Smashing Pumpkins turned their Lollapalooza headline set into a generational summit on Thursday (July 31), with Billy Corgan bringing out Olivia Rodrigo and Yungblud as surprise guests for a pair of nineties deep cuts in Chicago.

The set marked the Chicago-bred band’s first Lollapalooza headlining slot in 32 years — they last played the festival in 1994, during its original touring incarnation, on a bill alongside the Beastie Boys, A Tribe Called Quest and Green Day. Corgan, a lifelong Chicagoan, had spent the week leading up to the performance staging a hometown celebration dubbed “Pumpkinpalooza,” including a sold-out underplay show at the 2,500-capacity Riviera Theatre, a merch pop-up near Grant Park, and a roving version of Madame Zuzu’s, the teahouse he owns with wife Chloé Mendel.

Yungblud arrived first onstage, taking his spot less than an hour after his own festival set to sing “Luna,” the closing track from the band’s 1993 breakthrough Siamese Dream. The British rocker, dressed in black to match Corgan, handled the song’s soaring falsetto as Corgan backed him on guitar. “This is a f—ing dream come true,” Yungblud told the crowd.

Rodrigo followed, introduced by Corgan as “a very, very special guest.” She appeared in a sheer dress and knee-high stockings to sing “Thirty-Three,” the fifth single from the band’s 1995 double album Mellon Collie and the Infinite Sadness, with Corgan switching to acoustic guitar as the stage was bathed in red light.

The pairings carried a certain lineage. Rodrigo has been open about the influence nineties alt-rock had on her sound, and both guests represent chart eras the Pumpkins helped make possible. Mellon Collie and the Infinite Sadness remains the band’s commercial high point — it debuted at No. 1 on the Billboard 200 in 1995 with 246,500 first-week units, the only Pumpkins album ever to top the chart, and was certified diamond by the RIAA for sales exceeding 10 million.

Its singles ran deep: “1979” became the band’s biggest Hot 100 hit at No. 12 and their only No. 1 on the Modern Rock Tracks chart, while “Bullet With Butterfly Wings” won the 1997 Grammy for Best Hard Rock Performance. The album earned seven Grammy nominations in all. Siamese Dream, the source of “Luna,” has been certified four-times platinum.

Rodrigo, for her part, arrived as one of the defining pop breakouts of the decade. Her 2021 debut SOUR and its 2023 follow-up GUTS both entered the Billboard 200 at No. 1, and she has scored multiple Hot 100 chart-toppers, including “Drivers License,” “Good 4 U” and “Vampire.” Yungblud has been threading the same alternative lineage: he won his first Grammy earlier this year, for Best Rock Performance, for his rendition of “Changes” at Ozzy Osbourne’s farewell Black Sabbath concert, and his Aerosmith collaboration EP One More Time reached the top 10 of the Billboard 200 in November.

The guest spots capped a week of nineties nostalgia. At a Lollapalooza aftershow earlier in the run, the Pumpkins brought out actor Barry Williams — Greg from The Brady Bunch — to perform the sitcom’s Seventies novelty hit “It’s a Sunshine Day,” and reunited with former touring bassist Melissa Auf der Maur for “The Everlasting Gaze,” from 2000’s Machina/The Machines of God.

The band now turns to its most ambitious outing in years: The Rats in the Cage tour, launching Sept. 30 in Columbus, Ohio, built around a set marking the 30th anniversary of Mellon Collie and the Infinite Sadness alongside a career-spanning second act.