Olivia Rodrigo walked onstage during The Smashing Pumpkins' headlining set at Lollapalooza in Chicago on Friday, 31 July, to sing 'Thirty-Three', a track from the band's 1995 double album Mellon Collie and the Infinite Sadness (Pitchfork, 2 August).

She was not the only guest. YUNGBLUD opened the set by joining frontman Billy Corgan for 'Luna', and former Pumpkins guitarist Melissa Auf der Maur — best known as the bassist in Hole who also spent a stretch in The Smashing Pumpkins — came out for 'The Everlasting Gaze', from 2000's Machina/The Machines of God (Pitchfork, 2 August; Rolling Stone, 31 July).

Each guest performed one song with the band, according to USA Today, 1 August. The Smashing Pumpkins' official Instagram account described Rodrigo's appearance as a surprise acoustic performance, and the official Lollapalooza Facebook page posted video of the moment.

For Rodrigo, who released her second album Guts in 2023 and has spoken openly about her admiration for 1990s alternative rock, singing a Pumpkins deep cut in front of a festival crowd places her squarely in a lineage she has cited as an influence. Mellon Collie and the Infinite Sadness topped the Billboard 200 on its release and remains the band's most commercially successful record. 'Thirty-Three', originally a single from that album, gave Rodrigo a chance to trade vocals with Corgan on a song written before she was born.

Auf der Maur's return carried its own history. She joined Hole in 1994 following the death of Kristen Pfaff, then moved to The Smashing Pumpkins in 1999 for the Machina sessions and touring cycle. Her appearance on 'The Everlasting Gaze' reunited her with material from that period.

YUNGBLUD's contribution came early in the set. The Doncaster-born musician, whose work draws on punk and Britpop references, sang 'Luna' alongside Corgan — a track from the band's 1994 B-sides collection Pisces Iscariot that has rarely surfaced in recent live sets.

The Smashing Pumpkins' Instagram also teased something connected to the Lollapalooza performance arriving on 14 August, though no further details were given. The band has been touring through 2026 on a schedule that has mixed festival headlining dates with arena shows.

For the Lollapalooza crowd, the surprise guest spots compressed three decades of alternative rock into one headlining set — a Nineties icon, a former bandmate, a British newcomer and a pop star who grew up on the records, all sharing the same stage on a Friday night in Grant Park.