Let's keep striking while I have a moment and the iron is hot. I quoted James Maliszewski's Hesiod-like "ages of D&D" post in describing the "Golden Age" earlier using the 50th tag. I don't personally think that the "Golden Age" is Golden nor do I think that a Hesiod-like descent really applies, but Maliszewski's descriptions, even if his labels are not apt, are still valid. He also oversplits; I don't see any reason to put 1985 or so through 1999 into three distinct ages, but rather one, that did at least have some trends that waxed and waned a bit. Let me start by quoting his descriptions, and then edit them so much that they're essentially unrecognizable, with many additions by me. I'm not noting what I'm editing and adding, so you'll have to read the original if you're so inclined to see what he said in detail. (Note: it's less detail than I'm using even so.)
1985-1999 is an age that marries a sophisticated (some might say "decadent") interpretation of Gygaxian naturalism with a growing concern for "dramatic" coherence. It is one of "fantastic realism" and the construction of believable worlds and stories is its great concern. It's also the age where the Great Wyrm begins to eat its own tail, being influenced not just by epic fantasy generally but more specifically by second or third order epic fantasies that were themselves influenced by D&D. The mass marketing of the game begun in the earlier 80s reaches its fullest flower. In 1983 or so, TSR had released a boxed set that detailed the Greyhawk campaign setting; during this later phase, partially possibly influenced by wanting to replace Greyhawk and stop paying royalties to Gygax as much as possible, this model was expanded on and boxed campaign sets seem to have been a popular item; TSR in fact produced a very large number of campaign boxed sets during this era, especially as the edition rolled over from "1.5" to 2e, and it became a hallmark of the era. Most are exhaustively detailed through many products—a result of the simulationist idea that in order to properly run a game, you needed to know what all of the NPCs and monsters and the weather, climate patterns, etc. were doing independently of the PCs. Even before the boxed sets, the Dungeoneer's Survivalist Guide and the Wilderness Survival Guide expressed this trend by giving you all kinds of details that it's hard to imagine most players were very interested in, like how much warmth a campfire provided, modified by its size and how close you're sitting to it, or how long it took packed food to spoil depending on temperature.
One of the fascinating things about the this period is that it was heavily focused on commenting upon and embellishing the works of the earlier canon. This is very evident in the pages of Dragon from the period, which, if looked at today, would no doubt seem unduly obsessed with minutiae, such as a "realistic" method of calculating a character's height and weight based on his ability scores or determining how far a character could jump up or across based on the same. "Realism" was a watchword of products from this sage. This concern about realism is why issue 88 could, for example, boast not one but two different articles on the physics of falling damage (and a further article on the subject by Gygax himself a few issues later). To some, arguing over whether falling forty feet causes 4d6 damage or 10d6 damage might seem like needless nitpicking and, honestly, it is. This is a consequence of the maturity of D&D. The game had been out for ten years by this point and was so firmly established in its essentials that all that was left to do was gild the lily, so to speak. In short, there's a hint of decadence even amidst the enormous creativity.
D&D also came increasingly to be seen as a generic vehicle for the publication of a wide variety of "fantasy" settings, almost none of which bore much resemblance to the game's literary roots in the earlier phase, and many were indeed detailed as much in a very successful line of extruded fantasy product novels that is another hallmark of this phase of the game. These were less concerned with the game itself frequently, even though written by gamers in many cases, and sometimes the events of the novels had to be shoe-horned awkwardly into the rules to satisfy this perceived need to show verisimilitude.
This didn't just impact the newer rulebooks, but it became a hallmark of the Dragon articles of the time; the "Ecology of..." series being a barometer of the publisher's focus on this kind of fantasy realism. It also crept into the D&D line (as opposed to the AD&D line) and by the time it was retired after the Rules Cyclopedia it wasn't really all that rules lite of a game anymore that still hewed to the original pre-AD&D paradigm of "rulings, not rules" and referee (now called DM) authority. TSR established itself as the authority on how the game was "supposed" to be played and what stuff meant.
