My biggest uncertainty while contemplating my 18th consecutive return to Chicago’s corporate-sponsored youth extraction machine known as Lollapalooza isn’t whether there will be enough actual guitars on site this year to justify calling it a music festival. It’s whether I should wear knee support over the four-day slog.

Like every middle-aged casualty of time and poor life choices, tennis elbow killed my tennis career in favor of pickleball, and my knees have been filing formal complaints about vertical activities. Matt, my somewhat more youthful festival accomplice for the past 12 years, offers his assessment: “The only thing worse than an old bastard at Lolla is an old bastard with a knee brace.”

He’s not wrong. But here’s the better question: Aside from the 30,000 daily steps that will briefly convince my fitness tracker I’m not completely sedentary, and considering a lineup dominated by EDM button-pushers and pop music algorithmically designed for TikTok attention spans, why do I keep subjecting myself to this elaborate form of cultural masochism?

The rational answer is that I shouldn’t. I’m demographically irrelevant to an event that sells overpriced water to people who think mumble rap represents artistic evolution. Yet here I am, planning my annual pilgrimage to watch teenagers discover music that peaked before they were born, while standing in crowds designed for people half my age and twice my tolerance for bass drops.

The explanation is embarrassingly simple — this annual corporate cash grab wedged between Chicago’s magnificent skyline and pristine lakefront has somehow managed to create genuinely irreplaceable moments despite the festival industry’s best efforts to sanitize all spontaneity out of live music.

I’m not talking about the manufactured “festival experiences” that get packaged for Instagram stories. I mean the kind of cultural accidents that happen when you cram 100,000 people into Grant Park and occasionally something transcends the demographic targeting and profit optimization. The setting helps — there’s something about music echoing off Lake Michigan while the city watches that makes even mediocre performances feel momentous.

It’s completely irrational. I should be home, protecting my lower back and my bank account, streaming whatever these artists recorded in actual studios with professional sound engineering. Instead, I keep returning to this overpriced outdoor concert series because every so often the corporate machine facilitates genuine magic.

Consider these moments…

Lollapalooza 2008: The Year Everything Clicked

It came to me at my first Lollapalooza that everyone else had been doing festivals wrong. When Radiohead took the stage with nobody scheduled against them — because what lunatic would program competition against peak Thom Yorke? — fireworks literally erupted behind the band during “Fake Plastic Trees.” It wasn’t planned by the festival. The universe just decided to punctuate musical perfection.

Shortly after sunset, “15 Step” kicked things off with Jonny Greenwood lurking behind a black hoodie like some kind of guitar-wielding specter. Any whispers about Yorke’s health evaporated instantly as he twitched and clapped through the In Rainbows opener with manic precision. Ed O’Brien turned the crowd into participants, filming them with his camera and projecting their faces onto screens — participatory democracy through rock stardom.

They played the entire In Rainbows album, which in hindsight feels like watching someone unveil a masterpiece in real time. The light show during “Arpeggi/Weird Fishes” created an underwater dreamscape — blue aqua haze punctuated by white dots that made Grant Park feel like an ocean floor. When multiple band members grabbed drumsticks for “There There,” you realized you were watching musicians who understood performance is theater, not just sonic reproduction.

But the fireworks during “Fake Plastic Trees” transcended festival logistics and entered genuine cultural moment territory. Thousands singing along while Yorke worked his acoustic with brilliant colors exploding behind the stage during both the crashes and the quiet parts — this was why live music matters. You can’t stream spontaneous magic or algorithm-generated collective euphoria. Indeed, it was my most memorable moment from hundreds of live performances.

The entire festival was curated intelligence at work. Kanye was peak Graduation-era Kanye, before he became a walking Twitter meltdown. Rage Against the Machine created mosh pits so intense that humans were being launched over barricades like some kind of physics experiment in crowd dynamics. The security chief actually had to interrupt Zack de la Rocha mid-rant, which somehow made the whole thing more authentically Rage.

What struck me most was the lineup’s confidence in lasting relevance. Brand New, Wilco, Nine Inch Nails, The Raconteurs — these weren’t flavor-of-the-month bookings designed to maximize streaming metrics. They were bets on artistic substance that have aged beautifully.

The 2008 lineup captured this perfect storm moment when indie rock still mattered, hip-hop was asserting cultural dominance, and electronic music hadn’t yet devolved into algorithmic button-pushing. Radiohead’s “pay what you want” In Rainbows experiment had just proved artists could bypass industry gatekeepers without sacrificing artistic integrity. Kanye was riding the creative peak that produced “Stronger” and “Good Life.” Rage was proving political fury could still pack amphitheaters 15 years after their debut.

This was Lollapalooza as intellectual curation instead of demographic targeting — before data analytics completely colonized lineup decisions.

