Text and Images by Gaby Deimeke
Lollapalooza 2021 was, to put it lightly, the social and musical rebirth of the summer. Nothing quite compares to jumping up and down with a bunch of sweaty strangers to the song of the summer at a music festival, and it was just what we all needed.
This year, Lolla gave us all that and more. After a year of deprivation from music festivals, folks were ready to show off their style and get wild. Here are some of our top moments from Lollapalooza 2021 in Grant Park, Chicago.
Thursday Highlights
Up-and-coming pop singer-songwriter Christian French kicked off day one with an early afternoon set, as well as playing a smaller, more intimate set at the Bud Light Seltzer Sessions stage, where he played an acoustic version of his song Avalanche.
The park slowly started filling up as folks trickled in, wearing their best festival outfits and ready to have fun. It was a collective breath of fresh air as festival goers set up blankets to watch afternoon sets, hung out by the Perry’s sign to meet up with their friends, and even had some group naps in between the music.
Rock and roll power duo Migrant Motel played at the Toyota Music Den, where fans were cooling off and getting free prizes like a Lolla bandana and cotton candy.
Musicians such as Ashe and Olivia O’Brien mentioned in their sets that this is their first show back post-pandemic. It was meaningful to Ashe that she could kick-start live music at Lolla. Ashe said, “After this past year, I’m coming back to a completely different career, at Lollapalooza, which is insane. This is the coolest festival. It’s the one.”
California girls Aly and AJ, wearing Giuliva Heritage suits, performed a cover of The National’s I Need My Girl, which they released this weekend. You can listen to it here.
“Being on stage at Lollapalooza completely encapsulated everything Aly and I love about live music,” said AJ. “An incredible band behind us, great visuals and a killer crowd. It was more than we could’ve ever imagined. We’ll never forget it.”
Other fan favorite sets for the day included MAX, Orville Peck, Kaytranda, Kim Petras, Oliver Tree and Steve Aoki, who of course threw cake into the crowd during his set.
Miley Cyrus closed the show, wearing a sparkly red Gucci suit and playing a string of hits–Wrecking Ball, We Can’t Stop, and The Climb–as well as tracks off her latest album Plastic Hearts. She also brought out a bunch of surprise guests, from Billy Idol to Wiz Khalifa to The Kid Laroi, with whom she performed her current chart-topping hit Without You. She even brought out the Chicago Bull mascot.
Friday Highlights
LollaLand started off strong on Friday, with Jake Wesley Rodgers kicking things off at the BMI stage. He’s reminiscent of a young Elton John and put on a lively show, playing piano and strutting around stage.
Fans were ready to put on their cute outfits and get Friday going. There were lots of sparkles, fishnets, neon and ‘90s vibes around the festival this year.
There was also Tyler the Creator’s bright yellow GOLF clothing pop up near Buckinghim fountain that was a popular merch choice for fans.
Tai Verdes opened the Bud Light Seltzer stage and got the crowd hyped, playing a string of melodies that made him famous on TikTok during the pandemic, including Drugs and Stuck In the Middle. The crowd loved it.
Emotion-filled musician Grandson brought out special guests Vic Mensa and Jessie Reyes during his time on the Lolla stage. He and Jessie performed the theme song they wrote for the upcoming Suicide Squad movie to end his set.
Chowtown, a huge row of food stands cascading down Columbus Drive, had all the food options anyone could crave, from cheese fries to ramen to tacos to ice cream and coffee if you need a quick sugar rush. Toyota was also giving away free green apple cotton candy, which was a big hit, and the Cupcake Vineyard was giving away free frozen drinks with the image of your selfie on top!
Lauv took over the evening hour and got the crowd excited with his hits I’m so Tired, Paris in the Rain and Drugs and the Internet. He wore a custom Farradas Knits suit made of knitted patchwork fabric. You can check out more of their work here.
Other notable sets from Friday included Jacob Banks, Elohim, Jack Harlow, Omar Apollo, who closed out the Grubhub Stage, and Tyler the Creator, who closed out the T-Mobile stage. He had a full size boat on stage, which he even hopped in to perform a few songs, a bellhop costume with a luggage cart that he started the show with, and custom clouds that floated down. The production quality was unmatched.
Saturday Highlights
Day three continued with a huge list of high-profile musicians, and showcased the variety and powerful entertainment that Lollapalooza truly is. The early afternoon started with a huge list of up-and-coming musicians, and then transitioned to all-star headliners such as Post Malone and Megan Thee Stallion.
Over 100,000 people attended Lolla day 3 this year, which means we saw everything from dyed hair, piercings, fishnets, crop tops, swimsuits, combat boots and more.
Rising singer/songwriter Tate McRae performed two sets on Saturday, one at a main stage, and a smaller acoustic set for her diehard fans. Tate said before her performance, “It means the world to be performing at Lollapalooza this year. So many of my idols are going to be there and I seriously cannot wait to feel the energy of the crowd. It’s going to be amazing being with people again.”
