The baseball fields in Grant Park on the first day of Lollapalooza Credit: Kathleen Hinkel

For longtime Chicagoans, especially those who go to a lot of festivals, Lollapalooza has clearly lost some of its magic. People definitely had some reservations going into this year. As recently as 2017, four-day Lolla passes would sell out within two or three hours of dropping online. Last year, they didn’t sell out for eight days—and in 2019, they were still available the week of the fest, which is unheard of.

Those slower sales no doubt had something to do with the hefty price of a four-day pass: $340 plus sky-high fees. Add that to the fact that Lolla took place two months into a summer fest schedule that’s been even more packed than usual, and it looks likely that festival fatigue is affecting even the biggest event of the season. Speaking for myself, I feel like the crowd’s median age has skewed further toward “first high school dance” since I attended my first Lolla as one of those high schoolers in 2012—and that’s been enough to give me pause every year.

As usual, festivalgoers had to deal with cheap-jersey-wearing suburban teens who visit Chicago once per year, and with security staff who seemed oddly selective—on Friday a video of dozens of fence jumpers went viral, largely because it ended with an officer stopping a lone kid with a prosthetic leg. Despite all that, though, Lolla was solid, and the music provided plenty of highlights.

Day one

Given my taste, day one of Lolla had the least eyebrow-raising lineup. The few bright spots included hometown hero Saba, who performed songs from Bucket List Project and Care for Me with infectious energy in front of a graphic of a glowing CTA train pulling into a Loop station. He brought out Saint Louis native and longtime Chicago scene fixture Smino for a guest verse, calling him a “Chicago legend.”

Saba shared his infectious energy with Thursday’s crowd.Credit: Kathleen Hinkel
Lil Baby’s crowd was so large that people climbed nearby trees to get better views of the stage.Credit: Kathleen Hinkel

Later on the same stage, Lil Baby performed his many recent chart toppers. He drew a crowd so large that some fans climbed trees by the stage to get better views—and whether they knew it or not, they ended up entertaining Snapchat story watchers in several time zones.

Calboy brought a personal touch to the American Eagle stage.Credit: Kathleen Hinkel

Day two

Day two was my personal favorite, and the excitement started early. Local rapper Calboy drew impressive energy for a 12:50 PM set, but while his smash hit “Envy Me” will surely be remembered as a legendary Chicago rap song, much of the crowd seemed unfamiliar with the rest of his music—few people sang along to the deeper cuts, and Calboy had to use audience prompts such as “Put your hands up!” to keep everyone engaged.

Calboy brought out Chicago sweetheart Chance the Rapper, who did a couple songs off his new album, The Big Day, and drew cheers when he climbed on a speaker and exclaimed that he’s from the “greatest city in the world!” The collaborative culture that has invigorated Chicago’s hip-hop scene was on full display, and Chance’s surprise entrance (not his last of the festival) ramped up the chaos of Calboy’s already energetic show. He closed his set by performing “Envy Me” twice in a row, much to the glee of the crowd. I don’t know what I expected, but fans moshing instead of doing the customary “wop” (a dance made famous by Calboy’s hit) was something I didn’t expect to see in this lifetime.

The intro to 21 Savage’s fiery set was a video montage of soundbites from past interviews and homages to close childhood friends whose violent deaths have shaped him. Another montage arrived midway through his performance, comprising news clips addressing his detention by ICE earlier this year. Though the videos clearly sent the powerful message that Savage had overcome long odds to reach such a big stage, the videos seemed disconnected from his performance—he didn’t offer much additional context from the mike. The crowd didn’t seem to mind, though: they jumped and rapped along as he shuffled through his hits, and then went wild when he brought out Childish Gambino, who for some reason was wearing a sling and a neck brace, to perform “Monster.” Savage certainly satisfied the moshers and the casual fans who were only there for the Top 40 hits, but I would’ve liked to see him weave more of the personal story illustrated by the sobering videos into his performance.

Tierra Whack very likely wore the only shirt at the festival that had its own hairstyle.Credit: Kathleen Hinkel

One of the funnest shows all weekend came from recently crowned XXL Freshman Tierra Whack, who repeatedly called the Lolla audience her “best crowd ever.” She was her full, eccentric self onstage, rocking a crew-neck emblazoned with a stylized cartoon of herself that had actual 3-D braids growing out of its head. She’s beloved for the bouncy, idiosyncratic “art raps” on Whack World, but she’d clearly come to Lollapalooza to make a statement: two songs in, she gave a matter-of-fact performance of the boastful “Gloria,” where she stakes her claim in the male-dominated rap industry and tells her competition to call her “Big Whack,” that made me literally run to grab my phone out of the T-Mobile charging station so I could record it.

Friday’s headliner was Childish Gambino, who put on a dazzling performance that was also (in a sense) the longest of the weekend. Because he’d apparently come straight out of the ICU to guest on 21 Savage’s 6 PM set, confusion had spread in the crowd about the status of his show later that night. However, once 9 PM hit, it became clear that we’d all been trolled or had just witnessed a legendary healing experience—he was back to the Gambino we’ve come to love, singing and gyrating throughout his soulful set and walking along crowd barriers to dance and take pictures with fans. Before beginning, he implored everyone in the crowd to put their phones away, explaining that this was “an experience” to be felt. Several times he asked the crowd, “Can you feel it?” The energy of his thousands of fans was so palpable, it was hard not to.

Day three

My Saturday began with Smino, whose set included an onstage marriage proposal and another guest appearance by Chance, who performed “Eternal,” an ode to marriage from The Big Day. Smino gives a lot of love to Chicago for shaping him as a creative, and he gets a lot back—among the lower-billed acts, he had one of the most engaged and participatory crowds.

