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

SN_MeganThee-Stallion_LollaDay3-14 - Credit: Steven Nunez for Rolling Stone
Lollapalooza 2021 was packed with as much drama as one might expect from a massive festival during a pandemic. But it was also full of life-affirming musical moments. In the following we only present a selection of these happy 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 greatest moment came when Billy Idol casually danced on stage to join her on "Night Crawling" and a glowing joint cover of "White Wedding". An unannounced cameo that was so big without any hype as a preface left the crowd too stunned to react - but not for long. - NC
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Grandson Pep speaks the crowd
For those who were afraid of jumping into large crowds again at festivals, Jordan Benjamin (aka Grandson) delivered the ointment during his set on Friday. He reflected on the past year and reminded participants to be kind to one another. "You have no idea what the person next to you went through," he advised. He himself confessed that it had been an isolating year, adding that everyone feels rusty when it comes to going to festivals. He also joked that he was "damn tired of singing in the shower," as he and his band gushed a mix of rock, hip-hop and EDM, but it was just as easy for him to create an a cappella piece " Bury "Drop My Face Down." He also brought surprise guests. Chicago rapper Vic Mensa joined him on "Oh No !!!" perform. and later Jessie Reyez and Grandson performed "Rain," a song he wrote for the upcoming film The Suicide Squad. - AL
Tyler, the creator rises
Tyler, the creator, is no stranger to the festival circle, he even has his own: Camp Flog Gnaw Carnival. And on his last return to Lollapalooza, he headlined the main stage. Proved more than worthy, showcasing its various eras and paying tribute to its controversial past while still giving old school fans a taste of those early days. And he also brought a boat with him. "I was disgusting," said the rapper, thinking back to 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 most recent songs were highlights, but so were his delicate flower boy twists of “See You Again”, “911” and “Boredom” - when they were written before Covid, they sounded with the longing and loneliness befitting the time , and his Igor material was just as convincing ("New Magic Wand", "I Think", "Earfquake"). The die-hard were treated to some from his early goblin and wolf days, but it was Tyler's growth that really impressed. Tyler reminded critics that there can be redemption after adolescent ignorance. The decision to own it and come out as a better artist is a revelation. - AL
Machine Gun Kelly will perform a surprise set on the Bud Light Seltzer Sessions stage on the third day of the Lollapalooza Music Festival on Saturday, July 31, 2021 in Grant Park, Chicago. - Photo credit: Amy Harris / Invision / AP
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Amy Harris / Invision / AP
Machine gun Kelly flies in for a surprise set
Nestled in the heart of Grant Park is a small garden where Bud Light held reduced sessions for selected artists. Little did attendees know that Machine Gun Kelly wanted to be there on Saturday afternoon for a surprise performance just because. Happy fans who got there on 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 through the miniature speakers on the stage, but his screeching fans sounded the alarm that everyone else should rush there as soon as possible. - NC
Roddy Ricch recovers with assists from Polo G, Mustard
"Gosh, I screwed it up," laughed Roddy Ricch during "Down Below". The fans who flooded his stage on Friday seemed to forgive him. After all, from there it went on with the support of 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 teamed up with Mustard for "High Fashion" together. "Mustard also stayed on" Late at Night "and Roddy Rich's collaboration with the late Nipsey Hussle" Racks in the Middle ". He called Nipsey and also the late Pop Smoke when he performed her "The Woo". One song he dropped without addressing the collaborator was the mega hit "Rockstar" with DaBaby, which was scheduled to perform on Sunday before being dropped off from the festival just hours before the gates opened for the final day. Roddy ended up with his number one hit "The Box" twice and had the audience happily replay him to end his set. - AL
G Herbo performs at the Lollapalooza in Chicago. - Photo credit: Steven Nunez for Rolling Stone
Steven Nunez for Rolling Stone
G Herbo represents hometown with Chance the Rapper, DCG Brothers
