Thousands of music fans descended on Grant Park Thursday for the first day of Chicago’s biggest music festival, Lollapalooza.
Festival organizers billed this year’s iteration of the four-day festival as the 20th anniversary, pointing to its Grant Park debut in 2005 — although it opted for a virtual version during the COVID-19 pandemic in 2020.
With big-name acts like hip-hop superstar Megan Thee Stallion and Irish rock darling Hozier topping the bill, perhaps the most anticipated set of the day was the Midwest’s own pop star, Chappell Roan.
Throngs of fans in bedazzled, bubblegum pink cowboy hats anxiously crowded the barricades of the festival’s main stage, some waiting more than five hours for Roan’s set. Elsewhere across the festival grounds, Roan fans could be spotted wearing pink, camo caps reading “Midwest Princess” and sporting makeup and elaborate outfits resembling her music video looks.
One notable difference in this year’s festival was the amount of sponsored pop-ups throughout the festival area. Fans could roller skate near Buckingham Fountain as part of a Coca-Cola promotion, decorate a pair socks at the “GOLDTOE Sock Creation Station” and sing at the “Jack Daniel's Music & Karaoke Experience.”
Promos aside, the music was still the main focus, with midday sets from artists like Dallas rapper BigXThaPlug and Tyla drawing crowds of energized fans.
It all took place under a cloudy sky early on that threatened to rain on festivalgoers. But after a few drizzles, the clouds finally parted and sunshine emerged on an afternoon that was hot and humid, as plenty of festival goers laid out in the shade and populated constant lines at hydration stations. — Matt Moore
Matt Hansen asked the question on everyone’s mind Thursday at the kickoff of Lollapalooza: “Is anyone psyched to see Chappell Roan today?”
If it wasn’t clear by the rhinestone pink cowboy hats, “stan” t-shirts and other summer brat wear, the applause made the answer unanimous. Like the rest of the crowd, Hansen came off like a giddy fan, not just for the woman of the day, but also just for being at Grant Park.
“I never expected this many people to turn out. … This is so crazy,” the 22-year-old shared regarding the crowd for his early-bird 1 p.m. set time.
It should’ve come as no surprise, though. The TikTok generation has been well aware of his incredible songwriting chops and emotional delivery (spanning an octave or two) behind a range of covers and original songs like “Let Em Go” and his gate crasher “Something To Remember” that have quickly gone viral. Hansen has 2.5 million followers on TikTok alone.
It might seem obvious to draw comparisons to Ed Sheeran (another guy with a mop of red hair, sometimes playing acoustic and offer commanding ballads), but Hansen fits the bill in more ways than one, with a bit of Coldplay, Lewis Capaldi and even the night's headliner Hozier thrown in the mix.
There’s an incredibly intimate sense of urgency to Hansen’s music and an emotional maturity to songs like “Lifejacket” and “Versions of Forever,” either of which would could fit in the next Nicholas Sparks film. Playing “Better Off Without Me,” Hansen shared it was his first song to “make me realize my music could mean something to people.” And it was evidenced by the video screens that frequently cut to images of fans, eyes closed, singing along to every word.
The songwriter, joined by a drummer and guitarist/keyboardist, was short on the covers that first catapulted him, solely choosing a deeply heartfelt cover of Goo Goo Dolls’ “Iris” to a huge reaction. He prefaced it, sharing with any musicians in the crowd, “Post covers, that’s how people find you, and then give them your originals. It might lead you to play a stage like this, it’s pretty surreal." — Selena Fragassi
“I’m here to show you why everything is bigger in Texas,” BigXthaPlug shared with the super hyped crowd that had gathered to let loose at his mid-afternoon set.
The Dallas rapper’s nom de plume is fitting for his stature (he once had dreams of playing in the NFL), but also his larger-than-life presence as a skilled rapper and emcee. Born Xavier Landum, the 26-year-old has only been on the scene since 2020, when he self-released his first collection of tracks, “Bacc from the Dead.”
