From Machine Gun Kelly's Surprise Set to Journey, Here Are the Most Memorable Lollapalooza Moments

Lollapalooza 2021 was packed with about as much drama as one might expect from a massive festival held during a pandemic. Still, it was also full of life-affirming musical moments. Below, we present just a sampling of those joyful live performances.

Miley Cyrus Brings Out Billy Idol for “White Wedding” 
From back-to-back hip-hop guests to non-stop mega-hits, there was a lot to love about Miley Cyrus’ headlining set on the first night of Lollapalooza. By far the biggest moment came when Billy Idol casually waltzed onstage to join her for “Night Crawling” and a blistering joint cover of “White Wedding.” An unannounced cameo that massive without any hype to preface it left the crowd too stunned to react at first — but not for long. – NC

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Grandson Pep Talks the Crowd
For those who were anxious about jumping back into large crowds at festivals, Jordan Benjamin (a.k.a. Grandson) provided the salve during his set on Friday. He reflected on the past year and reminded attendees to be kind to each other. “You have no idea what the person next to you has been through,” he advised. He himself confessed it had been an isolating year, and added that everyone’s feeling rusty when it comes to festival-going. Plus, he was “fucking sick of singing in the shower,” he joked as he and his band exuberantly delivered a meld of rock, hip-hop, and EDM, but he was at equal ease dropping an a cappella “Bury My Face Down.” He brought out surprise guests, too. Chicago rapper Vic Mensa joined him to perform “Oh No!!!” and later, Jessie Reyez and Grandson performed “Rain,” a song he penned for the upcoming The Suicide Squad film. – AL

Tyler, the Creator Ascends
Tyler, the Creator is no stranger to the festival circuit, in fact, he has his own: Camp Flog Gnaw Carnival. And on his most recent return to Lollapalooza, he ascended to headliner on the main stage. He proved more than worthy, showcasing his various eras, and acknowledging his controversial past while still giving old-school fans a taste of those early days. And he also brought a boat for good measure. “I was gross,” the rapper said thinking back on his come-up. “I was nasty as fuck” and “ugly,” he recalled before delivering “Massa” from his latest acclaimed LP, Call Me If You Get Lost. His run of recent songs were highlights, but so were his tender Flower Boy turns of “See You Again,” “911,” and “Boredom” — while written before Covid, they resonated with the longing and loneliness that befit the times, and his Igor material was equally compelling (“New Magic Wand,” “I Think,” “Earfquake”). The die-hards were treated to a few from his early Goblin and Wolf days, but it was Tyler’s growth that really impressed. Tyler reminded critics that there can be redemption following youthful ignorance. Deciding to own it and coming out a better artist is a revelation. – AL

Machine Gun Kelly performs a surprise set on the Bud Light Seltzer Sessions stage on day three of the Lollapalooza Music Festival on Saturday, July 31, 2021, at Grant Park in Chicago.

Amy Harris/Invision/AP

Machine Gun Kelly Flys in for a Surprise Set 
Nestled away in the heart of Grant Park is a tiny garden where Bud Light hosted stripped-down sessions for select artists. Little did attendees know, Machine Gun Kelly planned to arrive for a surprise performance there on Saturday afternoon, just because. Lucky fans who arrived in time were treated to “My Ex’s Best Friend,” “Bloody Valentine,” and even a cover of Paramore’s “Misery Business.” The pop-punk rapper’s voice could only be carried so far by the stage’s miniature speaker setup, but his screaming fans sounded the alarm that everyone else should rush there ASAP.  – NC

Roddy Ricch Recovers with Assists from Polo G, Mustard
“My bad, I fucked up,” Roddy Ricch laughed during “Down Below.” The fans who flooded his stage on Friday seemed to forgive him. After all, things picked up from there with an assist from Chicago rapper Polo G, who had just performed on the other side of Grant Park, to deliver Polo G’s “Fame & Riches,” and later Roddy linked up with Mustard for “High Fashion.” Mustard also stuck around for “Late at Night” and Roddy Rich’s collab with the late Nipsey Hussle, “Racks in the Middle.” He shouted out Nipsey and also the late Pop Smoke when he performed their “The Woo.” One song he dropped without addressing the collaborator was megahit “Rockstar” with DaBaby, who was set to perform on Sunday before he was dropped by the festival mere hours before the gates opened for the final day. Roddy ended with his Number One hit “The Box” twice, letting the audience happily reprise it to close out his set. – AL

G Herbo performs at Lollapalooza in Chicago.

