Tyler, the Creator, by Dan DeSlover

After a strong start on Thursday, day 2 of Lollapalooza on Friday brought about much cooler temps and headlining sets from the likes of Tyler, the Creator and Marshmello.

As evidence of the excitement from fans, it was hard to miss the influx of people carrying yellow shopping bags printed with "GOLF," proof of the number of purchases from the Lolla pop-up shop for Tyler's clothing brand Golf Wang, while there were also plenty of Marshmello headpieces across Grant Park.

Despite the great news Thursday of a more-than-90% vaccination rate among attendees, the shadow of Covid-19 still loomed on Friday. Memes of the massive crowd at Miley Cyrus' headlining set the night before created fodder on Twitter, and shortly after the city issued an indoor mask advisory, the festival responded by posting signs in shared indoor (and semi-enclosed) spaces—including in the media work tent—requiring facial coverings. 

Sadly, no matter the quality of the lineup, the story of Lollapalooza and Covid-19 are intertwined this year. But Friday was also proof of the determination of a city itching to get back to live shows, hanging out with friends, and spending time together, even if it's not exactly six feet apart.

The day began with a sunny performance from Gus Dapperton, who opened with a polished set on the T-Mobile stage. 

Over on the opposite end of the park, Mick Jenkins gave an incredible set on the Bud Light Seltzer stage, while Jacob Banks delivered a riveting, absolutely moving performance on the Lake Shore stage.

LOLLA 2021: Day 1

Mid-afternoon, it was Jordan Benjamin (aka grandson) who stole the show, offering up one of our favorite performances of the weekend, giving the crowd at Grant Park an intense Rage Against the Machine vibe as he charted through a slate of fan favorites, joined by Chicago's own Vic Mensa on his song "Oh No!!!" and Jessie Reyez near the end of the set for a live debut of their new collaboration "Rain," from the new Suicide Squad soundtrack.

Next up was Cam at Tito's Handmade Vodka stage, where the singer more than proved herself a good fit for the eclectic Lolla lineup. As the unofficial flag bearer for the country genre among this year's mostly pop and hip-hop roster, Cam made herself at home and delighted the crowd with a sunny performance. She later admitted she needed the experience of being back on stage and performing with live fans perhaps just as much as they needed to be there spectating. 

On the Grubhub stage, tucked in between the shade of the trees, the elusive Emotional Oranges were front and center, drawing heavily on 90's music influence with their performance and their backup dancers. The rising duo has been one to watch, and with this standout performance, they proved exactly why that continues to be true.

Both Polo G and Roddy Ricch also gave massive performances, with the latter paying tribute to the late Pop Smoke, whose song "The Woo" features 50 Cent alongside Ricch.

As the sun began going down and the temperature dropped, it was Lauv who attracted an incredible crowd at the Bud Light Seltzer stage. After making a few slight stumbles, he candidly told the crowd he was out of practice given the last year and a half of being stuck at home. Even as he regained his composure, he never lost the crowd, keeping everyone safely in the palm of his hand the entire time, all the way until his finale "I Like Me Better," which required fans' help to overpower the music coming from nearby Tito's stage.

By the end of his set, he was clearly emotional, sweaty and, as he previously established, grateful to be back performing in front of so many people. It was a welcome reminder of how, despite his incredible success, Lauv remains earnest and vulnerable. And it's part of why so many people connect with him and support him.

Jack Harlow, who has become one of this year's big breakout stars, was a hit across the park at the Lake Shore stage. As the perfect lead-in to Tyler's performance at next-door T-Mobile stage, Harlow gave full energy and the crowd was enjoying every second of it. He even came down to the pit to greet many of them as they cheered excitedly.

When nightfall arrived, Omar Apollo appeared as a silhouette at the center of the Grubhub stage. Surrounded by moody lighting, the singer, whose talent is simply undeniable, entranced the crowd, and made a case for himself as a future headliner of the fest. Sure, that's been said of artists before, but Apollo is special. He is in a different tier, and it wouldn't be surprising at all to see him top-lining future editions of Lolla.

That brings us to the night's actual headliner, Tyler, the Creator. While the artist born as Tyler Gregory Okonma previously proved his worthiness in the conversation of great artists with his LP Igor, which was Variance's Best Album of 2019, his Lolla set should put to rest any question of his stature as a performer—and certainly his merit as a headliner.

Leading into this year's Lollapalooza, of all the four core headliners (Miley Cyrus, Post Malone and Foo Fighters being the others), Tyler's standing was perhaps the most questionable. He's not a Top 40 artist with big radio hits like Miley and Posty, and he's not a legacy act like Foo Fighters, who are already longtime Lolla favorites.

But Tyler made clear he had every right to be closing out day 2 of the fest. Every right to be on the main stage. And every right not just to be considered a great music-maker but a great live performer, someone who didn't come to just jump around for 90 minutes but instead to deliver a thoughtful, well-crafted presentation. Beginning with his entrance as a bellhop to his changing stagecraft throughout, his lighthearted chatter between songs, his riveting song delivery and his attention to small details, it was clear we were watching a more mature Tyler. An artist who was coming into their own.

The artist we saw on Thursday night was a true visionary, a visual and creative master whose name belongs alongside such contemporary greats as Kendrick Lamar, Beyoncé and Kanye West. 

See photos from Lolla day 2 below.

Emotional Oranges, by Sydney Gawlik
Jack Harlow, by Ashley Osborn
Lauv, by Roger Ho
Mick Jenkins, by Pooneh Ghana
Omar Apollo, by Miranda McDonald
Omar Apollo, by Miranda McDonald
Lollapalooza 2021, by Dan DeSlover
Lollapalooza 2021, by Dan DeSlover
Jack Harlow, by Dan DeSlover
Lollapalooza 2021, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
Gus Dapperton, by Dan DeSlover
grandson, by Dan DeSlover
grandson, by Dan DeSlover
Jacob Banks, by Dan DeSlover
Jacob Banks, by Dan DeSlover
Cam, by Dan DeSlover
Polo G, by Dan DeSlover
Roddy Ricch, by Dan DeSlover
Roddy Ricch, by Dan DeSlover
Jack Harlow, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
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Emotional Oranges, by Sydney Gawlik
Jack Harlow, by Ashley Osborn
Lauv, by Roger Ho
Mick Jenkins, by Pooneh Ghana
Omar Apollo, by Miranda McDonald
Omar Apollo, by Miranda McDonald
Lollapalooza 2021, by Dan DeSlover
Lollapalooza 2021, by Dan DeSlover
Jack Harlow, by Dan DeSlover
Lollapalooza 2021, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
Gus Dapperton, by Dan DeSlover
grandson, by Dan DeSlover
grandson, by Dan DeSlover
Jacob Banks, by Dan DeSlover
Jacob Banks, by Dan DeSlover
Cam, by Dan DeSlover
Polo G, by Dan DeSlover
Roddy Ricch, by Dan DeSlover
Roddy Ricch, by Dan DeSlover
Jack Harlow, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
Tyler, the Creator, by Dan DeSlover
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