When I get past the gates, I am immediately overwhelmed, my sight overloaded by summer citrus colors and the blurs of passing faces. My only prior experience with a music festival was Loufest, which now seemed fairly podunk and lame in comparison. There is stimulation in every direction. In addition to the frankly massive crowd and eight main stages, there is the FYE Music Experience Tent, the Bud Light Dive Bar, the Fruit of the Loom Human Claw Experience, the Cupcake Vineyards’ Poptail Shop, Neighborhood of Good® Brought to You by State Farm® and the Toyota Sienna Festivan Wonderland Presented by SiriusXM, as well as a dizzying array of local restaurant booths. Feeling a little paralyzed by all the options, I decided that while I wait for my friends to arrive, I would check out the press lounge. I can’t pretend that it didn’t feel good to be able to flash my credentials at the burly sunglasses-sporting guard as I walked into the restricted area, but that feeling of confidence was quickly displaced by a strong sense that I did not belong in this world of lanyards and golf carts and professionalism. I relieve the press lounge of some of their complimentary drinks and am on my way.

I receive word that I am to meet my friends at the Perry’s stage, the designated home of most EDM acts at Lollapalooza. The first thing I notice is the stench: The whole field was suffused with an odor I can only describe as biological. The second thing I notice is the distinctive nature of the crowd at Perry’s, which appeared to have the lowest median age and the highest median family income of any stage (also, I would wager, the highest volume of body glitter per capita). London on da Track was performing a DJ set and doing a pretty good job of it, his hip-hop-based sound going over well with the young Lollapaloozians. I (briefly) joined a mosh pit, which, while certainly of a bizarrely milquetoast variety given the crowd and environment, was fun nevertheless.

After some difficult scouring in a remarkably homogeneous crowd of Lollapaloozians, I’m able to find my friends from home along with a blue-jawed, shirtless man I don’t recognize — one comes up and whispers to me that his name was Hunter and that he bought them drinks and that as a direct result he was to be our friend for the time being. One of my friends vouched for his character by informing me that he had yet to drug them. This turn of events did not end up bothering me as much as I thought it would — he turned out to be quite the entertaining character. Hunter had a psychedelic tank top of a lurid metallic hue that put all other colors to shame (I say “had” rather than “wore” as it spent most of its time tied around his backpack rather than on his torso). He wore a hat to cover his heavily receding hairline. I don’t think I ever saw him take off his sunglasses. Hunter was a self-described professional drug dealer in his thirties who viewed himself as a festival veteran. His duty was to help everyone else have fun. He came alone. While at first his behavior seemed obsequious, as I became more and more intoxicated off of the free alcohol he provided us I started finding him to be better company. Hunter possessed many peculiar mannerisms, including but not limited to a tendency to skip as his mode of transportation whenever he went off to buy us more $30 plastic bottles of wine and a strangely servile attitude (such as picking up all the trash on the street around us when we sat down on the curb to eat). When I pressed him on this, he reassured me that “it was his job” to ensure that we had a good time. He refused to accept payment for the alcohol, claiming to have made over $8,000 that week alone. While he was ostensibly quite friendly, there was something undeniably unctuous about Hunter, and I can’t say that I was disappointed when we parted ways.

Billie Eilish

We arrive at Billie Eilish, who I will admit I was very excited for. She drew what was apparently an unexpectedly large crowd, as she was placed on the fairly small Tito’s stage.

When we got there, it was her brother Finneas on stage performing an unknown solo song of his. This was not a crowd-pleasing number — they had clearly come to see Billie, not her brother. His stage presence was overly serious and unintentionally comical.

Eilish’s performance, however, was not a great one either. Her vocals seemed enervated and her stage persona was eye-roll-inducing. I overheard a significant amount of Lollapaloozians complain of boredom as they left, despite the fact that a great portion of the crowd was filled with adulating fans who knew every word to every song. I think at least 90 percent of the crowd was singing along when she played “Ocean Eyes.” I’ll forgive Billie Eilish for her rather affected stage presence given her inexperience and young age (at 16, I was trying to figure out how to smoke weed out of an apple and spray painting the walls of parking garages). At the same time, I wish I had gone to see CHVRCHES instead.

Petit Biscuit

I was able to catch a little bit of Petit Biscuit’s show in between Billie Eilish and Khalid, located at the American Eagle stage. My favorite area at Lollapalooza, the stage is located in the middle of a thinly-wooded grove that provides some atmosphere and respite from the searing Midwestern sun. All weekend long, daring Lollapaloozians were scaling the trees and watching from the elevated vantage, a situation that imparted the effect of great importance to the performance at hand. Petit Biscuit’s show (from what I saw of it) was quite good; his particular brand of buoyant atmospheric house was turned up a notch for this performance, infused with more energy and bounce than his cinematic studio renditions.


