Olivia Dean Headlines Rain-Delayed Lollapalooza Day Three — SkimNews
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- Lollapalooza 2026 delayed Day Three doors by about three hours after overnight flooding left Grant Park pooled and muddy, with gates opening at 3 p.m. and some sets canceled or truncated due to the weather shift.
- Olivia Dean headlined the T-Mobile stage to a crowd stretching to the end of her side of Grant Park — a dramatic jump from a 2024 daytime set on a smaller stage and a 2025 Chicago headlining show that drew about 1,500 people; her banner year began with a Grammy for Best New Artist in February 2026.
- "Rein Me In" by Dean and Sam Fender spent 19 weeks atop the U.K. singles chart, surpassing Frankie Laine's 1953 record of 18 weeks at No. 1 held for more than 70 years; Dean brought Fender out as a surprise guest Saturday to perform the song live.
- Sienna Spiro, the 20-year-old rising star, packed the Airbnb stage with fans singing along to cuts from her debut album Visitor, including "Pure," "He's Not My Baby, I'm His," "Great Expectation," and closer "Die on This Hill."
- Dean and Spiro both evoked an "other-era quality" with orchestral arrangements and live horn sections, sounding "timeless and fresh" across the rain-soaked festival day.
Why it matters: Olivia Dean's Lollapalooza headliner follows a Grammy win in February and a record-breaking 19-week U.K. No. 1 with Sam Fender, while Sienna Spiro's packed Airbnb stage and debut-album reception mirror the same festival-climb Dean made from a 1,500-person Chicago show last year to today's T-Mobile headliner.
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