Module design had changed considerably too, as I noted earlier, but this wasn't just about moving from site exploration to plotted pseudo-stories—although that did certainly happen. The meme of the "failed novelist module writer" was born in this era as boxed text was first created and then expanded, and in the worst excesses would literally sometimes last for pages. There was a whole lot of expectation of what the PCs would do ingrained here; sometimes literally spelled out in boxed text, but more subtly, the idea that the writers couldn't conceive of the PCs doing anything other than the most liberal busybody "heroic" thing possible was born in this age. I don't know what the politics of employees of TSR was like during the 80s and 90s because we rarely cared about that kind of thing in those days and the internet wasn't around to virtue signal anyway. That said, these all laid the foundation for a great deal of wokeness that was inevitably going to follow eventually, because virtue-signaling morality became a marketing line as 1e rolled over to 2e. Demons and devils were removed from the game, for instance (although they eventually crept back in renamed with funky fantasy names). The garage band feel of the art and presentation had long ago been replaced, by "1.5"'s reprinting of the original books and in anything else that came out, but they still had a kind of edgy Heavy Metal magazine feel to them that was replaced by what—in the case of some artists—literally looked like children's books illustrations. Assassins were also removed as a player class, and a focus on good PR, moral marketing was introduced to the game, much to its detriment. Rather than recognizing that D&D's slight edginess was part of what led to its faddish brief semi-mainstream popularity (the same happened to a lot of metal music genres during the same era; contrary to the beliefs of many of my Gen X cohort peers, metal came as close to mainstream as it was ever going to get because of that perceived edginess, and its popularity faded quickly to a niche. If you like metal, that's fine, but if you just assume that everyone else your age will too, or everyone else who plays D&D or whatever, then you're a victim of perception bias; metal went through a brief period of faddish popularity when Ozzy Osbourne was allegedly biting heads off of bats onstage and bands courted a kind of Satanic edgy look, but when the fad faded, very few people really cared all that much about the music after all.)
Of course, chasing supposed marketing trends is a bad way to do business in most respects, and I have my doubts that people disconnected from the hobby really understand what hobbyists want. (Ryan Dancey's article describing the acquisition of TSR by WotC indeed lays that out as the main factor in TSR's failure.) But that's also part of the story of what happened to D&D in this era. It wasn't just that Gygax was forced out in favor of a non-gamer "generic CEO" figure, although that did happen, but that the direction of the company was pulled away from gamers in general and in favor of a kind of proto C-suite management. This is, of course, considerably worse since WotC was bought by Hasbro, but we're a long way from worrying about that yet... hold tight. Then again, the gamers had also run the company into the ground. At the start of this era, TSR was deeply in debt, and the publication of Unearthed Arcana and the eventually rollover to second edition was largely prompted by the need to generate revenue to cover debts. Gygax had spent the better part of a year in a largely fruitless attempt to get Hollywood to invest in the brand, the only result that I'm aware of being the brief D&D Saturday morning cartoon.
Of course, by the end of the era, most of this had turned to ashes in the hands of these "businesmen" (and women; Lorraine Williams being one of the most prominent figures of the era.) Chasing after marketing trends that never materialized, too much material that cannibalized the sales of each other, and general poor business practices that led to the inability to even capitalize on material that was produced led to TSR eventually in the throes of bankruptcy. Luckily for gamers everywhere, some genuine gamers—who also happened to be successful businessmen, with a juggernaut entertainment company called Wizards of the Coast, but make no mistake; they were gamers first—made it their mandate to save D&D. And they did. In fact, they did so well that the hobby grew tremendously; to levels undreamed of even in the heady days of D&D's faddishness of the 80s. It was still shepherded, sadly, by clueless C-suite woketards, or at least is certainly is today, and lots of decisions made throughout the last 20+ some odd years since WotC was acquired by Hasbro still indicate that they don't really get it, but the gamers who saved D&D made it evergreen, in spite of Hasbro's best efforts.
I don't want to get too into the details of what comes in the next three eras, which tend to be more tightly correlated to specific editions of the game (i.e., 2000-2008 3e, 2009-2013 4e and 2014-present 5e, and soon 6e—although Hasbro is anxious to not call it that) but now not only is D&D a successful brand and successful product, but it is also synonymous to a certain degree with the hobby itself. Loads of people since 2008 or so at least have been playing "D&D" that doesn't even bear the D&D brand name, but which are more similar to older D&D than the current holder of the brand is. While that isn't necessarily great news for the owner of the brand (although they've been making plenty of money and sales of actual D&D are very high), it is great news for the hobby, which probably will remain until the last old grognard finally dies with his books and dice in his hands.
Anyway, although from the very earliest transition into this age, I still think that Larry Elmore and his cohorts are kind of the artistic face of this era. Here's one of my favorites of his, which if I remember correctly, was a module cover art from the Dragonlance series.
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