But he’s already gained a reputation as quite the draw, as seen at his Lollapalooza debut as well as recent collaborations including Shaboozey’s "Drink Don't Need No Mix.” BigX hints at his fortuitous rise in songs like the uber hit “Mmhmm” in which he talks about starting to rap and “six months later, I’m rich.”
Several times over the course of the hour, he and his four-man posse applauded the Chicago crowd on bringing the energy and opening up several pits. BigX also asked fans to “stop throwing s- - - on stage” early on, his deep drawl coming through, as some of the boxed water that security had handed out to help fans battling the day’s heat was tossed around instead.
Initially starting the set wearing a Deion Sanders No. 21 shirt, the rapper quickly doffed it as the sun finally came through the day’s cloudy overhang, exposing his chest full of tattoos and the gold chains around his neck like he has been collecting them for this very moment.
Even with the energy his set brought, ultimately it was hard to compete with Chappell Roan’s set time looming and swaths of people departing halfway in to stake their spot at the adjacent T-Mobile Stage. Perhaps seeing the migration, the rapper got in a plug for a tour that will bring him back to Chicago at Avondale Hall on Nov. 16. “I wanna see all your faces there,” he warned, though his performance sold it enough. — Selena Fragassi
Although she’s a global pop sensation in her own right, it appeared at first that Tyla may have had her work cut out for her before she began her set Thursday — winning over a massive sea of sweaty Chappell Roan fans waiting for their star’s 5 p.m. set, wilting under bright pink cowboy hats.
The South African artist soon went to work, delivering her blend of R&B, pop and amapiano while a team of six dancers joined her with air-tight choreography.
A large blow-up tiger sat center stage, a nod to the singer’s home country and her fans, whom she refers to as “Tygas.” At various points throughout her set, Tyla would sing while perching on a platform just behind the tiger, appearing to ride it.
Songs like “Safer,” “No. 1” and “Truth or Dare” kept the crowd moving as she glided through just about every track off her self-titled debut album from early spring, a breezy record that marries meditative deep house beats and sunny afrobeats production with catchy pop and R&B hooks.
Another highlight came when she told the crowd, “I got something special for you,” as the beginning bars of Aaliyah’s classic hit, “Rock the Boat” played and Tyla performed a rework of her song “On and On.”
It was almost as if Tyla brought the sun with her, as the clouds that hung over Lollapalooza all day began to part the further she moved through her set, heating up the crowd.
Dancing ceaselessly and singing along to each song, the many Tyla fans present made themselves known among the “Pink Pony Club” contingent.
At one point, she asked “Anyone from South Africa?” prompting modest whoops overall, but passionate yells from a few clusters of fans waving South African flags fervently.
It’s been a whirlwind year for Tyla. Since the release of her breakthrough single, “Water” in July 2023, the 22-year-old has been catapulted into fame, topping charts in multiple countries and netting a Grammy Award.
An international tour had been on the books for this year, but the singer said in March that she had been “silently suffering with an injury” and had to cancel the majority of her dates, making Thursday’s Lollapalooza set one of her first main stage performances this year.
If there were any cobwebs during her set Thursday, it was hard to tell, as she gave a strong, albeit mellow, performance accented by fun dance breaks.
The set neared its crescendo toward the end, when she kicked into the album stand-out “Jump,” with many in the crowd rolling their hips as Tyla and her dancers did the same.
By the time the beginning bars of her hit, “Water,” poured out of the main stage’s speakers, the crowd broke out in screams as thousands held up their phones to film.
“I wonder what song this is?” she asked with a mischievous smile, before leading fans in a singalong of the song’s hooky chorus. Once the beat dropped, festivalgoers grooved along as she moved into the verses. At one point, she passed her mic to security, who held it up for a fan to do their best attempt at the chorus. Tyla took out her in-ear monitor to hear the thousands of voices singing her song back to her.
