The year I attended was 1992. That was GenCon's 25th anniversary. In fact, I ran a couple short role-playing events at that convention. One interesting tidbit was that I bought a painting from Mark Poole at that time. It's hanging over my fireplace.
Anyway, Mark was at this convention, too. I got to show him what I had done with his work (that, incidentally, also graced the cover of Dragon magazine #201, which sits on my mantle).
My wife loves meeting artists and actors and authors. They're just regular people, but to her they're special.
Also special were the two days I got to spend with my daughter absolutely geeking out. Everyone we met was gracious and accommodating. As much as she enjoyed just spending time with her dad, Sarah was surprised at the spectacle that is GenCon. She expected rooms full of sweaty, middle-aged men playing board and role-playing games. What she found were tens of thousands of people who absolutely overlook one another's quirkiness.
You may have never seen a Utilikilt anywhere else. There, you'll find several people wearing them without irony or comment. You can meet game designers, artists, authors, and musicians here. Beyond gaming, you also have anime and cosplay.
Another aspect of the convention that my daughter found noteworthy was the breadth of attendees. Old and young, male and female of all races and ethnicities. Although I would say that Caucasians were over-represented.
Without further ado, here are the pictures.