My pick isn't a current game. In fact, it came out over 35 years ago. And yet, for me, the artwork on this box and its red book captures the essence of the game better than anything else before or since. There's been a lot of talk around "weird fantasy" in the OSR community the past few years and what that term means. Erol Otus' beautiful, evocative painting epitomizes that mix of sword & sorcery with strange otherness that perfectly defines the original, weird flavor of D&D. It's a vision I've chased ever since and I'm willing to bet I'm not alone. I think a good deal of the nostalgia and romanticism of the OSR can be found directly in this image. The eerie, magenta dungeon, the subterranean dragon, and the two bold adventures may not actually represent your typical D&D game, but in my opinion it is suffuse with the spirit of the game.
My honorable mention might go to the cover of Frank Mentzer's Basic red box. Again, it's so immediately associated with the game, a touchstone for so many like myself playing in the 80s. It, too, is such a great, iconic cover. Artwork for most modern games typically don't inspire me with their heavily-muscled superhero bodies. Either way, we can all agree that a PDF can't do a great cover justice like a physical book or box can.
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