Connecting Through Content: A Belated Thank You to Gary Stewart

I mostly remember how flabbergasted I was. How someone I didn’t know very well could give me such a kind, generous and thoughtful gift.

The gift was two box sets: One was every season of Deadwood on DVD and one was the epic Freaks & Geeks. (This was before streaming TV.) I lent the Deadwood set to someone and never got it back. I finally watched Freaks & Geeks during the pandemic, on Hulu, and loved it.

The physical gifts were absorbed by my life and overall distraction at the time. With a child on the way and a new job, I barely knew what day it was, let alone have time to watch TV. And forget about following up with the person who made the recommendation in the first place to tell him how much I enjoyed it. I didn’t seem capable of a thought like this.

Now I badly want to say thanks. But I can’t.

The person who gave me these gifts was Gary Stewart. We worked together briefly in 2006 when we were both in the editorial department at iTunes. I don’t remember what I did or said that made him act so thoughtfully toward me. Gary died by suicide in 2019.

Even after his death, I did it again. A tribute CD was sent to me, and I put it on the shelf without much more than a cursory look. The disc blended into my frozen-in-time CD collection. This week, however, while bored on my Peloton, I turned to my left and saw it there. Curious, I pulled it off the shelf and read what it said. The notes stopped me in my tracks.

This person! He understood the profound impact of connecting people to pop culture they might love and what a service that could be for anyone who entered his orbit. He knew you could light up someone’s life with a thoughtful recommendation that showed that you took your job as a matchmaker seriously. As someone who knew him well said on LinkedIn: “He understood, more than most, that a pop culture connection was a human connection.”

Although I’m nowhere near as knowledgable as Gary was, I too feel in my bones the power of pop culture to bring people together. “You’re not strangers if you like the same band” is a phrase that I love and know to be true. It is *so satisfying* to connect with people over an addictive TV show, a new song they’ve just gotta hear, or a book that’s impossible to put down. And if you’re the one recommending it? Wow, you just made someone’s life a little better.

I’m really sad that I missed the chance to connect with a kindred spirit, especially when it might have really mattered, just because I was too scattered and “busy.” I didn’t know Gary very well or for long, but now I get it. I understand the power of a recommendation when it hits, both for the giver and the receiver. At minimum, the gesture says: “Hey, I was thinking about you, and I think this might make you happy.”

What a beautiful act.

Thank you, Gary.