G Herbo may have been a pinch hitter added to the official festival lineup at the last minute to fill in for Young Thug, who was nudged into a headlining slot instead of DaBaby on Sunday, but avid fans knew he was there where it belonged. He had already performed with Miley Cyrus on Thursday and previously played at the festival in 2018. He kindly took the seat and parted the space, putting the aspiring DCG Brothers in the spotlight to perform "Mmhmm". He also stressed the importance of all of us taking care of each other. "We need to normalize, de-stigmatize and talk about mental health," he said before dropping "PTSD," a song featuring the late Chicago rapper Juice WRLD, Lil Uzi Vert and Chance the Rapper. Chance joined him for the moving song, sending fans into an enthusiastic frenzy as they approached in the already crowded 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 haven't strayed far from the material they played on other past sets and featured their biggest hits - including “The Pretender”, “Learn to Fly” and “My Hero” - and that could have been exactly what festival goers needed. They also made it a family affair: they sang “Happy Birthday” for Grohl's daughter Ophelia and he and his daughter Violet delivered their cover of X's “Nausea”. Their performance offered a touchstone of normality, whatever that means in "Times Like These" (and with that, too, they opened their texts, which received new resonance in the Covid era). For two hours in an overcrowded field in Lollapalooza, it felt blissful, as if nothing had changed for long-time festival-goers: singing to favorite jewels with strangers, hearing Grohl's engaging stories, scurrying to the jams as if nothing else counted than the mood of a solid show. And for those fleeting moments, they didn't and offered a little escape before reality resumed. - AL
Ed Mavericks charm fans with Spanish love songs
Mexican singer-songwriter Ed Maverick is only 20 years old, but his songs are filled with the wisdom and heartbreak of someone well beyond their years. Back in the wee hours of Lollapalooza's first day, he was quick to swoon fans - especially those with Mexican flags around their shoulders - with his effortless guitar work and traditional, heartbreaking voice. Throughout the entire set of Maverick, both his music and stage banter were in Spanish only. Some viewers seemed unable to speak the language, others understood every word, but everyone was equally enthusiastic about his level-headed, emotional presentation. - NC
Flo Milli performs at the Lollapalooza in Chicago. - Credit: Sacha Lecca for Rolling Stone
Sacha Lecca for Rolling Stone
Flo Milli gets her big break
Flo Milli, the Alabama rapper who became a TikTok sensation, was relegated to the Grubhub stage, a medium-sized platform hidden behind trees, but that didn't stop her songs from attracting a crowd that was too close to the room was great. From “Beef FloMix” to “In the Party”, Flo Milli's verses often depend on a hyper-feminine flair and a catchy, chatty performance and are reminiscent of the sensations of the 2000s, Lil Mama and Kreayshawn. When she brought out "May I," a chewing gum hit reminiscent of gossip games in the schoolyard, the crowd streamed into the street and stood on tiptoe next to the chain link fence to rap along. Yes, you will need a bigger stage. - NC
Kim Petras heralds a new era with “The Future Starts Now”
The world takeover of Kim Petras is imminent. Hailed as America's first trans pop star, she put on a stadium-worthy performance at Lollapalooza 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," which sounded like a Daft Punk remix by Dua Lipa. If this teaser was any hint of what to expect from their next album, then Petras' new era is going to be smooth, bold, and stick on your mind all week. - NC
Megan Thee Stallion finally gets her "Hot Girl Summer"
Perhaps the most uplifting upsurge in hip-hop in the past two years has been that of Megan Thee Stallion. Unfortunately, she was forced to do a lot of this 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. Megan Thee Stallion was finally able to not only perform these hits for fans in person, but also experience the effect of her body-positive anthem in real time while people of all sizes danced along. - NC
Journey double down on the hits
No artist at this year's Lollapalooza was out as often as Journey, which explains why they nailed their big singles live. Occasional viewers waiting to hear "Don't Stop Believin" or "Any Way You Want It" received talented, melodramatic, amplified interpretations of the songs that were perfect for a festival. Journey has every right to get sick of these tracks after playing them repeatedly for over 40 years, but they looked proud to deliver their staples. Above all, singer Arnel Pineda pulled out all the stops and caused anyone who did not sing along to finally give in and go into full karaoke mode. - NC
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