Lil Wayne drew a throng that spilled out of the huge area on the south side of Grant Park reserved for the T-Mobile stage. He quickly shuffled through hits dating back to Tha Carter I, often just performing a hook before moving on to the next smash. For much of the show, I was alternating between fighting off drunk teens shoving to the front and processing an existential crisis after realizing that no one around me knew the words to “A Milli.” When I was growing up, not knowing that was like not knowing the first two lines of “Don’t Stop Believin’.” Is this what it’s like to feel old?

J Balvin won the day, however, delivering an electric performance as the first Latin-music headliner in Lollapalooza history. The Colombian-born star offered one of the most colorful sets of the weekend, down to his bright green dyed hair. He dedicated his performance to the reggaetoneros who paved the way for this moment of mainstream validation, cycling through classic reggaeton songs and hits from last year’s Vibras—and stunning the crowd by bringing out legendary Puerto Rican duo Wisin y Yandel for a surprise performance. Balvin’s celebratory show was punctuated by literal fireworks.

Fans at Masego’s set on SundayCredit: Kathleen Hinkel

Day four

Day four brought some great performances, beginning with J.I.D, who’s been having a hot 2019 thanks to his heavy involvement with Dreamville Records’ Revenge of the Dreamers III compilation album. J.I.D excited the crowd with his rapid-fire rhymes as he paced up and down the catwalk, which he said Lolla organizers had told him “was for Ariana” but which he definitely claimed as his own for the duration. Later he invited labelmates Earthgang and collaborator Smino onstage to perform “Sacrifices.”

Self-described “trap house jazz” artist Masego showcased his versatility, putting on a groovy show as he alternated between call-and-response chants with the crowd, playing saxophone, and improvising on keyboard—he even created a beat in real time using the keyboard and a drum machine, then sang along to it.

The front row of the Meek Mill crowdCredit: Kathleen Hinkel
Meek Mill had more than just his Lollapalooza set to celebrate.Credit: Kathleen Hinkel

Meek Mill drew the second-largest crowd of the day, and he had a big victory to celebrate: the 2008 conviction that had kept him either imprisoned or on probation ever since had finally been overturned. Meek threw a party for which he provided the soundtrack, mostly performing his hits from over the years. Much like 21 Savage, Meek chose to forgo unscripted thoughts about the recent news about his legal troubles, instead focusing on the chaos-inducing hits (such as “Dreams and Nightmares”) that helped make him a household name. He also brought out Calboy as a guest, and shouted out Chicago rapper Lil Durk onstage.

One of the not-to-be-missed performances of the weekend was the electric set from flamenco singer Rosalía. Dressed in lime green, she worked the crowd as much as any artist at Lolla, moving in precise sync with her backup dancers. The crowd grew as her performance went on, as many unsuspecting people making the trek to Meek Mill’s nearby stage stopped in their tracks to watch. It seemed Rosalía could hit any note she wanted, from a lullaby-like whisper to a powerful full crescendo, and her heavy use of a cappella adds enough drama to her music to make you feel like you’re listening to a score.

The verdict

As any festivalgoer can tell you, a lot goes into a successful weekend. This was the first Lollapalooza I’d attended in four years, and I took on the daunting challenge of tackling all four days alone. Still, all things considered, I enjoyed my time at Lolla this year. I saw some truly brilliant performances, complete with surprising guests, and there were good vibes all around. The festival provided plenty of entertainment to keep me busy between sets, and though the food was predictably way overpriced, it looked decent. Not to mention, we were blessed by Mother Nature: not a single lightning flash or storm gust even threatened to force an emergency evacuation of Grant Park, as happened on both of my last two Lolla trips.

Despite all this, something felt missing. It was us. That’s us meaning Chicago. For me, us means Black Chicagoans from the west side. As a lifelong Chicagoan, it’s hard not to see life in terms of its various intersections.

Lolla organizers have a lot of work to do to keep the event relevant as a main attraction for summertime Chicago. Though Lollapalooza began as a rock festival, one of its main draws today is its commitment to booking artists from a wide range of genres. There’s something for everyone, including the (preteen) kids—every year since the fest took root in Chicago in 2005, one of Grant Park’s smaller stages has hosted a Kidzapalooza mini fest.

The huge, engaged crowds drawn by hip-hop, R&B, and Latinx acts should be a clear sign to Lolla that more such artists would be welcome—but would the crowds grow along with the bookings, given that the Black and Brown Chicagoans who make up the core of these artists’ fan bases are largely priced out of the festival? The culture can’t be re-created onstage with just a special guest performance by a star from the city. That may fool the thousands of suburban teens pouring out of Metra trains and into Grant Park, but not us.

As I’ve mentioned, Lolla feels . . . disconnected from the culture. Especially Chicago culture. This sort of criticism—about being “touristy”—was also directed at ComplexCon Chicago last month. But 2019 was ComplexCon’s first year in the city; Lollapalooza has been here for 15. Some notable local acts did appear, and Chance had his guest spots. The fest even added rising north-side hip-hop star Polo G at the last minute due to a cancellation. But nonetheless Chicago feels underrepresented, aside from the unmistakable skyline that served as the backdrop for countless festival selfies shared on social media.

Slow ticket sales and a lukewarm reception across the city, despite a host of big bookings, should point to one thing: though Lolla is undoubtedly cool, it needs to regain the Chicago stamp to continue to thrive here. Organizers should stop focusing on getting bigger and worry about getting better. “Access” is the word of the weekend, and Lolla will continue to stray further from the hearts and minds of Chicagoans if it continues to keep so much of the culture out.  v