Smashing Pumpkins Feature Olivia Rodrigo and Yungblud at Lollapalooza

The Smashing Pumpkins turned their headline slot at Grant Park into an unexpected generational bridge on July 31, 2026. For their first Lollapalooza headlining appearance since 1994, band leader Billy Corgan bypassed pure nostalgia and instead drafted contemporary pop royalty into the lineup. The band brought out British alt-rocker Yungblud and pop star Olivia Rodrigo as surprise guests during a brisk 17-song performance on the festival’s Bud Light Stage.

Yungblud Joins Billy Corgan for Siamese Dream Deep Cut

Taking the stage less than an hour after finishing his own festival set, Yungblud stepped up alongside Corgan to deliver a soaring version of “Luna,” the closing track on the Smashing Pumpkins’ second studio album, 1993’s Siamese Dream. Both musicians wore matching all-black outfits as the British artist handled the song’s falsetto verses while Corgan backed him on guitar.

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“This is a fucking dream come true!”

Yungblud, via Rolling Stone

The collaboration underscored a mutual appreciation between the veteran alt-rock pioneers and newer artists threading the nineties alternative lineage. Yungblud earlier noted the profound influence of the four-time-platinum LP on his own musical upbringing, earning public praise from Corgan who remarked that his star shines bright after the two previously collaborated on a version of the song Zombie earlier in the year.

Olivia Rodrigo Steps In for Mellon Collie and the Infinite Sadness Classic

Following the first guest spot, Corgan introduced the festival’s next surprise addition. And now I’d like to bring out a very, very special guest. Miss Olivia Rodrigo! Rodrigo appeared on stage wearing a sheer baby doll dress and knee-high stockings as the stage washed in red light and a steady rain began to fall across Grant Park.

With Corgan switching to an acoustic guitar, Rodrigo delivered “Thirty-Three”, a single from the band’s 1995 double album Mellon Collie and the Infinite Sadness. That commercial high point debuted at No. 1 on the Billboard 200 with 246,500 first-week units and earned a diamond certification from the RIAA for sales exceeding 10 million copies.

The pairing fit neatly into Rodrigo’s touring history of inviting rock royalty onto her own stages, following previous surprise guest appearances with figures like Robert Smith of The Cure, Weezer, David Byrne, Avril Lavigne, and No Doubt. For the festival crowd braving the sporadic downpours, the collaboration offered a visceral link between nineties guitar rock and modern pop chart dominance.

Pumpkinpalooza and the Road Ahead

The high-profile guest spots capped an intense week of hometown celebrations dubbed “Pumpkinpalooza”. The festivities included a sold-out underplay show at the 2,500-capacity Riviera Theatre, an exclusive merchandise pop-up on Wabash Avenue, and a festival-exclusive activation of Madame Zuzu’s Celestial Lounge offering matcha and vinyl on the festival grounds. During the pre-festival aftershow, the band welcomed actor Barry Williams—Greg Brady from The Brady Bunch—to perform the Seventies sitcom tune It’s a Sunshine Day.

The Lollapalooza set also featured a reunion with former touring bassist Melissa Auf der Maur, who joined the band to play “The Everlasting Gaze” from 2000’s Machina/The Machines of God, mirroring a guest appearance she made earlier in the week at their intimate club show.

Following their triumphant return to Grant Park, the Smashing Pumpkins turn their attention toward their upcoming Rats in the Cage tour.