Mercurius
Legend
This picture inspired a thought, a hypothesis, if you will.
When I first encountered Wayne Reynolds' art back in the late Aughties, I thought "I love his unique comic-ish styling, but man, I sure wish he'd cut it out with the big swords and the worse excesses of anime-stylings. I mean, how many buckles do you need?" Or something like that.
Meanwhile, when I look at some of the old and simply amateurish art of the D&D I grew up with in the early 80s, it feels classic, or at least pleases my nostalgia sensibilities. I mean, let's be honest: Erol Otus wasn't a very good artist (at least in terms of technique), but he holds a special place in my heart as one of the iconic D&D artists when I first started to play. And don't get me started on the 1E Fiend Folio cover...
I started playing D&D just before the influx of professional artists: Easley, Elmore, Parkinson, Caldwell, etc, who brought an entirely new level of technical proficiency. For those who started much later, it is hard to explain the impact of such art: it was like seeing a technicolor film for the first time.
Here's the thought/hypothesis: back when Wayne Reynolds first appeared on the scene (or I noticed him), I was in my early 30s. If I had first encountered that art back in the early 80s when I was a kid, I might have loved it. But now I'm not so fond of it (or again, I like his technical style, just not a lot of his content).
Or in terms of music, while my tastes have evolved from my adolescence, I still enjoy listening to the Smiths or New Order or The The on occasion, even though there is music that I enjoy more, that resonates more deeply with me, both emotionally and aesthetically (I mean, thank the gods I don't still go to The Cure for emotional succor!).
My point is, we get imprinted at an early age - and the form or aesthetic of something when we first encounter it, holds a special place in our hearts forever. As a general rule. So while I enjoy the art of Erol Otus or Jeff Dee, or that awesome mult-page storybook of dungeoneering near the end of the 1E DMG, I can see why a younger person might think, to quote Luke Skywalker, "What a piece of junk!" They have no reason to be fond of it, because they didn't experience it at the time - it didn't imprint on them.
This doesn't mean we can't acquire a taste for older stuff. I love funk and jazz-funk from the early to mid-70s, and didn't get into it until when I was around 19-20 in the early to mid-90s. It also doesn't mean we can't acquire a taste for newer stuff; I didn't get into hip-hop until my early 20s and downtempo electronica and House music until my mid-20s. And I still occasionally find a newish popular band I like, though my main "locus of taste" is on more obscure stuff.
But my point is, again, that we "imprint" on certain eras, and in a way they become exempt from any refinement in our tastes. They become "classic" to us, while to someone that didn't imprint on them, they seem out-dated or amateurish.