She then capped the song with one final dance break, as one dancer grabbed the mic to emcee while Tyla broke it down on the stage before leaving the roaring crowd. — Matt Moore
Kesha’s set on Thursday started with a word appearing in large text on the IHG Hotels & Resorts Stage screen: “Freedom.”
For the next hour, the pop star gleefully showed a packed crowd what freedom means to her — and it involves singing in a nun’s habit, backup dancers in cat mascot masks, a four-piece marching band and full autonomy to do whatever she wants.
It was a heartfelt, campy, joyous, fever-dream of a spectacle that was both a celebration of the zaniness we’ve come to expect from this seasoned performer — and a reintroduction to an artist now 15 years into her career.
The crowd went wild from the moment she started her 2010 hit “Tik Tok,” which featured her a revised opening line — “Wake up in the morning yelling, f- - - P-Diddy” — as the words appeared on the screen behind her.
In addition to her dancers, Kesha was joined onstage by a drummer and a multiinstrumentalist hopping from guitar, bass and synths. The two-piece anchored a career-spanning setlist and added electricity to an already high-energy performance.
A slightly unsettling moment happened early, when she performed “Cannibal,” clutching a replica of a heart while her dancers covered themselves in fake blood, which stayed on them for a majority of the set. But the devout fans singing and dancing along ate it up.
And when she commanded her audience to “give me all your clothes!” during “Take It Off,” many obeyed, throwing articles of clothing onstage.
Another crowd pleaser was “Timber,” her 2012 collaboration with Pitbull, which she performed after one of several costume changes. Her dancers took off their shirts and donned cowboy hats.
Her early hit “Your Love is My Drug” was given a fresh rework into a fast, rock-leaning power pop anthem, which saw her strumming a hollow-body guitar on the chorus while phalic drawings cycled on the screen behind her.
The set also saw the live debut of “JOYRIDE,” a clubby, high-octane track she dropped last month — her first release as an independent artist on her own label, Kesha Records. Kesha performed the song with an exuberance and lightness.
Kesha made her Lollapalooza debut back in 2009, and soon rose to ubiquity with a slurred, talk-sing, life-of-the-party persona that skyrocketed her to the top of the charts. In the years since, the 37-year-old has been open about intense struggles with mental health, abuse and record label battles.
On Thursday, she reflected on her career and that inaugural Lollapalooza appearance.
“It was the first time more than five people came to see me play — I remember I was so f - - - ing terrified that I would be judged,” she said, explaining that throughout her career she has faced a cruel and constant amount of criticism.
“But now, standing here as the woman I am right now, I can see that all of that hate has made me into one powerful f - - - ing mother f- - - - -,” she proclaimed to loud cheers.
Another acknowledgment of her past hardships came during her 2017 single “Pray.” People in the crowd belted along with her, some appearing emotional, making for one of the set’s biggest moments.
“That song has a whole different meaning to me now,” she said. “Thank you for standing by through the hardest f - - - ing time in my life.”
Fueled by the fire expressed in her song "Woman,” off her 2017 album “Rainbow,” Kesha asked: “Did y’all hear that this country being run by childless cat ladies? Can someone tell that motherf - - - - - J.D. Vance that he’s correct and that it feels so f - - -ing good!
“I’m so happy right now — the only thing I miss is my kitties,” Kesha said. “Can someone bring out my pussies?” Cue her dancers crawling on stage wearing stuffed cat heads, clawing and cleaning themselves like an off-off-off Broadway burlesque version of “Cats.” The crowd was practically feral.
This was followed up by a clip of Kamala Harris’ now viral moment, “You think you just fell out of a coconut tree?” that gave way to another classic Kesha track, “Blow.” A four-piece drum line walked out for this one, adding a circus-like feel.
Thursday’s performance came just as Chappell Roan wrapped her highly anticipated set on the main stage, where Kesha was initially supposed to perform. Originally booking Roan for a smaller stage, Lollapalooza organizers reportedly took note of her fast rise this year and requested a swap from Kesha, and she graciously agreed.