2014: Hip-Hop’s Hostile Takeover

The 2014 lineup reads like someone finally figured out that rap music might be culturally significant. Eminem and OutKast as co-headliners, backed by Nas, Run the Jewels, Chance the Rapper and Childish Gambino — an acknowledgment that hip-hop had become America’s dominant musical export.

The non-rap acts weren’t afterthoughts either: Interpol, Spoon, Arctic Monkeys,and a pre-fame Courtney Barnett created a fascinating tension between indie rock’s last gasp and hip-hop’s cultural ascendancy. Even the pop choices felt intentional — peak Lorde, The 1975 before they became insufferable, Broken Bells at their most accessible.

The surprise Eminem-Rihanna duet on “Love the Way You Lie” was one of those moments that reminded you why live music matters. Two global superstars acknowledging each other’s craft in real time, no autotune safety net. It’s the kind of spontaneous collaboration that streaming platforms can’t manufacture and social media can’t duplicate.

2016: Expansion Anxiety (From Three Days to Four) and the Girls on the Swings

The first year of the four-day experiment felt like watching a startup scale too quickly. More days didn’t necessarily mean better curation — it just meant more opportunities for mediocrity to creep into the margins. But when 2016 worked, it worked spectacularly.

Radiohead and Red Hot Chili Peppers anchored things with the kind of headliner gravitas that feels extinct now. LCD Soundsystem’s reunion tour was peak nostalgia executed with genuine artistic purpose instead of cash-grab cynicism.

I had decided to bring my 13-year old son that year as Lolla had always been a safe and joyful experience for me, but I had not considered all the variables. I had introduced my son to Jane’s Addiction by singing “Been Caught Stealing” from the age of five, so the chance to see them together seemed a layup. What I didn’t foresee was the NSFW stage show. I have since become a better parent.

The Chicago talent showcase was particularly smart — Vic Mensa, Louis the Child, Flosstradamus. They represented hometown pride without the usual local-act charity booking feel. Billing Future second-line now seems like festival programming malpractice, but in 2016 he was still building toward his streaming dominance.

The expansion created scheduling conflicts that revealed uncomfortable truths about festival priorities. More isn’t always better, but sometimes it’s the only way to discover what actually matters.

2021: Pandemic Pragmatism

Holding any festival in 2021 required either tremendous optimism or spectacular delusion. Lollapalooza managed both, delivering a lineup that acknowledged reality while refusing to lower standards.

Tyler, the Creator and Foo Fighters as headliners made sense — Tyler representing hip-hop’s creative evolution, Foo Fighters providing reliable rock professionalism when reliability felt scarce. Miley Cyrus brought the kind of unpredictable energy that live music had been missing during lockdown hibernation. Billy Idol and Wiz Khalifa were surprise guests to her headline performance.

But the “complicated circumstances” showed. Too many other artists felt like placeholder bookings — Surfaces, Jack Harlow, Oliver Tree — representing that bland viral-artist category that prioritizes compatibility over artistic substance. The pandemic had compressed everyone’s tolerance for risk, leading to safer, less-adventurous programming.

Still, any festival that managed to happen in 2021 deserved credit for logistical competence alone. The fact that the post-pandemic coming out party featured genuine artistic moments despite some corporate compromises felt almost miraculous.

***

So there it is — 18 years of financial masochism disguised as cultural engagement. Every August, I voluntarily submit to overpriced everything, demographic irrelevance and the slow death of guitar-driven music, all while my body files increasingly urgent complaints about prolonged standing.

But that’s exactly why these moments matter more now than they did when I was the target demographic. In an era where algorithms curate our entertainment and AI generates our content, the possibility of genuine surprise becomes exponentially more valuable. When corporate programming accidentally facilitates magic — when fireworks spontaneously explode during “Fake Plastic Trees” or when Eminem brings out Rihanna unannounced — you’re witnessing the kind of cultural accident that can’t be manufactured, streamed or duplicated. These aren’t just memories; they’re proof that human experiences can still transcend corporate optimization.

This year, I am really looking forward to Ratboys.

• Lollapalooza Day 1 (Thursday 7/31): Headliners are Luke Combs and Tyler, the Creator. The rest of the bill includes Cage the Elephant and Ratboys.
  
• Lollapalooza Day 2 (Friday 8/1): Headliners are Korn and Olivia Rodrigo.  
  
• Lollapalooza Day 3 (Saturday 8/2): Headliners are Rüfüs du Sol and Twice. 
  
• Lollapalooza Day 4 (Sunday 8/3): Headliners are Sabrina Carpenter and A$AP Rocky. 

Complete lineup at www.lollapalooza.com/schedule   

Author’s Note: Special acknowledgement to Selena Fragrassi, Chicago Sun-Times music critic. Her July 25 Lollapalooza lookback article inspired this story. Selena has been covering the music scene for 15 years. Her bylines have also appeared in SPIN, Loudwire, Paste, Nylon, Popmatters, Blurt, Under the Radar and Chicago Magazine. Selena is a voting member of The Recording Academy.