This is an interesting question because of the purpose of the art in an RPG - it's supposed to help design the world, set the stage, evoke the setting, and bring you into play. And I'm not sure a lot of them do that.
I'm gonna make a couple of off beat suggestions, but remember, again, old.
V&V 2E: I've commented on the art for this before, and but the advantage of having one of the game designers also being a top not RPG artist of the time, and having them be the sole artist on the book, gave everything a unified feel. All of the characters shown are well designed, some are downright iconic (Darkstorm and Gauntlet just look GREAT and could easily have been heroes of their own 1970s-80's comics). The back cover art with the author talking to the players about game play is just so full of energy.
Last one - Vampire: the Masquerade 2E. Man was that stuff mood setting. Just wonderful work.
For 1EAD&D it could be the shenanigans the DM could be getting up to. although maybe not as adversarial as some of Gary's Writing.
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