There was a unique energy in downtown Chicago over the weekend, as thousands of fans made their way across Grant Park to Lollapalooza. For many, it was the first time experiencing live music since March 2020, when most concerts were shut down due to COVID-19. Though there have been recent concerns over the safety of festivals in the face of rising caseloads, the news didn't put a damper on the crowd or the performances, as Megan Thee Stallion, Miley Cyrus, and more delivered impressive sets across the four-day event. Ahead are a few of the best ones we saw:
Miley Cyrus' star-studded set
@vijatm Miley Cyrus at Lollapalooza 2021
Miley Cyrus' two-decade run in the spotlight — from the Hannah Montana early aughts to her more recent turn as cover-singer-in-chief — hit another milestone over the weekend when she headlined Lolla's opening night. Decked out in a bedazzled candy-red Gucci jumpsuit, Cyrus showcased a setlist that spanned every era of her genre-hopping career, including crowd-pleasing Disney-friendly hits "The Climb" and "Party in the USA" and her recent pop-rock anthem "Plastic Hearts." Meanwhile, performances of "Night Crawling," with special guest Billy Idol, and "23," with appearances by Wiz Khalifa and Juicy J, were a reminder of the star-studded list of collaborators Miley casually keeps in her back pocket. In between tracks, she gave insightful, introspective speeches, touting the strength that is getting us all through these tumultuous times. She also noted that "there's light at the end of the tunnel, and Lollapalooza is that light" — a statement that feels shakier by the day.
Olivia O'Brien's honest, curse-laden hour
"First big festival back and the first day so let's have the best f--ing day!" shouted Olivia O'Brien during her afternoon performance. The pop singer followed through on her end, with impassioned performances of her bilateral ballad "hate u love u" and viral TikTok hit "Josslyn." Later, she apologized for messing up a few of her lyrics, and gave blunt commentary over the sweltering Chicago heat, all while sipping on a seltzer: "It is f---ing hot, what the f---ing s—t?"
Flo Milli caters to the crowd
The Alabama MC brought her infectious "ho, Flo Milli s—t" catchphrase along with fan favorites "Beef FloMix," "Like That B---h," and "In the Party" to her high-energy Lolla set. She also added a little visual flare to the proceedings, as images of iconic Black women like Tiffany Pollard and Nene Leakes, along with shots of the burn book from Mean Girls and the Clovers cheerleaders from Bring It On, flashed across the screen.
Aly & AJ's big moments on a small stage
Both Gen Z and millennial fans turned out for sister act Aly & AJ — who, like Cyrus, got their start on the Disney Channel — as well as the duo's laid-back acoustic set at the more intimate Toyota Music Den later in the day. The smaller setting proved to be the perfect place for the siblings to showcase their new alternative tunes "Slow Dancing" and "Lost Cause" with a level of comfort that only comes when artists truly believe in the music they're creating. The big (and obvious) highlight, though: when Aly began to play the first few notes of their hit "Potential Breakup Song" on a small electronic keyboard.
Kim Petras' choreo-filled kiki
Kevin Mazur/Getty Images Kim Petras at Lollapalooza 2021
Kim Petras began her electric set at level 100, commanding the stage with elaborate choreography and R-rated quips (to wit: "I wanna see some f--ing in the crowd tonight"). The pop singer had a genuine desire to entertain the crowd, and she put in the work to do so on songs like "I Don't Want It at All" and "Heart to Break," along with Charli XCX's electro-pop anthem "Unlock It," which Petras is featured on.
Megan Thee Stallion takes (and shakes) the cake
Scott Legato/Getty Images Megan Thee Stallion at Lollapalooza 2021
Grammy winner Megan Thee Stallion's Hot Girl Summer proclamation came to life as soon as she hit the stage on Saturday. Donning a revealing one piece — complete with rock band logos of AC/DC, Kiss, and the Rolling Stones — along with fishnet stockings, the Hot Girl Coach delivered her usual blend of cool confidence and swagger. Meanwhile, the crowd indulged Megan's come-ons, dancing along with the Houston rapper as she rapped (and did the corresponding viral TikTok moves to) her hits "Savage," "WAP," and "Thot S--t." She also twerked, tongue-popped, and asked the crowd to repeat "If you're a hot girl make some noise!" They were happy to oblige.