The weirdest part of the whole thing for me is that I've had a 30-something year obsession over this game, yet I've hardly ever played. Okay, I might have played one possibly solid game for 3 or 4 hours once as a kid at sleep away camp when it poured rain for a week straight and regular activities were cancelled, but that is it. D&D actually captures my imagination for numerous reasons, mostly concerning its rich content but also concerning its fascinating game-play mechanics (even though I've hardly played it at all). But all that aside, there's just something about the idea of it all... its imaginative nature, the pencils and paper and dragon dice, the idea of good friends gathering around a table for the night and sharing snacks while practicing decision-making and resource management, debating rules, and poring over densely-written rule books of spells, character class abilities, monsters and weapons tables, intricate dungeon and wilderness maps, combat encounters statistics, and last but not least - the artwork.
The old school artwork is to me one of the most fascinating and mysterious aspects of classic D&D's appeal. The look of it really gets me for some reason, which is also strange because technically speaking, it's considerably less awesome than the flashier art that came along later. There's a curious duality to the quality and charm of the older TSR artwork, in that while much of it is in its own way really great, that same beloved art might easily and understandably also be viewed as downright terrible... and regardless, I myself love almost all of it. It's a pretty strange phenomenon - how can it be both?
It's probably a common thing that we develop lifelong affections for things that really aren't so great according to conventional standards, simply because we form attachments when we're young that sometimes remain in our hearts for personal reasons no matter what. There are movies, for instance, that probably no one will agree are great but they stick with me because they struck a chord when I was young and gave me something I'll never forget. I was just a kid when D&D was first becoming really big - at that young age my sole exposure to such fantastical imagery was this very peculiar artwork released by TSR, and maybe I just didn't have much else to compare it to. I'm actually so drawn to the artwork that I have to look very hard to decide that maybe it does look as peculiar as it actually is. To me it just always seems so... right.
Isn't that one of the cool things about illustration, after all? There's no one solution to a visual challenge - there's no single way to communicate an idea or tell a story. The possibilities are endless, and oftentimes when an artist starts his or her wheels turning and begins to scribble and sketch, there's no telling where the ideas might ultimately lead.