Like many of you, the art of early D&D played a crucial role in shaping my understanding of the game.
When people talk about art though, they tend to reflect on their favorite artists rather than examining how or why their art is meaningful. Let's take a moment to look at the three things most often depicted in D&D: monsters, characters, and dungeons.
With most of the early D&D artists being gamers themselves, they understood the lethality of the game. They understood how fragile their characters were in a dark dungeon surrounded by voracious, fearsome monsters. If I could generalize, the art was about the monsters or about the scene, not about the characters. Monsters normally overshadowed the depiction of PCs. They were larger and took up the majority of the visual space. They would be presented in the foreground and made a priority, or, their superiority would be emphasized by being positioned higher than the PCs. Monsters would also be depicted surprising or surrounding unwitting adventurers - a technique referred to as dramatic irony. Normally, monsters would be sticking it to the PCs in some fashion, such that the scene would provide a single over-riding message - things aren't going well and you are (more than likely) going to die. To old school D&D subculture, we could easily see the self-reflexive humour of it all. We, through the artists, were poking fun at ourselves and the situations we've all found our PCs in at one point or another. These were meaningful to us because they were evocative, otherworldly, and funny. In some cases, the worse the predicament of the adventurers, they more it peaked my interest. I don't think I was alone.
A similar approach was used with the representation of player characters. This is what I love about Stefan Poag's and also Pete Mullen's work today. Rather than gym-rats, early D&D artists depicted thin-armed adventurers who looked like they would have trouble holding up a sword (as an aside, I'm 6'5 260 lbs. I once tried picking up a legit 6' long two-handed sword and I couldn't even get the tip off the ground). So, when artists illustrated thin armed adventurers, they allowed us to see ourselves in the characters depicted. The PCs were accessible. This too was a self-reflexive form of humour. We/the artists were poking fun at ourselves. Just the thought of running around some dungeon trying to stay alive, wearing some snappy Erol Otus headgear, breaks a smile on the face.
The monsters and characters, for the most part, were backgrounded by dark dungeons or caverns. Yes, "dark" was the operative word. These were dank, dark, nasty places where only the foolhardy ventured. Unlike the default dungeons of 4E which are (were?) lit, old school dungeons celebrated the absence of light. Those sinister eyes always seemed to be following you through the dungeon from the safe confines of the darkness. So, the depiction of old school dungeons highlighted the play of light and shade. This was absolutely central to providing a sense of drama and atmosphere. It's a shame the people in charge at WotC don't seem to consider this aspect of the game's history in the same way. As far as I'm concerned, they've rejected their inheritance (see Edmund Burke on the French Revolution).
Of course, we all know where the WotC art has taken the game. Rather than an emphasis on monsters, the emphasis, by and large, rests with heroic characters in lit environments. How heroic would it be to hold the torch? The humour, by and large, is gone. The game is supposed to be fun and the art should reflect that IMHO.
Like Sean mentioned in the comments of a previous post, I don't believe the art of the editions can be reconciled. The art must reflect the mechanics, if it doesn't there will be a serious disconnect with the game. Schindehette may not want to here about THACO, but what about all the other mechanics that factor into how a game is played and communicated through art to its players? I think his comment was a little hasty. The art must fit the expectations of the subculture it's intended for - if it doesn't you won't reach your audience and people won't find the game meaningful. I'm not saying they should go whole-hog with old school art (although I wouldn't mind), but they're going to need to make very difficult decisions indeed. I have no doubt of this: the art of 5e will tell you a great deal about the target audience.
I'd like to say that I'm wrong in my outlook, but I don't think I am. I am willing to stand corrected, but the WotC Creative Team will literally have to pull a white rabbit out of Pinto's Conical Cap - and I just don't see it happening.