Speaking for myself, 4e is when D&D finally fulfilled the promises it had been making to me since 1982.
This is true for me too.
The Foreword to Moldvay Basic, with the slaying of the dragon tyrant with a sword gifted by a mysterious cleric, was what I was looking for.
Oriental Adventures, in 1986, was the first version of D&D where I started to work out, as a GM, how to achieve it (eg focused PC design, rules for backgrounds, a default backstory that integrated those PC backgrounds, etc). But for me 4e took D&D to new levels.
if you follow the progress of D&D, 4e sticks out. It alone will be a special snowflake in terms of world, mechanics, tone, and design.
I tend to think that this is somewhat in the eye of the beholder, and perhaps depends on what parts of D&D's progress have been most salient to any given player.
For me, 4e emphasises and really develops parts of D&D mechanics that were always there - classes, levels, hit points, non-simulationist saving throws, etc - whereas 3E seems that it's trying to turn D&D into something it's not (a would-be process simulation still saddled with classes, levels and hit point).
The first set of books give very little cogent advice or direction on how to effectively use the mechanics beyond setting up AWESOME! encounters. I personally didn't even see it as all that much of a mechanical evolution and totally whiffed on running it "indie" style.
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When I came here after the 5e announcement, I was flabbergasted by the way folks like you and pemerton described your games. (Still am, to some extent.)
My suspicion is Manbearcat and pemerton fell into a mode of play the designers didn't understand existed in their game. I certainly never saw strong indie advice or any offerings of that sort of play in any published material produced by WotC
I'm always happy to be a crazed and daring trailblazer, but on this occasion I feel I was just following the lead of the designers.
Worlds & Monsters, for instance, talked about re-presenting and in some cases "re-concepting" D&D monsters, D&D gods and similar story elements to make them speak more to actual play. That is, to me, a very "indie" sentiment. And when skill challenges were first
previewed on the WotC site, they were clearly an attempt at a scene-resolution mechanic of the sort found in games like Maelstrom Storytelling or HeroWars/Quest. (And, with their back-and-forth between GM framing and players rolling all the dice I think they have strengths that not all forms of such mechanic have, even if they have weaknesses as well.)
Contrary to what's being said in this thread, there were plenty of other comments and previews in the period leading up to release (see for instance
this index on the WotC site). And to me, at least, they made it clear that the game aimed to
use the mechanics in classic indie fashion - rather than ignoring the dice to tell a story (which is the classic 2nd ed AD&D/White Wolf "golden rule" approach), the game was being designed so that
using the mechanics would produce classic D&D stories. This was what Worlds & Monsters spoke about, and what those previews spoke about too.
And Rob Heinsoo himself, in a pre-release interview, made the
comparison to indie games:
There might not be anyone else out there who would publish this kind of game. They usually get entrenched in the simulation aspect.
Indie games are similar in that they emphasize the gameplay aspect, but they’re super-focused, like a narrow laser. D&D has to be more general to accommodate a wide range of play.
That interview was given on March 5 2008. Between it, and Worlds & Monsters (I didn't look much at Races & Classes which seems a lot less interesting), plus the previews on their website, I wasn't surprised at all by how 4e turned out - except that it was even better than I had hoped!
I think those who were shocked, upon release, perhaps hadn't really taken the designers at their word, or hadn't fully appreciated that they really were setting out to build an RPG where using the action resolution mechanics is not some sort of supplement to playing the game, but
is playing the game.