that chart, and has since been certified diamond by the RIAA. "Bullet With Butterfly Wings" won a Grammy. The album earned seven nominations total. Yungblud is operating from a similar place of earned credibility right now: he won his first Grammy earlier this year for Best Rock Performance, for his performance at Ozzy Osbourne's farewell concert.

Both guest appearances carry a through-line. These are artists who absorbed the Pumpkins' influence, built their own audiences on the back of it, and then stood on the same stage where that lineage began.

Corgan also brought out former touring bassist Melissa Auf der Maur at an aftershow earlier in the week, adding another layer of reunion energy to an already loaded run.

The band is not done. The Rats in the Cage tour launches September 30 in Columbus, Ohio, built around a set celebrating the 30th anniversary of Mellon Collie and the Infinite Sadness, with a career-spanning second act alongside it. If the Lollapalooza week was any indication, Corgan has a clear vision for how this anniversary cycle plays out, and he is not treating it as a victory lap.

For artists and creators watching: this is what catalog stewardship looks like at the highest level. Corgan tied a major anniversary to a living cultural moment, brought in artists who actually connect to that legacy, and turned a festival headlining slot into something people will talk about for years. Check [/events](/events) for any tour dates landing near LA as the Rats in the Cage run gets closer.