In my 39 years of gaming, I've seen a lot of artwork. And as far as D&D is concerned, I've identified discrete periods that define the illuminations of the game: THE CORE RULES (1974): To call the art in the original D&D rulebooks amateur is an understatement. Sub-amateur better fits the bill. The pictures alternated between clever doodles and stuff that was clearly lifted from Marvel Comics. But there was a primal charm as well; one that conjured images of enthusiastic amateurs making their own fun. Fun, incidentally, that transcends the physical appearance of the finished product. Although the artwork depicted fantasy, it wasn't necessarily a fantasy that mapped well to the game's subject matter, and it never defined the experience in my mind.
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