Lollapalooza 2021 Day 2 Recap: Tyler, the Creator Led a Great Day for Hip-Hop

With additional performances by Mick Jenkins, Kenny Mason, AG Club and Jack Harlow

lollapalooza 21 tyler the creator 2021 day 2 recap
Tyler, the Creator, photo by Jen Vesp

    Day 1 of Lollapalooza 2021 was a reminder that if we ever get the COVID-19 crisis under control, a climate crisis is lurking. But the oppressive heat of Thursday gave way to a wonderfully temperate Friday, as Chicago’s not-so-secret luxury, the lake effect, reasserted its dominance. Like Paris in springtime or New York in the fall, summertime Chi remains one of the great urban wonders of the world.

    The perfectly cool weather found its complement in an even cooler collection of beats. The discriminating ear of Tyler, the Creator led to a staggeringly fun set, Mick Jenkins made a powerful statement, while Kenny Mason, AG Club, and Jack Harlow explored different avenues of the same genre. Check out some of the highlights from a great day for hip-hop below.

    — Wren Graves

    Editor’s Note: Check out our full Lollapalooza performance photo gallery by Jen Vesp, as well as our backstage artist portrait gallery from Shervin Lainez.

    Rookie Brought It Back to ’06


    While old-school Lollapalooza fans sometimes find the festival’s modern incarnation hard to recognize, there are still honest-to-God rock acts lurking between the schedule’s abundance of pop, hip-hop, and EDM. Armed with gnarly guitar solos, a chugging rhythm section, and an organ player with a cigarette planted firmly between his lips, Chicago six-piece Rookie bashed out a set of sentimental bar rock (including highlights “Hold On Tight” and “I Can’t Have You But I Want You”) that called back to the days when bands like the Hold Steady and the Black Keys still roamed Grant Park. If you brought your dad with you to the fest today, I hope he found these guys. — Tyler Clark

    Gus Dapperton Prioritized Energy

    Dapperton sacrificed enunciation for energy, marching in place and punctuating his phrases with exuberant howls. While his lyrics weren’t easy to understand, he made up for it with a playful personal presentation: a baseball hat, face piercings, and the traditional tie, vest, and skirt of a catholic schoolgirl uniform. If that didn’t bring a smile to your face, the chemistry among the band members would do the trick. Every single person on stage spent their free moments dancing. — Wren Graves

    Kenny Mason Turned the Woods into a Mosh Pit

    lollapalooza 2021 kenny mason day 2 recap

    Kenny Mason, photo by Jen Vesp


    The BMI stage is nestled into a little copse of trees in a quiet corner of Grant Park. Well, usually it’s quiet, but on Friday it hosted perhaps the first earthquake in Chicago’s history. Mason masterfully conducted the crowd, encouraging them to get low, jump, shout the word, “free,” and above all, to make some noise. With a set heavy on cuts from his 2020 LP Angelic Hoodrat, the rapper kept stealing audience members from nearby stages, so that his crowd more than doubled from beginning to end. — Wren Graves

    Mick Jenkins Walked on Clouds

    Jenkins performance saw more smoke coming from the crowd than the fog machines on stage. “Who smoking?” he asked. “Last time I did Lolla, weed wasn’t legal, now it’s legal, so what y’all smoking?” You wouldn’t think he smoked himself from his breath control. Without a hype man or prominent backing track, he commanded the headline stage, while also connecting with the audience on the mental toll that Covid had taken. Before his song “Spread love” he said, “Spread more love and less germs.” He made space for his Free Nation artist Stock_Marley to play two new songs, and also debuted some fresh tracks of his own: “Contest,” and the tour-de-force, “Things You Could Die for if Doing While Black,” which accounted for perhaps the best single-song performances of the fest to date.. — Wren Graves