But make no mistake, having Kesha’s larger-than-life persona on a smaller stage — and forcing fans to squeeze in front of it — felt like a bit of a misstep. It was a solid performance fit for the main stage.
The set ended with another early-career single 2010’s “We R Who We R.”
On Thursday, Kesha imbued the song with a new sense of urgency, as her dancers waved Pride flags and four drag performers joined her onstage.
“Support local drag!” she yelled before thanking everyone and walking off the stage. —Matt Moore
Check back later for more reviews.
For anyone emerging from sea of people that was the Chappelle Roan set (including this reviewer), getting to the other side of Grant Park to catch adan diaz at the BMI Stage was a challenge. But the last half of the singer-songwriter-guitarist’s set was well worth the trek.
The Chicago area native and DePaul student headlined the rising-star stage for Day 1 of the festival like a well-oiled musician, even if the booking came as a surprise to him. The 19-year-old told WBEZ he was only in attendance at the event once before, and just for a few hours, to catch pals The Linda Lindas last year.
But clearly Diaz took cues from the young punk rockers, bringing a similar level of youthful passion and physical bounce to his performance. Even when one of his guitar strings broke, Diaz took it in stride, strumming away his pop-rock love odes with extra intention.
Later, he took a risk by performing an unreleased, unfinished song, “Run It All Back,” towards the end of his 40-minute set, though admitting he was hesitant to do so. Thankfully, his band (featuring an extra guitarist, bassist and drummer) encouraged him to use the platform to test it out. With even more polish, it’ll be another standout for the troubadour, who’s made a modest ruckus since his “Legroom” EP was released in 2021, when Diaz was barely old enough to drive, and also around the time he debuted on stage at Lincoln Hall.
One of the standout offerings from the EP came when the Mexican American talent offered up “Dificil,” a song with bilingual lyrics. Several in the crowd piped up for the number, cheering at the Spanish parts and digging out their phones to take video. It’s edification of how much representation matters, and thankfully Lolla keeps heeding the call. —Selena Fragassi
Check back later for more reviews.
Notices of potentially severe weather were arriving from Lollapalooza's social media accounts Thursday night as English singer, rapper and producer Labrinth prepared to take to the T-Mobile main stage.
But ultimately, the clouds looked more menacing than they acted, with only drizzle falling momentarily as Labrinth took to the stage for an impressive, uninterrupted set.
“What the f- - - is this, y’all? Oh my …” mused the rapper, clearly moved by the substantial crowd gathered for the performance on Grant Park’s south end. “I thought people didn’t know me in the States. I wanna say this and mark it down for yourselves: Thank you for making this the best day ever!”
Luckily, the thunder sound effects interspersed between songs throughout the set acted only in an ironic fashion as Labrinth got going with “Formula.”
Labrinth’s was a rap set where delicate moments featuring often nuanced and layered harmonies could stop on a dime, veering off in wild but exciting directions ranging anywhere from strings to crushing bass drops throughout a performance which saw Labrinth backed by live drums and backing vocalists on a multi-tiered stage.
“We got some singers out there! Yeah, come and sing with me!” said Labrinth excitedly, setting up “Still Don’t Know my Name,” a track which appeared in the HBO drama “Euphoria,” for which Labrinth has scored both seasons. “This was my second hit and it brought me to the U.S. I always like to play it and remind myself where I come from,” he said, strapping on a guitar for a scorching live solo.
Lush harmonies drove the early moments of “I’m Tired,” a collaboration with “Euphoria” star Zendaya. During the performance, Labrinth acted more than he danced, taking a theatrical approach which lent a cinematic feel to the performance and song, placing his left hand over his heart while crouching down on stage, piano sparkling throughout.
“I live for everything I do,” said Labrinth on stage at Lollapalooza. “I live for what I write. If you have a passion for what I do, thank you.” —Jim Ryan