Steven Nunez for Rolling Stone

G Herbo Reps Hometown With Chance the Rapper, DCG Brothers
G Herbo may have been a pinch-hitter added last-minute to the official festival lineup to step in for Young Thug, who was bumped up to a headlining slot in place of DaBaby on Sunday, but adoring fans knew he was where he belonged. He had already performed with Miley Cyrus on Thursday, and he previously played the festival in 2018. He graciously took the slot and shared the space, giving the rising DCG Brothers the spotlight to perform “Mmhmm.” He also stressed how important it is that we all take care of each other. “We need to normalize, destigmatize and talk about mental health,” he said, before dropping “PTSD,” a song that features late Chicago rapper Juice WRLD, Lil Uzi Vert, and Chance the Rapper. Chance joined him for the moving song, sending fans into a delighted frenzy as they scrambled to get closer in the already packed area. – AL

Foo Fighters Comfort in Times Like These
Foo Fighters are veterans of Lollapalooza and a quintessential festival band. For the 2021 edition, they didn’t venture far from the material they’ve performed at other recent sets and featured their greatest hits — “The Pretender,” “Learn to Fly,” and “My Hero” among them — and that might’ve been exactly what festivalgoers needed. They also made it a family affair: for Grohl’s daughter Ophelia, they sang “Happy Birthday,” and he and his daughter Violet delivered their cover of X’s “Nausea.” Their performance offered a touchstone of normalcy, whatever that means in “Times Like These” (and they opened with that, too, its lyrics taking on new resonance in the Covid era). For two hours in a packed field at Lollapalooza, it blissfully felt like nothing had changed for longtime festivalgoers: sing-shouting along with strangers to favorite gems, hearing Grohl’s engaging tales, bobbing along to the jams like nothing else mattered but feeling the vibes of a solid show. And for those fleeting moments, they didn’t, providing a small escape before reality set back in. – AL

Ed Maverick’s Charms Fans with Spanish Love Songs 
Mexican singer-songwriter Ed Maverick is just 20 years old, but his songs are ripe with the type of wisdom and heartbreak of someone well beyond his years. During the early hours of Lollapalooza’s first day back, he was quick to make fans — especially those with Mexican flags draped around their shoulders — swoon with his effortless guitar work and old-spirited, heart-tugging voice. For the entirety of Maverick’s set, both his music and stage banter were strictly in Spanish. Some onlookers appeared to not speak the language while others understood every word, but everyone was equally enraptured by his cool-headed, emotion-forward performance. – NC

Flo Milli performs at Lollapalooza in Chicago.

Sacha Lecca for Rolling Stone

Flo Milli Gets Her Big Break 
Alabama rapper-turned-TikTok sensation Flo Milli was relegated to the Grubhub stage, a medium-sized platform tucked away behind trees, but that didn’t stop her songs from luring a crowd too large for the space. From “Beef FloMix” to “In the Party,” Flo Milli’s verses often hinge on hyper-feminine flair and catchy, conversation-style delivery, recalling 2000s sensations Lil Mama and Kreayshawn. By the time she bust out “May I,” a bubblegum hit reminiscent of schoolyard hand-clapping games, the crowd spilled out onto the street and stood tip-toed by the chain-linked fence to rap along. Yeah, you’re gonna need a bigger stage. – NC

Kim Petras Kicks Off a New Era With “The Future Starts Now” 
Kim Petras’ world takeover is imminent. Hailed as America’s first trans pop star, she put on a stadium-worthy performance at Lollapalooza complete with explosive singles, smoke-filled lasers, and impeccably well-choreographed dancers. To open the set, she debuted an upcoming song called “The Future Starts Now” that sounded like a Daft Punk remix of Dua Lipa. If this teaser was indicative of what to expect from her next album, then Petras’ new era will be slick, bold, and stuck in your head all week. – NC

Megan Thee Stallion Finally Gets Her “Hot Girl Summer” 
Arguably the most uplifting glow-up in hip-hop over the past two years has been that of Megan Thee Stallion. Unfortunately, she was forced to do much of it online or in quarantine. The Houston rapper became an unstoppable force thanks to the one-two punch of “Savage” and “WAP,” but before that, it was “Hot Girl Summer” that put her in the spotlight. At long last, Megan Thee Stallion not only got to perform those hits for fans in person, but she also got to watch the impact of her body-positive anthem in real-time as people of all sizes danced along. – NC

Journey Double Down on the Hits
No artist at this year’s Lollapalooza has been around the block as many times as Journey has, which explains why they nailed their big singles live. Casual onlookers waiting to hear “Don’t Stop Believin’” or “Any Way You Want It” were gifted melodramatic, amped-up renditions of the songs that were perfect for a festival. Journey have every right to feel tired of those tracks after playing them on repeat for over 40 years, but they looked proud to deliver their staples. Singer Arnel Pineda in particular pulled out all the stops, prompting anyone who wasn’t singing along to finally cave in and go full karaoke mode. – NC

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