Miley Cyrus, Jimmy Eat World, and More

Lollapalooza has returned, a delight to fans and a test for public health officials. The beloved Chicago music festival is requiring proof of negative COVID-19 status for entry, and attendees certainly enjoyed the freedom this implied. Day one carried some of the manic energy of a party for the end of the world, as bewildered parents chased packs of feral youths,  over-indulgers stumbled about like broken toys, and even veterans of the festival circuit found themselves swept up in the optimism. Live music is back.

For the 30th anniversary edition of the festival — founded by Perry Farrell in 1991 — the exuberance could be witnessed both offstage and on. Rising artists like Flo Milli and Paris Texas made their triumphant Lollapalooza debuts, beloved veterans Jimmy Eat World celebrated 20 years of their landmark album Bleed American, and Miley Cyrus brought down the house in a headlining performance. Check out some of the most memorable moments below.

– Wren Graves

Aly & AJ Wished Lollapalooza a Happy Birthday

“We want to thank Perry Farrell for starting this whole fucking thing 30 years ago,” sisters Aly & AJ said. “Happy 30th fucking birthday.” From there, they launched into their 2007 smash hit “Potential Breakup Song,” which has seen a surge in streams over the last year on TikTok. It was a joyful way to welcome fans to the festival. – Wren Graves

Almost Monday Chased Away the Clouds

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Almost Monday, photo by Jen Vesp

“Man this is crazy!” Standing on the Grubhub stage in a slouchy blue suit and a pair of wayfarers, Almost Monday frontman Dawson Daughtry sounds like he means it. The rising San Diego alt-pop trio might have a touch of “aw shucks” attitude, but they brought nothing but pop professionalism to their early afternoon set. The band massed a respectable crowd, given the time of day, and chased away the day’s early clouds with factory-fresh renditions of favorites like “Hailey Beebs” and “Broken People,” as well as new tunes such as the situationally appropriate “Sunburn.” – Tyler Clark

Orville Peck Proved Masks Will Always Be Cool

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Orville Peck, photo by Jen Vesp

Peck was a vision in black, white, and red, and while hs trademark mask may not meet CDC guidelines, hot damn did it look cool. He swayed with his guitar and slapped the piano like it had insulted his mother, and when he covered Lady Gaga’s “Born This Way,” his deep voice could make your jawbone vibrate. The set ended with a virtuosic whistling display for the dance floor. – Wren Graves

Flo Milli Exceeded the Hype

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Flo Milli, photo by Jen Vesp

It’s a Lollapalooza tradition: Each year, there’s at least one artist who gets inexplicably booked at a smaller stage than their hype demands. This year, that dubious honor goes to Flo Milli, whose fans jammed the secluded Grubhub stage for the Alabama rapper’s high-energy set. Bolstered by raucous renditions of Tiktok hits “Beef FloMix” and “In the Party” and brassy cuts from 2020 debut Ho Why Is You Here, Flo Milli’s set was easily the best attended of the early shows. It was also the most compact, ending with 30 minutes still left on the clock. – Tyler Clark

Jimmy Eat World Leaned into the Weird

“The last time we played in front of people was December 12, 2019,” said Jimmy Eat World frontman Jim Adkins. “If it’s gonna be weird you might as well lean into weird and play Lollapalooza.” Despite the layoff, the Arizona emo icons showed no signs of rust, plowing through spirited renditions of favorites old (1995’s “Lucky Denver Mint”) and new (2019’s “All the Way (Stay)”). The biggest pops came for songs from 2001’s Bleed American, which turned 20 this week (apologies to all elder millennials who had to read that). By the time they hit the end of closing trio of “A Praise Chorus,” “Sweetness,” and “The Middle,” it didn’t matter if the nostalgia was real or borrowed. – Tyler Clark

Paris Texas Brought the Bounce

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Paris Texas, photo by Jen Vesp

