Looking at the 3.0 PHB, there are only two pieces of art I like. One is the illustration of the druid, which is a pose but contains good "class atmosphere", and the other is of the dragon trying to Swallow Whole on poor Tordek. Other pieces in the book are technically proficient, but these two pieces in particular seem to communicate something worthwhile to me.
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The Tordek picture is good because it implies that Something Can Happen to the PCs. I.e., the PCs are not simply safe uber-powerful beings for whom everything works out well and who are not really in danger after all. Of course, this impression is somewhat ruined by the caption.
The picture of the thief whose Use Magic Device check failed is interesting, too, but for reasons that honestly have very little to do with the game.

In terms of "bad things happening", this one has already happened, and, while surprising, it wasn't really so bad.
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Looking only at the 3e PHB, the illustrations seem to communicate: "You can make a really cool character, who is sort of removed from the world (it is just an out-of-focus backdrop at best), and who will never be in any real danger."
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Mind you, I am not saying that this is
what the game rules deliver, but it is what (to my eye, and IMHO) the artwork seems to say. And this, far more than nostolgia, is what differentiates the artwork.
And I'll also certainly agree that some of the later artwork in WOTC products offers more situation, more mystery, and more danger. Indeed, while the artwork in the 1e DMG and PHB seem to mesh pretty well, the artwork in the 3.0 DMG seems to me at odds with the PHB art. In the DMG, characters can face tough situations. In the PHB, not so much so. This is also problematic to me, because it communicates two opposing views of what the game is going to be like. Again, regardless of what is written, the
artwork is 3.0 seems to communicate mixed messages.
I'd like to see more situational (danger/mystery) artwork that has nothing to do with the Iconic Characters. It seems to me that WotC is starting to move in that direction with projects like the Environment books and more homages to classic illustrations (a very nice homage to the skeleton in the water-filled room trap from the 1e DMG in the 3.0 DMG, btw....while I prefer the original, I was glad to see the piece, and wish the 3.0 PHB had taken more from the 1e version).
Anyway, YMMV and probably does.