This illustration, taken from the first interior page of the 1981 D&D Basic Set, is the quintessential D&D image to me.
It has everything you expect from D&D. There's a dwarf, an elf, a wizard, and an archer. They are likely in a dungeon, fighting a dragon.
The fighter is preventing a blast of dragon fire from roasting her companions. The wizard has put two warriors between him and danger, while the archer (maybe a ranger in elven chain?) fires from behind the safety of the fighter's shield.
OK, so the dwarf could be doing something more useful. I like to think that he's a cleric who stepped out of the dragon's way while casting a touch spell on the wyrm. Or, if you don't like dwarves, you can pretend he's clinging to the dragon, begging forgiveness.
Do you have a quintessentially D&D image of your own?
That's a good one. As you can see from my avatar, I'm a fan of David Trampier's immortal works. The quintessential pieces of D&D artwork, for me is Trampier's drawing of a Magic Mouth. The party of dwarves exploring a dungeon, is great.
wrecanAnother good choice is the image on the cover of the G Series of modules: G1: Steading of the Hill Giant Chief, G2: The Glacial Rift of the Frost Giant Jarl, and G3: Hall of the Fire Giant King. They're not the best pieces of art, but they capture the essence of a party fighting together against (literally) enormous odds.
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