I ended up at the Game Guild (game store in Lake Geneva) by chance on a school trip for a small group of people who had various social issues (I was in it because I had bad social anxiety in HS). Saw people playing D&D in the back room and as I started talking to them realized it was several of Gary's children and grandchildren and friends. So I would make the hour-long drive from the Chicago suburbs every weekend to play with them for a few years. It actually ended up being one of the biggest drivers for me getting past my social anxiety such that you'd never know I used to have it if you met me now. I ended up founding my own D&D group back home as a result and later in college. Both led to meeting lifelong friends and becoming confident in social situations, speaking, organization, etc. since I was DM most of the time.
A couple of my favorite stories...
- Bringing my best friend and watching him start arguing with Gary (without knowing who he was) about how Dwarven women don't have beards. Kicked him under the table and whispered "he made the f-ing game, if he says they have beards, they have beards!"
- Joking with some people about the various named spells like the spell lines for Bigby, Tenser and Mordenkainen and being confused why some of them seemed to be talking as if the spells were theirs. Turns out I'd been playing with the people who originally created and played Bigby, Tenser and Mordenkainen, so yes, they were their spells.
- Having Gary teach me a harsh lesson in physics and volume calculations when I cast a high-level fireball in a smallish space and incinerated half the party. He was not the most forgiving when it came to interpreting the rules.
- Being listed as an official playtester in the Lost City of Gaxmoor book.
Unfortunately, the Gygax family had a somewhat tragic history with businesses, and beyond what went down originally with TSR, the Game Guild itself (which his son Luke bought out at one point) seems to have fallen on hard times and is no more.
On a side note, I work at SmugMug right around the corner from you guys (we're near Evelyn and Pioneer right off the 85 exit), so if there's any interest in a HN D&D group, I might be convinced to dust off my dice bag!
Now that is a classic example of what we mean by whimsical tangent—the very best kind of tangent. Please tell us about that sometime!