The party of the summer began Thursday as Lollapalooza kicked off its first day in Chicago's Grant Park, with the shadow (or cloud) of looming storms lingering overhead all day long.
Despite the threat of severe weather, rain held off for most of the day, as numerous fans decked out in their finest pink cowboy hats, glitter, mesh wear and makeshift Chappell Roan-like outfits filed into the park, eagerly awaiting the fast-rising star's performance later in the day.
From the beginning, it was clearly a day ruled by strong performances from women. Over on the Tito's Handmade Vodka stage, singer Abby Holliday opened the stage as one of the festival's first time slots, with an intoxicating set capped by infectious single "Better By Now," which turned into an all-out singalong by the final minutes.
Over at the T-Mobile stage, Variance favorite METTE was the opening act, but her delivery was that of a seasoned performer, capturing the crowd with her big, pop performances from her grand entrance, flanked by a trio of male dancers. We loved every second of her performance, as she proved she's certainly ready for the big leagues.
Tyla's performance later on the same stage was another instant highlight, as she has seen her star rise. Fans were clamoring to get to the stage, especially leading up to her big finale of her massive single "Water," which echoed throughout Grant Park as she closed out her set.
Similarly, British singer Olivia Dean was also a bright spot in a busy lineup, as she delivered soulful, velvet live renditions of her songs for a sea of fans around the IHG Hotels & Resorts stage.
Of course, perhaps the biggest performance of the day wasn't enough a headliner, in the case of Chappell Roan, who was wisely moved several weeks ago from the IHG stage to the T-Mobile stage, as festival organizers clearly learned from past experience with acts such as Lizzo and Billie Eilish, both of whom performed on smaller stages as they were breaking out into the mainstream.
As we mentioned, the fans in attendance on Thursday were definitely there for Roan, as a flood of pink covered the grounds all day. So, it was no surprise as the field in front of the T-Mobile stage quickly filled up, with tens of thousands of on-lookers filing in to get a glimpse of the singer, who has recently been on tour, playing smaller venues which were booked long before she suddenly broke out.
The queer singer entered fully in character, with a large wrestling ring on stage behind her while wearing a custom, latex wrestling outfit designed by Busted Brand (who designed Beyoncé's Cowboy Carter album cover outfit) and a custom leather wrester's mask designed by Zana Bayne.
If the festival later confirms there were 100,000 on hand for Roan's performance, we wouldn't be shocked. The crowd was that unreal, going as far as the eye could see. Don't be surprised if she's back in 2026, this time as an actual, proper headliner.
To be clear, sometimes timing can be tricky, especially as many of these large, mainstream festivals book out their lineups months and even a year in advance. But it's not unheard of for Lolla to miss it, as was the case with one of Thursday's actual headliners, Megan Thee Stallion, who last performed in 2021, drawing an enormous crowd and delivering an intense performance. At the time, we declared, she "was our headliner, and you can't tell us otherwise."
Yet, when this year's lineup was initially announced, Tyler, the Creator was one of the headliners until he suddenly backed out, prompting organizers to book Megan in his place. It was an easy swap, as Megan has maintained her stardom, and coincidentally made a buzzworthy guest appearance at Kamala Harris's massive rally in Atlanta earlier this week. Harris herself has quickly risen to the top of headlines as she has replaced Joe Biden at the top of the Democratic party's presidential ticket in a political year unlike any other.
For Megan's own return to Lollapalooza, yes, it does seem slightly late to be receiving her flowers as an official headliner, when she very well could have had that role in prior years. But it was nice to see her thrive in this moment. Perhaps, she also recognized the irony on her own, as she greeted the crowd on Thursday night, exclaiming, "Chicago!" to a roaring crowd, telling them, "We're here—again!"
Nonetheless, it was a big first day, and a giant spotlight was certainly shining on so many women performers, further proving women can be and should be headlining top-tier festivals. And maybe in a few short months, a woman could even be President.
