Lollapalooza 2021 reviews, Day 1: Miley Cyrus, Black Pumas, Orville Peck, Playboi Carti, Steve Aoki, Jimmy Eat World

Headliner Cyrus welcomes a parade of collaborators — from G Herbo to Billy Idol — to sing as she sermonizes, sells merch and stands up for the #freebritney cause.

SHARE Lollapalooza 2021 reviews, Day 1: Miley Cyrus, Black Pumas, Orville Peck, Playboi Carti, Steve Aoki, Jimmy Eat World

Miley Cyrus closes out Thursday night at Lollapalooza.

Tyler LaRiviere/Sun-Times

Here’s a roundup of some of the sets at Day 1 of Lollapalooza 2021 in Grant Park:

Miley Cyrus

Starting her Lollapalooza headlining set with “We Can’t Stop” (preaching the general theme of “it’s my party and I’ll do what I want to”), Miley Cyrus set the tone early on: It would be one helluva time and she would be making all the rules. In following those two tenets, the genre-bending star dominated the festival’s opening night.

There were fireworks, some memorable covers, a motley crew of guests, moments of nearly flashing the videofeed cameras, and the artist taking a stand on the importance of freeing Britney Spears. During Cyrus’ performance Thursday of her hit “SMS (Bangerz),” which features Spears, the jumbo screens next to the stage broadcast the trending #freebritney message superimposed with caricatures of handcuffs. (Cyrus recently championed Spears’ conservatorship emancipation at a show in Vegas too.)

Earlier in the performance, Cyrus — keen on doing covers lately — dished out a few tributes to songs that she said “made me who I am.” Among them were Blondie’s “Heart of Glass,” the Pixies’ “Where Is My Mind?,” Temple of the Dog’s “Say Hello To Heaven” (which she performed at a Chris Cornell tribute concert a few years ago) and a duet with special guest star Billy Idol on “White Wedding.”

The two also ran through their collaborative track “Night Crawling,” featured on Cyrus’ latest rock-leaning album “Plastic Hearts.” Other guest stars included G Herbo, followed by Wiz Khalifa and Juicy J (plus a random appearance by Benny the Bull) for their track “23” and Kid LAROI for the duo’s new song “Without You.”

Beyond the blitzkrieg of star wattage, Cyrus took moments to get philosophical too, pondering what the quarantine taught her, saying “it was humbling to be humanized together … experiencing the last year and a half with no division between us, all knowing the pain of being disconnected and the value of having one another in our lives,” before cracking a joke about her red sequined jumpsuit being custom made by Gucci and flown in from Italy.

Her bandmates also wore her own merch, the ensemble all standing in front of a banner that read “Sell Out to Sell Out.” Cyrus continues to be that perfect dichotomy of pop star kept at arm’s length and a “they’re just like us” celebrity who keeps everyone guessing.— Selena Fragassi

Black Pumas

Though the Black Pumas set ended predictably with the band’s giant hit “Colors” that has been ubiquitous in recent months (including placement in a Target commercial), what was not expected was the overwhelming wash of emotion that came over the crowd. Even frontman Eric Burton (wearing a David Bote Cubs jersey and hat) had to pause and collect himself watching the sea of hands in the air loudly applauding during a break in the performance.

“Cut it off,” he instructed the band, including his partner in the project, the exemplary guitarist Adrian Quesada, whose jam-session solos had been near transcendental to this point. “It’s just you and me,” Burton said, his attention turning to the crowd as he jumped down on the ground and shook people’s hands in the front row, his greetings to each person audible in the microphone.


Eric Burton left the stage for some of the Black Pumas set at Lollapalooza.

Tyler LaRiviere/Sun-Times

The moving song, with its Sam Cooke ambitions to inspire social change, was a tangible game changer in the day, literally bringing people together after nearly two years apart. As Burton sang the last line of the song a capella, the crowd joined in as a last-minute choir that made it one of the highlights of the day.

Elsewhere in the set, after a back-to-back deliverance of the band’s hit “Fire” followed by a rousing cover of Leon Bridges’ “Smooth Sailing,” Burton shared the story of how he went from being a street busker in Austin, Texas, to being on the cover of magazines and nominated for Grammys. That humility and authenticity came through impressively in this set, his passion shown in his octave-busting wails and his joy seen as he moved around the stage dancing with nearly everyone in sight.

The Black Pumas are often categorized as a revival music act — and no doubt they hark back to a time of James Brown, Otis Redding and Marvin Gaye — but it’s their revival of the human spirit and connection to important values that is most needed in the world right now. — Selena Fragassi

Steve Aoki

There are a number of elements you can expect in a typical Steve Aoki performance — pyrotechnics, special guests, bass drops and cake throwing, to name a few.

That’s largely why the EDM giant’s Thursday night set at Solana X Perry’s Stage felt like stepping into a time warp to a pre-2020 period, one where thousands of screaming, jumping fans packed tightly at an EDM concert didn’t leave you worried about health risks amid a global pandemic.

