In 2008, Monte Cook shined a little light on the art process down at WotC for DnD 3E:
When I worked at TSR, there was always basically a truism in cover art–the central figure had to be a white male. Most of us actually helping to create the cover art, either by conceiving it or actually creating it, hated that kind of outlook, but the powers that be believed that our audience was entirely white males and they needed someone that they could identify with on the cover. This was absurd for two reasons:
1. You’re talking about a game where you pretend to be elves, halflings, or other things that are different from you, is it so hard to believe that the people who engage in this hobby might be able to see beyond themselves?
2. It’s not only incorrect to assume that the audience is all white males, but it just makes the issue worse when the artwork only fixates on white males. It’s a self-fulfilling prophesy, in other words.
So, when D&D was bought by WotC and we started working on 3E, we really felt that this was a time when we could break this mold.
Sound promising? Don’t get too excited. Just read on, and shake your head sadly. And bear in mind that while this was 3e, and this was a “long time ago” it (a) actually wasn’t that long ago and (b) this nonsense still goes on today, everywhere, all the time.