    Of Course Cam Will Play That

    Country singer Cam got into the festival spirit with an orange see-through slip and a golden circlet of stars. She opened with “Diane,” and soon the insistent requests from the crowd elicited a response. “Well, of course I’m going to play ‘Burning House,'” she said. “It’d be crazy to come to Lollapalooza and not play it.” She also honored calls for “Classic,” “Changes,” and “Til There’s Nothing Left,” and tore through a cover of The Cranberries “Zombie.” The performances took place as her daughter looked on, and if anyone was confused on the mechanics of child creation, she also riffed on the birds and bees. — Wren Graves and Tyler Clark

    Giveon’s Mom Was Watching


    A guest spot on Drake’s 2020 song “Chicago Freestyle,” has led to one of the biggest Chicago venues: R&B singer Giveon has had quite a year. His set at the massive T-Mobile stage was the kind of spot normally reserved for veterans, but as he admitted, “This is my very first festival.” If he had any nerves, he didn’t show them, though he expressed some bewilderment at his rapid rise, and his set ended 15 minutes early due to a lack of material. At one point he called to, “Cut that shit,” and invited the crowd to sing some “Oohs,” a capella. “Please,” he urged them, “my mom is watching.” The audience did mom proud. His blockbuster single “Peaches” soundtracked the the last rays of daylight before the sun fell behind the Chicago skyline. — Wren Graves

    Polo G’s Hometown Show Was More Fizzle Than Sizzle

    lollapalooza 2021 polo g day 2 recap

    Polo G, photo by Jen Vesp

    Polo G’s third album Hall of Fame debuted at No. 1 on the Billboard charts last month, which set up today’s appearance at Lollapalooza as a victory lap for the Chicago rapper. Despite those auspicious circumstances, his set on the Bud Light stage felt like it was building to a payoff that never quite came. Maybe it was the cloudy weather, or maybe everyone in the crowd was just saving their energy for Tyler, the Creator, but even the appearance of No. 1 single “Rapstar” failed to sustain the kind of energy everyone was hoping for. Perhaps Polo G felt it too; he bounced with 10 minutes left on the clock, leaving his DJ to vamp away the rest of the set. — Tyler Clark

    White Reaper Might Slow Down But Never Stop


    The Louisville rockers didn’t really pause between songs, preferring to keep the pace set to ‘blistering.’ They dropped their major label debut, You Deserve Love, just months before the pandemic, and they seemed eager to make up for lost touring time. But after each track finished, they did take a slight rest in the form of short interludes ranging from bizarre anti-humor to reality-tv-style bits. One brief pause was explained by lead singer Tony Esposito as a “tummy ache,” and in others he said, “How’s the weather?” or pointed out that someone had lost their phone. He also said he’d been “looking at our DMs and there’s someone who needs our help,” then asked if there was a Valerie in the crowd. There was, and he informed her that an ex-boyfriend had been in touch to say he wanted her back, but that the dude sounded toxic and she should stay far away. “Might Be Right” got the biggest reaction. — Wren Graves

    Boy Pablo Went It Alone

    For most artists, no band means no show. Fortunately, someone neglected to tell that to Nicolas Munoz of Boy Pablo. With his entire backing band held up by visa issues, Munoz forged ahead solo, delivering karaoke-style renditions of his bedroom Scandi-pop favorites like “Dance, Baby!” and “Feeling Lonely.” The crowd stayed with him throughout, perhaps helped by Munoz’s self-deprecating humor. “Yesterday I had an afterparty show,” he said of playing solo, “and I was nervous I was going to poop my pants.” — Tyler Clark

    Roddy Ricch Got By with a Little Help from Polo G and DJ Mustard

    The T-Mobile set on the south end of Grant Park is a whale of a space, and Roddy Ricch almost got swallowed whole. You could see it starting after he had paced the great length of the stage for the fourth or fifth time. He began dropping the ends off his phrases, his energetic dancing turned into desperate wiggles, and whole couplets were replaced with, “Yeah! Yeah!” But after Polo G emerged to play their duet “Fame and Riches,” and DJ Mustard held down some bars on “Ballin,'” Ricch caught his breath. Energized by these visits with his friends, he rallied for a stronger second half, highlighted by the Pop Smoke collab “The Woo,” and a strong closing featuring “Rock Star” (presented without DaBaby or comment) and “The Box.” — Wren Graves

