With the new edition of Dungeons and Dragons, we come to the point of what I hope to be a new "look" to the game. To me, Dungeons and Dragons' editions are represented by the artwork that was presented to me when I learned the system. For me personally, there was the nebulous time where I had 3 different versions of the rules to cypher through. It was when I inherited my cousin's extra book set. In it were modules from 1st Edition, the rulebooks of 2nd Edition, and then I had my own set of "Basic Dungeons and Dragons". The common thread to all of those was oil paintings. In my opinion, the highest era of artistry in D&D was the 80's when the Dragonlance crew was making amazing artwork for the entire line. Here are some examples:
The dragons in these paintings seemed real, and to this day, when I play, this is what I imagine in my head. A sort of realistic style to a fantastic genre. Look at the character designs. They are rooted in what people would actually wear. There is some historical accuracy to the pieces of armor, the clothing being worn. Things seem to make sense(except for female armor, but at least its not metal bikinis).
When 3rd came out, I loved the artwork. As you can see in the examples below, the team went a little bit JRPG/Comic style. Characters wore stylish armors with buckles, straps and bags everywhere. The weapons were very much not rooted in reality, being overly large and bombastic. It was a huge change from what 2E was presented in the Revised edition(black books), which was encyclopedic and not very exciting.

But that's 15 years of the same style, through technically 4 editions of the game(3rd, 3.5, 4th and Pathfinder). While great, I think a change in art style really shows a fresh new start, something 5th Edition D&D desperately needs. Here's some of the cover art.


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