Paris Texas had the crowd rippling from their first drop of the beat, as the duo charged and jumped across the stage. Their energetic performance took it’s toll. “I did not plan to make that song this long,” Louie Pastel quipped, while Felix kept repeating “Oh my God, Chicago!” And yet every time the next track began, they revved all the way back up to overdrive. – Wren Graves

All Time Low Fought the Venue

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All Time Low, photo by Jen Vesp

Longtime Lollapalooza attendees know that Grant Park’s Petrillo Bandshell (home of the Tito’s stage) has a habit of swallowing even the gamest of bands. The latest victim? Long-running Maryland emo band All Time Low, whose jokey banter and aughts favorites like 2007’s “Six Feet Under the Stars” and “Dear Maria, Count Me In” couldn’t quite overcome the notoriously dodgy sound quality. Throw in the set’s dinner-hour timeslot, and you have a recipe for a crowd more interested in making plans for later than enjoying the music at hand. – Tyler Clark

Playboi Carti Never Found a Groove

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Playboi Carti, photo by Jen Vesp

Playboy Carti danced his tush off and had just enough breath left over for every 10th word of his songs. During the numerous pauses, he first complained about how spread out everyone was, and then asked the crowd to settle down and back up. At one point he departed the T-Mobile set and climbed on a structure along the side of the stage for a brief and strange interlude. When he came back, he ended every song by walking to the edge of backstage and having an inaudible conversation with a small group of people. It wasn’t what you’d call smooth, but that didn’t stop his fans from shouting along with every word he missed. – Wren Graves

KAYTRANADA Broke the Heat

After a day of broiling sun and tropical humidity, the temperatures at Lollapalooza finally broke as the sun went down. A chilled-out sunset called for some chilled-out tunes, which is exactly what Canada’s KAYTRANADA provided during his hour on the Bud Light stage. Drawing from his own catalog as well as his “KAYTRANADA Edition” remixes of artists from Chance the Rapper to Rihanna, the DJ and producer did exactly what he needed to: gave everyone a chance to catch their breath before one last wild push to the headliners. – Tyler Clark

Kim Petras Wanted to See Some Fucking

In one of the most tightly choreograpped sets on Thursday, Petras kept up a lively banter from the stage. “Any rich guys in the crowd wanna buy me shit?” she asked, eliciting numerous volunteers. Later, she announced, “I want to see some fucking in the crowd tonight. Let’s see some tits too, that would be nice.” It was a passionate performance from an artist who was clearly happy to be there. “I missed you bitches,” she said. “I’m gonna cry.” – Wren Graves

Oliver Tree Excelled with Spectacle

While the rest of the festival headed for Miley, Illenium, and Steve Aoki, a small-but-passionate crowd of Very Online diehards camped at the Grubhub stage for the evening’s most memeable act. To borrow a page from Stefon, Oliver Tree’s set had it all: persona changes, a big-ass alien, an even-bigger-ass guitar, flying wigs, stage combat… well, you get the idea. The (very good) bit aside, Tree also showed off his unironic musical chops, treating fans to renditions of “Cash Machine,” “Miracle Man,” and other cuts from 2020’s Ugly Is Beautiful. Tree’s crowd might’ve been the smallest of the night’s headliners, but those in attendance might’ve seen the night’s most entertaining show. – Tyler Clark

This Is Miley Cyrus’ Party and She Can Do What She Wants

Dark sunglasses at night? A bonkers medley of “We Can’t Stop” and Pixies’ “Where Is My Mind?” Singing straight into the camera and spitting on it? The surprises never cease with Miley Cyrus, who has matured alongside her audience and become one of the most exciting acts in music today. Her star-studded set included appearances by Billy Idol, G Herbo, Juicy J, and more, as well as graphics of skeletons 69-ing on a motorcycle, a display of handcuffs that read, “Free Britney,” and a tasteful collection of covers that spanned many genres and times. “I’m so sick of trying to feel something through a fucking screen,” she told the crowd. The screams in response were loud enough for half of Chicago to feel it. – Wren Graves


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