For some reason D&D has never had good fluff, and I think the problem might be Gary's whole approach in the first place, which was very superficial. Sure, he knew a fair bit about myth and folklore but he just used it as a source for monster stats. The protagonists in his favoured fiction are rootless, ruthless individualists seeking gold, like oil industry workers in Robert E Howard's small Texas towns, spending all their money on drink and whores. Can you imagine a more shallow, pointless existence? This is the model for D&D.
Subsequent writers have taken Gary's jejune ideas and, nerds that they were, tried to make sense of it. Explain things, tie up the loose ends. Tell us what sort of hats gnomes wear and what flinds like to eat. Useless crap.
I certainly wouldn't call Greyhawk or much of the original D&D Mythology "shallow", nor would I call it Superficial, and I certainly wouldn't call Gary's ideas jejune. To be honest, a lot of the "well thought out" stuff was coming, but as D&D grew organically, it was hard to present a top-down view of everything.
And I hate to say it, but anybody who creates an RPG is a "nerd", Greg Stafford included. Let's not dismiss the people who aren't "avant-garde" as being lesser than those that are.
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