It rained underwear at Grant Park as Charli XCX tore into her raunchy hit 'Guess' during her Lollapalooza 2026 headline slot. The crowd responded by throwing handfuls of underwear towards the stage, creating a chaotic and unfiltered recreation of the song's famous music video. Yet barely 20 minutes later, that same crowd watched as the cheerful spectacle of neon and flying knickers transformed into a genuine downpour. With fire and an intense monologue from John Cale, Charli seemed to be signalling the end of the Brat era.
Was this a calculated rebrand from a pop star bold enough to walk away from her most lucrative aesthetic at its absolute peak, or a self-indulgent pivot that risks alienating the very fans who spent 2024 chanting her name in lime green? Charli left Grant Park with no viral 'Apple' dance, no celebrity cameos and not a scrap of green in sight.
Was Charli XCX's Lollapalooza Rain Moment Staged or Coincidental?
Nobody controls the Chicago sky, but the timing bordered on theatrical. As John Cale's voice rang out to introduce 'House', her brooding cut from the Wuthering Heights soundtrack, the downpour intensified on cue. Charli reappeared through pyrotechnics to finish the track rolling in puddles, turning a weather delay into an accidental rock-opera climax.
Performing 'Guess' amid a blizzard of underwear wasn't a new party trick, considering she pulled a similar panty-dropping stunt live at the 2025 Grammys. But where her television moment was carefully orchestrated, the Lollapalooza moment was something far less controlled.
Standing drenched in genuine Chicago rain, backed by pyrotechnics and a Velvet Underground legend, Charli proved she no longer needs staged gimmicks or a sunlit platform to dominate a festival.
@entertainment_weekly You don't have to guess the color of these underwear! #CharliXCX may not have brought out BillieEilish, but she did make it rain lingerie during her performance of "Guess" at her headlining #Lollapalooza set.
♬ original sound - Entertainment Weekly
Is 'Brat' Summer Officially Over?
The absence of green was noticeable. There were no lime lights, no Brat branding, and nothing to connect the show to the aesthetic that had defined pop culture for two consecutive years. Instead, Charli opened with 'Rock Music' from her new album Music, Fashion, Film, allowing heavier guitars and drums to set the tone for the night.
Purists in the crowd, who had come ready to relive 2024, caught glimpses of it through performances of 'Apple', '360', and 'Von Dutch'. Yet these fan favourites served merely as supporting acts to a much darker main event.
In fact, her only true Brat triumph of the weekend happened a night earlier on someone else's stage, joining Lorde for 'Girl, so confusing'. It was a reminder that while Charli still respects her pop past, Friday night was strictly reserved for her future.
@lollapalooza Girl, so confusing 🔥 @Lorde @Charli XCX #lollapalooza #lorde #charlixcx
♬ original sound - Lollapalooza
Cashing in Her Pop Capital for Raw Rock
Landing her second UK number one album in a single calendar year gave Charli XCX the ultimate safety net, but she didn't use it to double down on the neon formula.
She had already signalled the move weeks earlier at Sundance, telling audiences while promoting her mockumentary The Moment that she was 'really wanting Brat to stop and actually really pivot as far away from it as possible,' adding that the urge came not from dissatisfaction but because, as she put it, artists need to challenge themselves.
@laurenashleybeck Charli XCX says she’s ready to pivot from brat at Subdance #charlixcx #brat
♬ original sound - Lauren Ashley Beck
Headline sets are usually designed to give the masses a predictable victory lap, and this one was a deliberate execution. By stripping away the lime green and walking away from her most lucrative aesthetic at its peak, Charli used 100,000 people as witnesses to prove her own point: Brat was a stop on the map, not a permanent home, and she isn't afraid to move on.