Khalid, who had earlier made a surprise appearance during Billie Eilish’s set to perform his part on their joint single “lovely,” took to the Bud Light stage for his time in the spotlight. His show was pleasant but uninspiring. The most salient component of his show was when a fearless young man scaled a large pylon of unknown purpose, attracting the attention of a good portion of the audience. He proceeded to do some pull-ups off of the overhang (probably about 40-50 feet off the ground), which was insanely cool. I once again found myself wishing I had stayed on the other side of Grant Park and caught Rezz’s show instead. We decided we would wait at the Bud Light stage afterward in order to procure a good spot for Travis Scott’s show, for which there would undoubtedly be fierce competition.

Travis Scott

Travis Scott was one of the most anticipated shows of the night, both due to the imminent release of the long-hyped Astroworld and his infamous reputation as a live performer — last time he performed at Lollapalooza, he was arrested after inciting a riot a mere five minutes into his set. The atmosphere was electric. I was at a level of drunken vigor that was perfect for the occasion, and someone dished me out some apple-flavored vodka out of a lotion bottle — things were starting to shape up nicely.

He opened with “Stargazing,” a single off Astroworld released a day or two ago that a great deal of the crowd already knew the words to. “Mamacita” and “Dark Knight Dummo” were the highlights of the show, both Travis and the crowd utterly fervid. 

It was a performance with high highs and low lows, the lows mainly consisting of Travis slowing the momentum with a few bemusing moments of protracted crowd interaction. The first involved a guy named Steve in a Phoenix Suns jersey who managed to get up on stage — at first Travis told him to do a stage dive, later recanting this suggestion after what looked like some intense thought led him to realize that Steve could not execute such a stunt without serious bodily injury. Steve, for what it’s worth, absolutely blew his shot by ignoring Travis’s increasingly urgent entreaties to stop trying to take pictures with him, slowly but surely drawing the snarling ire of both Travis and the crowd. Steve’s time in the spotlight lasted around five minutes, ending with a half-assed stage dive that pleased no one. The second baffling event involved a man Travis brought up on stage who went on some extended, indecipherable rant that concluded with him proposing to his girlfriend who was apparently in attendance. I don’t think I’ve ever felt such acute second-hand embarrassment as I did for our friend onstage when he was waiting for his (potential) fiancée to come up — the general sentiment in the crowd was that she had dipped out. Eventually, thank god, she does emerge from the crowd, and the happy couple awkwardly embrace. “This a beautiful moment,” Travis muttered in such a way that it sounded like he was trying to convince himself. “Play Astroworld!” someone yells.

Say what you will about these unwise interludes, one aspect of Travis’s character that is indisputable is that he cares about his fans and his music. He was not afraid to call the V.I.P. section out for their elitist lack of engagement; he seemed to interpret their lack of energy as a manifestation of feelings of superiority. He just wants everyone to rage. You can imagine him as he started out — a teenager alone in his dark four-cornered room illuminated only by the cold light of his screen as he tried to get out all the fire inside him, just wanting to be like Kid Cudi.

The energy in the crowd only reaches the heights it was at prior to these interruptions for “goosebumps” and “Antidote.” Travis closes the show by debuting a new song off Astroworld (which turned out to be “5% Tint”). I walked away longing for the explosive passion of those first few numbers and wishing Steve had decided to stay home that night.


Tyler, The Creator

I find my friends sitting on a different gentle slope and we head to Tyler, The Creator’s set. Tyler was predictably energetic and engaging, but given that his show was very Flower Boy-centric, it wasn’t as wild a performance as he is known for. I wouldn’t say this is a bad thing; it’s the natural product of his newly mature music. He seemed eager to shed the persona based around controversy and insubordination he assumed during his early career.

Post Malone

Post Malone cut a likable figure even if I wouldn’t describe his stage presence as commanding. His performance was fun in spite of some lowlights, although I doubt it would have been enjoyable if you weren’t a fan of his music already. I was separated from my friends, but I was able to find a stranger donning a woven burnt-orange poncho to share my noxious vodka in their absence.


Brockhampton attracted both the youngest and most zealous crowd I had seen so far. At one point, I was caught in a mosh pit that was led by a kid who can’t have been older than 14, his face beet-red with subtle purplish-blue webs under his watering eyes formed by broken capillaries. There are a lot of die-hard Brockhampton fans out there apparently, and most of them wear checkered Vans.

The National

While seemingly everyone went to see Bruno Mars, I trekked over to The National, a show I had been waiting for all day. The average age jumped up by about 20 years between this show and Brockhampton; the crowd was also remarkably small — it felt almost intimate. I was able to be three rows from the front despite arriving slightly after the show had already begun. While the crowd was small, it was mainly filled with fans of The National (most, if not all, non-fans had eschewed this show in favor of Bruno Mars).

Matt Berninger’s stage personality is certainly colorful. At one point, he riffed that he was “actually wearing a new fragrance tonight. It’s called Manafort;”— he takes a slight pause —“it stinks of self-loathing and betrayal.” This absolute fucking trainwreck of a joke caused the man in overly-small glasses next to me to erupt in glee. Matt made frequent trips off the stage down to the crowd to mingle; he also made a few attempts to crowd surf, I think. It was hard to tell whether he was trying to get carried or whether he was simply collapsing into the crowd, as he seemed to be very drunk.

