Olivia Rodrigo delivered a defining headlining performance at Lollapalooza Chicago 2025 on August 1. Taking the T-Mobile Stage at 8:45 p.m., the Grammy-winning singer held the crowd through a tight, emotionally charged 90-minute set that blended pop savvy, rock energy, and moments of pure vulnerability.
The night began with “obsessed,” setting a bold tone that barely let up. She carried that intensity through fan favorites like “drivers license,” “traitor,” and “vampire,” creating powerful emotional bookends around high-energy tracks like “brutal,” “all‑american b*tch,” and “good 4 u,” which closed the show on a triumphant note.
One of the most memorable moments came when Weezer unexpectedly joined Olivia on stage for iconic covers of “Buddy Holly” and “Say It Ain’t So.” The cross-generational mash-up thrilled fans and underscored Olivia’s ability to bridge present-day pop with legendary rock.
So far, Olivia has drawn one of the weekend’s most packed crowds, with fans lining up shoulder to shoulder across the front of the stage.
Related
Olivia Rodrigo’s Full Lollapalooza Setlist:
• obsessed
• ballad of a homeschooled girl
• vampire
• drivers license
• traitor
• bad idea right?
• love is embarrassing
• pretty isn’t pretty
• happier
• enough for you
• Buddy Holly (with Weezer)
• Say It Ain’t So (with Weezer)
• so american
• jealousy, jealousy
• lacy
• deja vu
• brutal
• all‑american b*tch
• good 4 u
• get him back!
Leave a Reply