Great story. One thing that hasn't changed in any edition is how much fun it is to roll a natural 20 in a tough situation.
Not to threadjack, but I wanted to share my story about playing with Mr. Gygax (and the title of the thread is Gaming with Gygax, after all!). It was years back at a con near Indianapolis (but not GenCon) that was having its first year. Guests of honor included Gary and my dad. I was living nearby at the time for college, and so my dad called me up and asked if I wanted to come. Partly it was to keep him company, and partly because he remembered years ago at another convention where he casually talked about hanging out with Gary- to which I said "You never told me you were friends with Gary Gygax!" to which my dad responded, "You never asked!"
So anyway, I eagerly agreed to go to the con. On Day 2, there was a panel where the guests were Gary and my dad. And I was the only one who showed up for the panel. I still think that's crazy- the con was just so poorly run, they couldn't get anyone to attend a small panel with Gary Gygax and Jack Chalker!
But it was lucky for me, because I got to listen in on an hour long talk between the two, telling stories about sneaking into graveyards during science fiction conventions to the real origin of D&D (Gary and his friends were playing a game with a neighbor who had polio when they were kids.)
Right there would have been an awesome story to tell for years to come, but it got better. Gary's son who had accompanied him to the con (whose name I don't remember, sorry!) came to remind him of the game of Lejendary Adventures he was scheduled to run. Gary said, "Well Jack, thanks for entertaining me. How about I entertain your son?"
I probably sat there for a few minutes with my mouth open.
The game had been scheduled in advance, and Gary was gracious enough to add me into what turned out to be an already overbooked game. Unfortunately, because of the sheer number of people, not a whole lot ended up getting done in the adventure, which started out in a very detailed town (mapped out on graph paper... how classic is that?) and eventually moved to some mysterious caves outside of town. We got through one fight in the caves before having to call it quits, but I still had a blast.
One thing that has stuck in my mind was embarrassing myself- I was talking to Gary's son in character, and I said something like "This place is boring, let's kick up some trouble." Gary overheard that and took it as me complaining, and said "Bored, eh? More of a hack and slash guy? We'll get to that." I felt like a huge ass, and tried to say that I wasn't bored with the game, but he already was moving onto other people in the (15 or so member) party.
Anyway, the whole experience other than that one moment was great, and I made sure to derail the next Friday's D&D game for a long time while I told the story, and it remains one of my favorite experiences of all time. About a year later, my father passed away, and I wrote Gary to tell him (finding him through ENWorld, actually). Gary was kind enough to write back with some stories and condolences, which really helped me get through it.
So any stories I hear about Gary running games for people who appreciate it always make me smile.