I dunno man. The lacks of pants by the female ranger always bugged me in that picture. What happened to her pants. Did the dragon eat them? I notice that the female fighter's pants are torn. Was that a pants thief but only from females?I think the first work of art I noticed that looked ridiculous to my eyes was an issue of Catwoman way back in 1993 because the gravity defying proportions were just ridiculous. I do have a soft spot for a lot of the old art found in TSR products partly because I prefer the techniques used by the artist but there's a bit of nostalgia there as well. I much prefer Paladin in Hell over a lot of more recent work I acknowledge as technically better. But you're right, stuff that worked 40 years ago won't necessarily work today and vice versa. In 2035, what's acceptable or not acceptable might end up surprising us. Who knows?
Personally, I'll avoid RPGs with over sexualized images on the cover. Admittedly, most of the art from AD&D 2nd edition won't bother me and the image below is one of my favorites. I think the biggest problem with cheesecake in the 80s and 90s is their ubiquity. A lot of young women didn't seem put off by the art in Vampire the Masquerade, some of which was pretty sexy, but I don't recall many instances of art that was just ridiculous. If a vampire woman looked sexy it made sense in the context of the picture whereas in D&D is very often did not.
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