Now, what I’m really asking is, who is the greatest pictorial artist. I’m not so concerned with who is the best wordsmith, at least not in this post. And to be fair, I’m not going to decide the matter here either.
There are greats like Moebius, Frazetta, Vallejo, and more. Art is, in general, subjective. Its hard not to pick out people who had a tremendous influence though. Larry Elmore, is one example. Is he the greatest? I don’t know. Did his work for TSR help create an imagery specific to table-top RPGs? Hell yes!
I say this because Elmore was one of the early artists for TSR. Without his art the companies aesthetic would have looked different. Truth be told, not all of his work has aged well. He did a lot of pieces featuring the chain mail bikini trope that probably wouldn’t really be very successful currently. (I chose not to add an example.) Some it represents how people saw the fantasy genre many years ago. Other images though, will likely stand the test of time.
Again, is Elmore the greatest? Probably not. Is Elmore a legend in the world of fantasy imagery? The answer is a resounding yes. He helped put fantasy art on a product that would go mainstream. Without realizing it, there are probably tons of people who link his art with D&D, or even the fantasy genre at large, and they probably don’t even know it. His art was/is good, even if it’s not in line with contemporary tastes. Cheers to Larry Elmore, and his contributions to the world of fantasy art.