At a pre-show on the Wednesday before Lollapalooza, bass player for The Regrettes Sage Nicole encouraged the audience to check out their set at the festival on Sunday.
"Oh yeah..." said frontwoman Lydia Night. "I forgot."
She smiled, giggled a little bit, and looked off into the crowd. In that moment, approaching the end of an acoustic performance in a small River North venue, it seemed to really hit the 17-year-old: Whoa, I'm about to play Lollapalooza.
"I don't know if you guys know, but this is my first Lollapalooza,” rapper Taylor Bennett, Chance the Rapper’s younger brother, announced to a crowd at Perry’s Stage on Friday. He pointed toward smokers on a hill to the left of the stage and reminisced about rolling up in that spot when he was only a kid from Chicago attending the festival as a fan.
Cuco, a 20-year-old Chicano singer from L.A., had a similar moment Thursday night, appreciating the gravity of what it means for a young artist to play their first Lollapalooza set.
"Yo, I never expected any of this," he said, uncontextualized, to an aftershow crowd in Wicker Park. That was around 1 a.m., after his exhaustingly long day that started with a 1 p.m. performance.
“This” was probably a combination of packing a mainstage, seeing die-hard fans at an intimate aftershow, and generally making it big as a first-generation kid; at both shows he gave shout-outs to youth immigrants and their working parents. Of course, the trippy lo-fi artist also shouted-out his “psychedelic heads,” of which there seemed to be no shortage in Chicago this weekend.
He cried onstage at the aftershow, overwhelmed by all the emotions. Before playing his song "Lucy," he said to the crowd, "Make me forget that I'm miserable by getting lit to this." Cuco has been sad lately—he’s been tweeting about it from his handle @Icryduringsex—but the energy of Lollapalooza seemed to help.
Throughout the festival, the rowdiness of the event contrasted with artists’ and fans’ inclination toward music that is open about loneliness and depression. On Friday, Tyler, The Creator got thousands of fans shouting repeatedly in unison, "I can't even lie, I've been lonely as fuck." Lewis Capaldi said he knew it was a hot day and that everyone was drinking and having a good time, but he asked the crowd "if we could just be sad for the next 30 minutes" for his set.
Lil Uzi Vert also seemed to be struggling. Drawing a huge crowd on Sunday to the mainstage, his performance was strong until the last 10 minutes, at which point he threw his mic into the audience, saying he wanted to hear us sing, and promptly left the stage. The crowd was unsure of what was going on—Was his set over? Was he coming back?—when “XO TOUR Llif3,” a song he had just performed, quickly began playing again. Vert’s hype man remained onstage alone, unclear what to do without the man he was supposed to hype.
Then there were artists in the midst of explosive mainstream popularity. Despite humbly telling us that her hit song “Hideaway” got her into the festival, Daya is arguably on fire. She has only one EP out, but many of her singles have gone viral and she has collaborated with artists like The Chainsmokers (“Don’t Let Me Down”). She drew an electric crowd for an impressive Saturday afternoon set. In the same slot the next day, Kali Uchis was powerfully radiant. Her stage presence was mesmerizing, so that by the end we didn’t only want to see her again—we wanted to be her. She, too, has collaborated with the likes of Diplo and Tyler, The Creator, and this year released her debut album, Isolation, which is getting attention.
Each night closed with huge headliners. The Weeknd, who was on the Grant Park stage which faces directly North, said he had never experienced such an amazing skyline view while performing. Complemented by the city lights, Lollapalooza onstage visual effects after sunset gave the festival a new look. Odesza’s dazzling video display cut in between close-ups of their synchronized drum brigade. Zedd’s trippy neon-light projections lit up the gleeful crowd.
It seems that looking down on Lollapalooza is trendy, at least in certain circles. And yes, the festival is more or less a mass gathering of North Side high schoolers with too much energy, too much glitter, and far too many substances. It’s hot as hell, it’s dense crowds, it's borderline dangerous mosh pit scenes, and it’s long lines for vomit-filled Port A Potties.
But it’s also really damn special, if only because of its scale. Playing Lollapalooza, which draws more than 100,000 people each day, is a huge deal for artists. For rising talent, just getting a stage is a sign of making it. For bigger artists, filling a field thousands and thousands of people deep helps cement their status in the music world as a star. For fans, this means the opportunity to see artists play intense, emotional, high stakes performances—back-to-back-to-back.
And for a few days, everyone forgot they were miserable.