D&D: art vs play

This was the very first image that I ever associated with Dungeons & Dragons.

I encountered it when my older brother brought home a 1981 Moldvay Basic set from KB Toys with hard-earned cash from mowing lawns (I bought a tauntaun with mine).

The image was fascinating.

  

The magic-user's face reminded me more of Jadis the White Witch than Princess Leah or any other female hero I'd ever encountered.
  

The dragon lacked wings and was apparently aquatic.  

The warrior was so stoic that, unlike his companion, he appeared unconcerned about the fanged horror just a yard or two away ... in fact, he wasn't really even looking directly at the beast from what I could tell.  His goggled helm and beard reminded me more of Ming the Merciless than Prince Valiant.

                             

The second image that I ever associated with D&D was this one:

It too was striking.  None of the three adventurers were turned so that their faces were clearly visible, but rather it was easier for me to focus on the hobgoblins (for whom I eventually found myself rooting--they were more relatable as they defended their territory against attack).  By age six, I knew a bit of history ... enough that I thought the armor of the explorers was odd ... more Classical than Medieval.

Another thing I noticed about these images by the time I was 10 or 11 was how sharply they contrasted to some aspects of the D&D game.

In actual play, we readily spent every last gold coin equipping new characters and carefully calculated our encumbrance values so that we knew just how fast we could run away from pursuing critters.  The adventurers in D&D art, on the other hand, seldom had more than two or three pieces of gear on them.

not a backpack in the whole bunch

"That guy would never survive.  All he has is a bow!"

The cleanness and simplicity of the art was lost on younger me as I looked for  (and seldom found) images that matched my experience of the game.

Sometimes I'd even invent a narrative to explain a piece that I liked ... "Maybe their mule, supplies, and retainers are just out of sight to the right."

This "problem" persisted over into miniatures too and, though we mainly used them to record marching order or simply as display pieces, the incongruity was still there.

I picked up Swords & Wizardry Whitebox last year, not because I needed another rules set (my Moldvay is in fine shape, I also have that text in pdf, and I occasionally carry a copy of Labyrinth Lord just in case I want a spell reference, wandering monster chart, or treasure table), but mainly because I was charmed by the digest-size, minimalist approach, and simple (almost naive) artwork.  

as lovely as it is simple

Clearly D&D artwork remains very distinct from D&D play.

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Why do you suppose that, with exceptions like Jim Holloway's contributions, D&D artwork has tended to remain heroic or mythic rather than reflective of gameplay?

The dialectical relationship between art and play is strong.  How do you suppose that the "unencumbered hero" image has affected game play and changes in published rules?  

How do you suppose the rules as written have impacted gaming artwork?