In my GMing workshops, I mention this Dave Trampier illustration, from the first D&D Dungeon Master's screen:
This illustration was one of the things that made me want to be a GM. I wanted to be the guy behind that screen, the guy telling the stories. There are a lot of pieces of artwork that have impressed me over the years in the hobby, but this was the most formative one.
I'd also include cover artwork by guys like Keith Parkinson, Clyde Caldwell, Jeff Easley, and Larry Elmore in that:
There was also this Jeff Dee cover, from my beloved VILLAINS & VIGILANTES. Pure awesome:
Modern games, of course, have artwork that is of very high quality as a general thing. Here are a couple of modern favourites, from Stephanie Pui-Min Law...
...and one from Blair Reynolds that never fails to thrill:
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