Bryce Dessner absolutely killed it all night, in spite of Matt throwing his drink all over him and his equipment in the middle of the set, in turn causing a fretful-looking roadie to spring out from his backstage crevice to hurriedly clean off the vulnerable electronics (with the unhelpful but well-intended assistance of Matt). Aaron Dessner and the Devendorfs performed flawlessly as well. In spite of his lame attempts at resistance humor and the anxiety he caused the technical staff, Matt Berninger had a great night. The National are experienced performers of undeniable quality, and I enjoyed their set greatly.


Daniel Caesar

Daniel Caesar, whose performance proved to be quite a soothing experience, is brilliant and his voice seraphic; his style doesn’t lend itself to a massive music festival, tender moments became muddied. It sounded like there were some problems with the mixing on his audio as well, his vocals often buried.


Logic is a little too easy to dunk on, so I’ll refrain from doing so. I will say that he has a great relationship with his fans — he loves them and they love him. So at least they both have someone. 

Vampire Weekend

I got a lobster corn dog. It was the best thing I ate all weekend. Grant Park had at this point taken on a subtle saffron hue as the sun set behind the jutting Chicago skyline, and while my friends all went to go see the brooding Weeknd, I walked across the park to Vampire Weekend, who I’ve best heard described as “a boat shoe you don’t hate.” It was more crowded than The National’s show last night but was suffering from a similar phenomenon of being up against a pop titan. Ezra Koenig walked out in his System of a Down long-sleeved tee and grey cargo shorts and kicked off the show by playing “A-Punk” three times in a row. It got better with each rendition and the crowd got progressively wilder. This was the most Vampire Weekend-esque way they could have opened the show, and frankly, I’m here for it.

They played their classics with consummate elegance, every song well-received by the crowd. Their personality burst through in little jocular moments such as a brief bass solo that included the “Seinfeld” theme song.

I exchanged some unpleasantries with a chipper man in a camo headband who looked like he was looking at your eyes rather than into them when he spoke to you and was trying to maneuver his way to the front of the thick crowd by pushing his wheelchair-bound friend. The same guy had cleverly informed me before the show began that his friend wasn’t actually injured, a divulgence that requires the level of discernment one would expect from the type of person who would try a move like that to begin with. He accused me of not having a sense of humor about the whole thing. Having already used up my body’s dopamine supply for the night and feeling less than intimidating behind my sapphire heart-shaped sunglasses that I had discovered on the ground earlier — a little dirt-encrusted, but wearable — I decided to forgo a response (he was eventually dispatched by someone else in the crowd). Aside from that guy, the audience was one of the most upbeat and positive I was in all weekend.

Vampire Weekend felt fresh off of a long touring hiatus, announcing that their fourth studio album was imminent (in the process of being mastered). They closed with “Walcott,” a fan favorite.


Rex Orange County

Rex Orange County drew a massive crowd of Lollapaloozians relative to his early time slot, evidence of his skyrocketing popularity (particularly among the checkered Vans crowd). Rex Orange County feels wholesome and authentic, and in the shaded grove of the American Eagle stage, his show was idyllic.

Chris Lake

The barebones house music of Chris Lake sounds like what plays during a club scene in a movie, which isn’t intended as a compliment. I jumped up and down and pointed at the sky rhythmically anyway; it was fun.

Portugal. The Man

Portugal. The Man are great live performers, and they seemed to possess a sense of total confidence. They artfully weaved snippets of covers into their own work, including “Gimme Shelter” and “I Want You (She’s So Heavy).” It’s easy for bands who draw too much influence from classic rock to feel atavistic and uninspired, but Portugal. The Man manages to evade that common pitfall. I spent most of their performance idly listening while people-watching, an activity which Lollapalooza is made for. I saw an infant so young that I can only assume they were just delivered in the on-site medical tent, I saw an elderly man walking through Grant Park wearing a business-casual outfit — white oxford shirt and black dress pants, carefully creased — listening to his earbuds, seemingly oblivious to the fact that he was in the thick of one of the largest music festivals on the planet, Buckingham Fountain now a gorgeous anachronism backdropped by the gray city.


I joined the procession over to ODESZA for the grand finale. We were accompanied by a coalition of rainbow-clad ravers, friends of a friend. The girl who was clearly the ringleader of the group moved like a predatory animal, darting in and out of my field of vision like a viper snatching at its prey. Her chestnut hair was intertwined with some type of metallic golden material.

ODESZA is quite possibly the best live performance I have ever seen, the production value surpassing that of any other artist I saw all weekend. They opened with “Intro/A Moment Apart,” replete with triumphant brass additions and bright white lights that gave the performance a near-baptismal effect. Their already cinematic music was made even more so through the strategic use of a drum line and other live orchestration. Each song was accompanied by synced visuals; glitched-out celestial graphics, flashes and specks dancing across the screen, occasional pyrotechnics in moments that carried particular climactic weight. It was beautiful, and a fitting conclusion to my time in Grant Park. 

Leave a comment

Your email address will not be published. Required fields are marked *