There was a sense throughout the night that, despite the threat of COVID-19, concertgoers either felt confident in Lollapalooza’s new admission protocols, compartmentalized the risks to just have fun or went hard in spite of the pandemic and all that’s been lost throughout 2020 and 2021.

Regardless of the context, Aoki stuck to his familiar formula and gave a strong performance comprised of original tracks and remixes that had the entire crowd dancing consistently throughout his hour-and-fifteen-minute set.

He had fire and smoke shoot from the stage.

He brought out several special guests, like All Time Low’s Alex Gaskarth — and Darren Criss of Glee fame, who performed a mystifying cover of Dave Matthews Band’s “Crash into Me.”

He had a bass drop in just about every song he blazed through in his Serato, which spanned multiple genres to include everything from Daddy Yankee’s “Gasolina” to Eurythmics’ “Sweet Dreams.”

And he threw multiple cakes into the crowd, asking “Who came here tonight to have cake all over their face?” before lobbing one into a lucky fan’s face.

Aoki had complete control over the crowd and demonstrated a distinct ability to connect with the seemingly endless sea of faces. He gave his fans exactly what they wanted and they responded enthusiastically to every effort he made to hype them up.

When he raised his arms like a puppet master, the crowd followed his motions. When he popped bottles of champagne, they clamored to be spayed with the bubbly. When he led them in a singalong of Céline Dion’s “My Heart Will Go On,” they belted out every word until it progressed into a buildup and eventual bass drop.

There is no wind-down in a Steve Aoki set and his final songs of the night pushed the crowd into an even higher level of euphoria, which hadn’t seemed possible after seeing the way they responded when he played his BTS collaboration “Waste it on Me” and his remix of Panic! At the Disco’s “I Write Sins not Tragedies.”

His nearly 12-year-old remix of Kid Cudi’s “Pursuit of Happiness” came second to last and elicited perhaps the biggest response from Lollapalooza fans, some of whom sprinted from wherever they were on the festival grounds and into the crowd to catch the song.

Fans of all ages danced passionately straight into the end of his set, as Aoki smiled and moved from behind his DJ setup to the edges of the stage, jumping up and down with them. — Matt Moore

Orville Peck

Orville Peck preforms at the T-Mobile Stage Thursday.

Orville Peck performs Thursday at Lollapalooza in Grant Park.

Tyler LaRiviere/Sun-Times

Orville Peck may have been the only one wearing a mask at Lollapalooza on opening day, but his faithful crowd (quite substantial for the early afternoon set) did come decked out in cowboy hats. Peck, a mysterious and unidentified Canadian artist who is turning modern country on its head and taking great advantage of country’s current moment, has a shtick of wearing a long, fringed facial covering for every performance. He looked every part old-school Nashville in his accompanying fringed vest and sequined chaps while brandishing a classic Gretsch guitar, quickly moving over to the piano for his rollicking set.

Songs “Big Sky,” “Legends Never Die” (his memorable duet recorded with Shania Twain) and “Drive Me Crazy” (“about truck drivers and love”) from his acclaimed EP “Show Pony” deftly blurred the lines between country twang, indie rock and even some added psychedelic swag.


Eva Adams (lifting hat) and Bridget Brazil cheer during the Orville Peck performance.

Tyler LaRiviere/Sun-Times

“Hello I’m Orville Peck,” he said, conjuring the ghost of Johnny Cash to open the set, and then proceeded to show off his deep baritone, a bat signal for his many followers who sold out his pre-show Wednesday at Thalia Hall. There’s a part of Peck’s rise that feels very Gaga-like (he also wisely offered up his cover of “Born This Way” on Thursday). From the garish costume choices to the pseudonym to becoming a beloved LGBTQ icon, his career seems poised to reach that pinnacle in due time. Watch out for this one, mask and all. — Selena Fragassi

Playboi Carti


Playboi Carti performs Thursday at Lollapalooza.

Tyler LaRiviere/Sun-Times

The returning Lollapalooza crowd might not have been ready for Playboi Carti, and the rapper didn’t appear ready for them either. The headline-making hip-hop star drew a large throng of people, and as a result, his disjointed set was marred by constant stops and starts as Carti pleaded with the crowd to step back and open up some personal space, after a number of people began passing out. Not a first for Lollapalooza by any means, but in these times, the idea of people suffocating each other takes on a whole new dismal tone.

Carti for his part was wearing a mask, though it was likely more part of his off-kilter ensemble than any functional purpose. The accessory did not help his set, though, which often came off muffled (even by mumble-rap standards) as he ran through what felt like one long track with identical sampling. Among the highlights was “Go2DaMoon,” his track recorded with Kanye West, but overall the performance lacked the panache we’ve come to expect from the artist, and at times he seemed to lose himself in the magnitude of the stage, which was just begging for guest stars. — Selena Fragassi

Jimmy Eat World

Jimmy Eat World barreled into its set with a guitar solo that led straight into the band’s 2004 single “Pain.” It was enough to get concertgoers funneling off South Columbus and into the larger crowd of fans rocking out in front of the Bud Light Seltzer stage. “It’s so good to be back,” lead singer and guitarist Jim Adkins said.

