The Joy (and Terror) of Going to Lollapalooza With a Teen

I said yes to this father-son outing because it seemed like a rite of passage. Charlie’s reached that age when he’s starting to lose interest in his mom and me. There’s been research that parents who listen to music with their kids have better relationships, especially as their children start to shift into young adulthood. I desperately want that connection. And OK, I also wanted to prove to Charlie that his dad is still cool. I don’t know much about the music he discovers on YouTube or TikTok. But Lollapalooza? I was here near the beginning. I was here for the festival's second outing, when the organizers were still blazing a trail and the word "Lollapalooza" wasn't part of the mainstream vernacular yet. I’m as OG as this festival gets.

I hoped he’d have questions about the pre-internet Lollapalooza from the 1990s. “Did Soundgarden really do a cover of Body Count’s ‘Cop Killer’?” “Did the audience actually rip up the lawn and toss sod into the air during Ministry’s set?” Well, yes, son, come closer and let Papa tell you about the Old West of alternative rock in the early ’90s.

But Charlie didn’t have any questions. He just wanted to see his bands and hear his music. As the day wore on, I felt less like an elder statesman with lessons to share and more like an awkward third wheel with back pain. Charlie tolerated me, but he absolutely didn’t want to hear my Lolla war stories.

The writer and his son attended the 2024 Lollapalooza music festival held in Chicago's Grant Park.

Taylor Regulski/Lollapalooza

Charlie and I walked what felt like 2 miles to the next stage to see a band that I probably would’ve loved in my youth, but in 2024 seemed unnecessarily screamy and loud. The amount of cannabis smoke in the air was starting to make me physically uncomfortable.

It’s a weird thing to witness the circle of life play out in real time. I know I’m getting older, and I know my son isn’t a child anymore. But Lollapalooza brought both of those things into sharp focus simultaneously. I thought I’d be ready for this, but I’m really, really not ready for this.

We somehow made it to the final performance — the Killers, the only band in the lineup that I vaguely recognized — and I was lumbering like an underslept Frankenstein monster late for his colonoscopy. Charlie weaved through the crowd, zigzagging like he’d been doing this all his life, and I struggled to keep up with him.

“Stay where I can see you,” I yelled, but the warning didn’​t have as much authority in his teens as it did when he was 6.

I lost him for a moment in the throng of bodies, and I panicked. I didn’t have the energy to yell over the din, and all I could hear was the blitzkrieg crash of guitars. Then I felt his hand. Charlie gripped me hard, like he used to when he was a toddler and scared, and pulled me close to him. He still watched the stage, smiling and laughing and singing along, but below the sight lines of his peers, our hands were practically fused. 

Was the surreptitious hand-holding for him … or for me? Was this his last moment of boyhood, one last grab for Daddy before he tumbled into adolescent independence? Or was he making sure his aging father, who clearly signed on for more than he could handle, was OK? I didn’t know — and honestly, I didn’t think I was emotionally prepared for either answer — but at least for now, I was OK with splitting the difference.

“I’ve got you,” I whispered to him over the deafening guitars.

“I’ve got you too,” he whispered back.