    AG Club Had the Best Set No One Saw


    While most of the festival decided between the viral hits of Jack Harlow and the id-first EDM of the regrettably named Brownies & Lemonade All Stars, real heads gathered under the trees at Grubhub for one of the weekend’s most underrated sets. Although AG Club drew a surprisingly small crowd, the Bay Area hip-hop collective rewarded those in attendance with a kinetic 45 minutes, firing off songs like “COLUMBIA” and “Memphis” with a brash confidence that would give Brockhampton a run for their money. When these guys come back to a bigger stage in a year or two, you’re gonna wish you’d been here.

    — Tyler Clark

    Jack Harlow Is a Marquee Idol

    lollapalooza 2021 jack harlow day 2 recap

    Jack Harlow, photo by Jen Vesp

    “This one is specifically for the girls,” Harlow said, and as the beat dropped for “Love Is Dro,” the girls responded with force. This handsome 23-year-old is a fairly conventional party rapper, but he oozes charisma, and was perfectly ready when Lil Nas X thrust him into a brighter spotlight with the new single “Industry Baby.” That track got one of the biggest reactions of the set, even if Nas himself didn’t show. But while a lot of the fans may be new, solo bangers like “Face of My City,” and “Sundown,” left the crowd vibrating. At one point he took his button-down shirt off to reveal a sleeveless tank top, and you should have heard the noise. “Y’all got anything left in the tank?” he asked. After “Already Best Friends,” he waded into the audience and instantly regretted it. “Woah, don’t pull me. Don’t pull me. You were right,” he said to a colleague, “Let’s get the fuck out of here.” That awkwardness aside, closing track “What’s Poppin” brought the house down. — Wren Graves

    Marshmello Brought Out the Kids


    I’ve been attending Lollapalooza since 2005. In those 16 years, I can honestly say that I’ve never seen as many kids under the age of 12 at the festival as I did at tonight’s headlining set from Philadelphia DJ and human cartoon character Marshmello. There were plenty of kids at heart there, too, ping-ponging along with the set’s strobing lights, bursts of fireworks, and attention-span-frying bursts of EDM. As for me? I’m 37, which means I tapped out after 20 minutes and went to lie down in a cool, dark place. To paraphrase a late, great philosopher: Lollapalooza is for the children.

    — Tyler Clark

    Tyler, the Creator Transformed

    lollapalooza 21 tyler the creator 2021 day 2 recap

    Tyler, the Creator, photo by Jen Vesp

    Tyler, the Creator emerged dressed as a bellhop and wheeling a luggage cart. He opened one suitcase, and performed a costume change before the first beat dropped. It was a promise: expect transformation.


    Some of the biggest set pieces were reserved for the beginning. He performed on a wildly rocking boat for the CALL ME IF YOU GET LOST tracks “LEMONHEAD,” and “WUSYANAME,” and floated high above the stage on a cloud for “SWEET.” He also told the origin story for one of the best rap songs of the year. On a road trip, “We drove to Utah, went to Starbucks,” and a white lady asked, “What kind of car is that?” But her tone was more, as he put it, “N—- you ain’t supposed to have that car. So I told her,” and here the beat for “LUMBERJACK” came thundering down as Tyler rapped, “Rolls-Royce pull up, black boy hop out!”

    He performed a suite of songs from Flower Boy, which he said, “Came after my ugly phase. But 19, 20, I was cute though.” This allowed a segue to his earlier works, including “Yonkers,” the music video for which famously showed him eating a roach. This man scarfed down a bug to get the opportunity to someday play for so many fans, and now that the time is here, he did not let it go to waste.

    One of the most thrilling sections came towards the end, when he donned the suit and bob-cut wig of his IGOR era. “I THINK” transitioned into “EARFQUAKE,” and a performance in front of a waterfall of sparks trailed off into a stark emptiness and an a cappella ending. His voice through the speakers was drowned out by the crowd. That was true no matter what form his shape-shifting performance took; any time he wanted, he could pass the mic to the audience and bask in the roar.


    — Wren Graves