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Lollapalooza's Chicago Performers Proved Just How Vital the City's Music Is Right Now

Vic Mensa, Towkio, Joey Purp, Saba, Smino, and other Chicago artists connected the city's various threads and offered a strong argument that it has the most exciting rap scene anywhere.

Vic Mensa / Photos by Petya Shalamanova

There is always something to prove here. That much is certain after Lollapalooza weekend. Unlike artists from other cities, Chicago musicians must work twice as hard to get half as far as their coastal counterparts. They do not have the luxury of inborn scenes covered by massive media outlets. Chicago is structured through small blogs and a handful of newspapers and magazines. So local musicians must push themselves beyond the superficial limits of musical stardom. If they want to prove their worth on a national stage, they ultimately must show why their artistry matters. They have to present themselves to outsiders with an answer about what it means to be a part of this city.


It has been an important year in the development of Chicago artists. Musicians including Chance the Rapper, Towkio, Joey Purp, Vic Mensa, Saba, Sir the Baptist, and Smino released new music within the past 12 months. And each performed at the festival in some capacity. Lollapalooza was not just a chance to perform in front of thousands of people in their hometown. It also served as an opportunity to introduce their musical identities and prove once and for all the city is more than just the singular genres (drill, bop) or crews it facilitates.


Things kicked off Thursday with a rowdy set from Towkio. Performer Preston Oshita’s energy pushed through the downcast and rainy skies and the audience returned that energy as the show progressed. Oshita bounced across the stage while performing old hits from last year’s .WAV Theory or new cuts from Community Service 2, his new EP released in July. Oshita is fun and lively. At Lollapalooza, he made full use of his too-brief 45-minute set from top to bottom, not letting a single second go to waste.

The following day, Saba and Joey Purp performed early. This has been a pivotal year in each artist’s career, and each took the opportunity to seize the stage with enthusiasm. Purp, a last-minute addition to the festival, is still riding high on the success of his iiiDrops mixtape from May, and his show was a distillation of that same energy.


Saba in particular, though, was an early afternoon treat, providing some of the most gorgeous and interesting music of the weekend. His songs were filled with fluttering synths, sugary melodies, and a flow and rhythms that wash over the listener in the best possible way. With Saba, attendees were given a chance to listen to a different, albeit still compelling representation of Chicago hip-hop. Saba’s Lollapalooza performance proved he has one of the best opportunities to translate beyond the limitations of the city.

Joey Purp

Running linear through his music is a level of sophistication nearly unmatched by his peers. His music ripples in the ear of the listener. As his set progressed, curious listeners continued to gather at the stage. There is a certain energy and presence there that might be missing from other performers. He is charismatic but also extremely kind to his audiences, engaging with them on what feels like a peer-to-peer level.

Throughout the weekend, Smino utilized the help of his team (or maybe just his friends) to promote his show. I regularly saw young men carrying signs advertising the time and date of Smino’s show. Although he is not originally from the city (he hails from St. Louis), the young rapper has spent a considerable amount of time within the city, first attending Columbia College and later performing regularly at different venues and clubs. Still, this Lollapalooza set proved to be something of an introduction of the musician to festivalgoers. His performance was early in the day at noon–a less than ideal time–yet he utilized every opportunity to show exactly what he is made of: unbridled confidence, intelligent diction and a dexterous artistry that pushes and pulls between rapping and singing.


Vic Mensa

Vic Mensa’s headlining set on the Pepsi stage on Saturday night was the most compelling, possibly of any artist, during the festival. Unlike his peers, Mensa crafted a well-rounded stage show tackling issues of racism, inequality, violence, and mental health with deliberate care and artistry. He set the tone by dedicating his show to Laquan Mcdonald and directly calling out the Chicago Police Department at the start of his set. The young fans in attendance were perhaps more oblivious to the still-festering repercussions of Mcdonald’s untimely and unjustified death, but that made his approach all the more important.

A cacophony of dancers clad in riot gear appeared throughout the hour-long performance. Sometimes they pushed and pulled against Mensa’s body, crowding him, hovering over him as if he was not a human being but a thing, an Other to overpower. Even in quieter songs that grappled with Mensa’s personal struggled and were pulled from his latest release, There’s A Lot Going On, the police flaunted their chests. They jerked slightly as if to grab their weapon and lunge toward Mensa’s body to make sure he didn’t get out of line. Mensa was a Thing to maintain, both as an artist expressing himself and as a black man in a hypersegregated city and country.

Hovering over the performance was the very real truth that these acts are lived experiences. This is someone’s (many someones’) reality. And if you are not from the city, or if you live within its confines but away from the worst of it like in the gleaming downtown in which the music festival takes place, this performance was a chance to show just how omnipresent law enforcement can be in people’s lives. Chicago’s segregation is a deliberate choice both by the average people living within it and the people in charge of controlling, patrolling, and defining it. Our hypersegregation is not just self-imposed distancing. It is the separation of medical care, of transportation, of educational opportunities. It is the separation of housing opportunities, employment opportunities, and opportunities of self-care. It is the separation of living and being alive.

Later, Mensa invited Lucy Stoole, a host and performer in Chicago’s LGBT nightlife scene, to “marry” two of the very same riot police officers on stage during a performance of “Free Love.” This new track, released during Chicago Pride and in response to a family member of Mensa coming out, continues to emphasize the Chicago artistry Mensa aims to explore: diverse, expansive, poignant, and pointed.

Chicago is a sprawling forever city, a place that seems to go on and on, a place consumed with bouts of quiet and character and difference. Lollapalooza 2016 gave local musicians the opportunity to connect the disparate communities, scenes, and sounds of the city under one festival. Each was different in their own way and more importantly, each utilized their time to tell a story–whether joyful and spastic, raw and quirky or heavy and emotional–true to their existence shaped in and around the city.

Petya Shalamanova is a photographer based in Chicago. Follow her on Instagram.

Britt Julious is a writer from Chicago. Follow her on Twitter.