Viral TikTok musician Jessia opened the Bud Light stage, telling the crowd that not only was it her first music festival she’d ever performed at, but it was the first music festival she had ever been to. She played an Avril Lavigne cover, as well as her viral song, I’m Not Pretty, to fans who were lounging on blankets and resting up before the hot day ahead of them unfolded.
Notable mid-day sets were Trevor Daniel, who performed his hit song Falling to a huge crowd in the afternoon, after a few microphone issues that were eventually fixed, and Bia, who had some awesome dancers supporting her for her performance. She finished her set with her vibey summer jam Whole Lotta Money, and everyone was cheering along.
Up-and-coming musician Jason Singer, known by his stage name Michigander, played his indie songs at the Grubhub stage. Hailing from Detroit, he brought a midwest humbleness to the set, and mentioned that he thought only a handful of people would show up. To his surprise there were hundreds of folks at his afternoon set.
There was lots of pyro and production to go around on Saturday, with Vintage Culture getting Perry’s stage hyped for the evening with some fire and smoke. Lost Kings followed immediately after and continued the party, getting the crowd very excited with their remixes and huge EDM drops. Machine Gun Kelley also performed a surprise set in the evening, which was a fan favorite.
Megan Thee Stallion’s performance was highly anticipated by fans in the crowd, and it delivered thorough and through, with Megan bringing the twerking and tongue-out confidence to the T-Mobile stage as the sun was setting on day three. The crowd sang along and cheered her on during her singing and butt-shaking her way through a string of hits, especially Hot Girl Summer and Savage.
Journey, Post Malone, Marc Rebillet and Slander all closed out Saturday night–a stellar lineup and impressive feat by Lollapalooza to bring so many all-star performers together. Posty brought out special guest Tyla Yahweh for their song Tommy Lee, and made sure there was lots of fire and fireworks to keep the energy high.
Illenium had the EDM crowd vibing to their emotional synth, getting everyone to sing along during Superhuman. The crowd left satisfied after another day of incredible music and comradery in Chicago, and walked out onto the streets in unison, ready for one final day of organized chaos.
Sunday Highlights
Bumble had an activation at the fest called The Hive, where folks could hang out, take photos, and get a free prize if they showed the Bumble app on their phone. They also sponsored Brooke Alex’s performance at Lolla, in an aim to help gender inequality within the music industry.
Brooke Alexx said, “It is such an honor to partner with a company like Bumble for my very first music festival performance. Festival lineups are largely male-dominated and Bumble’s initiative to bring more women to festival stages has given me the greatest opportunity of my music career thus far – a performance slot at Lollapalooza. I’m excited to share my music and continue cultivating excellence and recognition amongst women!”
Not quite tired out just yet, fans were ready to get the party started on Sunday, wearing fun outfits and starting an impromptu breakdancing circle during LP Giobbi’s set at Perry’s stage in the early afternoon with the sun heating things up.
Musicians Chiiild and Sarah Barrios brought heart and soul to their performances at the Toyota Music Den and the BMI stages, adding their own flare and style to their songs.
There were so many activities to do at Lolla besides just seeing music. Folks could try some local Chicago food like deep dish pizza or a Chicago style hotdog, make Kandi bracelets, cool off in an air-conditioned Chicago city bus, get a custom graffiti fanny pack bag, and hang out and play corn hole and other games under some shaded trees.
Hulu partnered with Lollapalooza to host a livestream of many of the sets all weekend long. One notable set was Princess Nokia, who worked the stage with her backup dancers and wore an outfit of music festival beads and bracelets while bubbles flew around the stage.
Mid-day sets that stole the show were Irish singer-songwriter Dermot Kennedy, who thanked the crowd numerous times for coming out to support him, and pop duo Surfaces, who played a new single for the first time live. Both drew huge crowds on the North side of the festival.
Rap music also had steller representation on Sunday, with rap group Brockhampton performing their hits, along with Rico Nasty, G Herbo and late-announced headliner Young Thug, who replaced Dababy on the Bud Light Seltzer stage.
To close another spectacular long weekend of music was DJ Yellow Claw, musician Big Wild at the Grubhub Stage, EDM artist Alison Wonderland at Perry’s, and Foo Fighters wrapped everything up with a bang.
Lollapalooza is an intersection of music and fashion and culture. It’s a space where folks can come together to share ideas, express themselves, and feel in community together. It’s a place to dance, learn, meet new people and be whoever you want to be, which is why it’s so important that there is a space like this for young people.
Princess Nokia brought her indigenous roots into her music and dance performance. Chiiild discussed how it’s the artist’s job to write about current events and their take on what’s happening in the world. Miley Cyrus encouraged everyone to just be themselves, no matter how weird. It was invigorating, and felt like an exhale after this past year. Lolla delivered with not only an insane lineup, but with creating a community over these past four days. Live music is finally back with a bang, and Lollapalooza was the best place to do it.