Eventually, the energy that permeated the crowd for the first couple of songs plateaued as the band moved into the rest of the hourlong set and played more songs from its nearly 28-year discography. A few slower-tempo songs were met with a muted crowd response. And while there may have been a few off notes, they ultimately added to the band’s presence as a seasoned, foundational and tight unit that has fun and will never give an identical performance.

The set ended with songs from the beloved album “Bleed American,” which turned 20 years old last week. The shift into “Sweetness” followed by “The Middle” fully jolted the crowd to life, with people dancing and singing, ending the set on a high note. — Matt Moore

Flo Milli


Flo Milli performs Thursday at Lollapalooza in Grant Park.

Tyler LaRiviere/Sun-Times

When Flo Milli stepped onto the stage for her Thursday afternoon Lollapalooza set, it was clear she came to do one thing: rap her heart out.

Devoid of backup dancers, a D.J., flashy visuals or any of the other staples artists use to hype crowds, she commanded the stage alone with a blistering set that practically ignited the thousands of fans packed in tight to see her in the excruciating heat.

The 21-year-old Mobile, Alabama, native strutted across the stage, blazing through select tracks from her 2020 mixtape “Ho, Why Is You Here?,” putting her whole chest into every line and the crowd shouted each word back to her. She wasted little time talking in between songs, making the pace of her set feel almost identical to the hit parade that is her mixtape.

What’s notable about the mixtape is Flo’s lack of melodic hooks — she opts instead to repeat extremely memorable and catchy lines. This translated really well live. For the majority of the songs she performed, she rapped without a backing vocal track on the verses, then let the vocals accompany her on the chorus, serving as an invitation to the fans to participate‚ and they did loudly. It flexed her prowess as one of the most talented hip hop artists in the game.

By the time she went into her song “In the Party,” the already high-energy crowd turned up even higher, prompting her to hop off the stage and into the front row.

But after a blistering 25 minutes, which included a brief snippet of her feature on Yung Baby Tate’s “I Am,” the set ended, cutting off what was scheduled to be a 45-minute slot. The crowd didn’t seem to mind, though.

We can’t wait to see Flo again on a bigger stage with more material. — Matt Moore


A solitary beat reminiscent of a pulse pounded from the speakers as Grammy Award-winning producer Kaytranada stepped in front of the crowd. It was a fitting entrance because as soon as he dropped his first beat, he brought life to the area, with some fans packed as close to the stage as they could get while others opted to dance on the outskirts.

The man, as smooth as his production, sipped from a bottle of wine and danced along with the steady grooves as the sun dipped behind the skyline.

He masterfully pieced together songs from his albums “99.9%” and “BUBBA,” in addition to remixes and collaborations, all while hyping the crowd with encouragement on the microphone. It showed his dexterity as both a producer and a performer.

Savvy, too, were his repeated references to Chicago artists. This included dropping Chance the Rapper’s “All Night” and Kaytranada’s Mick Jenkins-featuring “Gray Area.” Add to that the remixes of songs from artists like Kelela and Rihanna.

It all worked to get the crowd smiling and dancing, ready to face the rest of the first night of Lollapalooza. — Matt Moore

Ant Clemons

It’s amazing that Ant Clemons isn’t a household name yet. Kicking around since 2016, he’s primarily been a songwriter, the Oz behind a curtain of top singles for acts like Beyonce, Camilla Cabello and Chicago’s own Kanye West, with whom he worked on the 2018 track “All Mine.”

Clemons introduced that song in his set as one that changed his life “when a gentleman from Chicago picked a poor young man up off the floor,” and then proceeded to give a sampler-platter medley of his other big numbers as a way to “get to know” him. That included H.E.R.’s “Damage” (followed by an audio snippet of her winning a Grammy) and “Better Days,” the track he did with Justin Timberlake and that both performed at President Joe Biden’s and Vice President Kamala Harris’ inauguration in January.

Early in the set, Clemons also dropped a bomb with what is presumed to be the live debut of his new song “Appreciation” featuring Ty Dolla $ign, that he announced would drop at midnight Thursday night. If his previous work — like the EP “Happy 2 Be Here,” nominated for a Grammy this year — is any indication, expect his new music to make just as much of a dent and usher in his prime-time appearance at the next Lollapalooza. — Selena Fragassi



Singer-songwriter LP performs Thursday at Lollapalooza.

Amy Harris/Invision/AP

Like Ant Clemons earlier in the Day, LP is an artist that got to come into their own on the Lollapalooza grounds. Though they spent decades logging hits for Cher, Christina Aguilera and other pop stars, the demure singer-songwriter, real name Laura Pergolizzi, showed off the writing chops that kickstarted their career and reportedly sparked a bidding war between labels early on. Alongside a versatile backing band, LP offered a canon of trademark catchy material, including “The One That You Love,” “Girls Go Wild” and “When We’re High.” Though the vocals carried incredibly throughout the park (making one wonder if LP even needed the microphone), the strength of the performance wasn’t enough to draw a huge crowd to their flame. Intimate venues, like the pre-show LP did Wednesday night at Metro, are the way to see them. — Selena Fragassi

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