I finally made a tier list of the various versions of D&D. Sure, maybe that's kind of a trendy thing to do; a faddish short-hand when I've already talked at length about this stuff sometimes. But what the heck; I'm not immune to a trendy shorthand when it comes along.
A few caveats; I don't actually love any version of D&D that much. If this were to include some other games, they would be S-tier and no version of D&D would be S-tier. But, I had to rank the versions of D&D against each other, not against something else, so they rank from S to D in comparison to each other. My one S-tier choice is actually a game that I have a lot of problems with... although it's also one that has problems that I know how to fix, because I played it for 16-17 years, and I'd be happy playing it again if I could.
Anyway, I'm not doing this as a video where I rank them as I go, which is the real trendy way to do it, but here's my tier list and my discussion on it.
S-Tier: 3.5. I know that this "devolved" if you will into a charop powergamers game, at least in the perception of those who played it, but if you look at those as roleplaying options rather than powergaming options, the D&D 3.5, especially as played at lower levels and keeping it indefinitely in the "sweet spot" of levels.
A-Tier: Here I put B/X, "the only old system that I'd probably be willing to play", and the Rules Cyclopedia, which is arguably the last iteration of the B/X expression. Albeit with a bunch of higher levels and domain based play, which I'm not terribly interested in. I also put the original 3e; although I was salty for a long time that 3e migrated to 3.5, I did eventually own up to the idea that it is a better iteration of the system (arguably, Pathfinder 1e is yet another improvement, although I'm not 100% sure that I agree with that even now nearly twenty years after the fact.) I could play these, but while doing so, I'd constantly be wondering why I'm not playing a better version of the game instead.
B-Tier: Here we have a bunch of stuff that I think is interesting, but would be less likely to be interested in. Holmes was the first clean-up of the rules and while it is certainly an improvement over OD&D, B/X is a better improvement. I have 2e, which is arguably better than 1e mechanically, but which otherwise has problems in tone that I'd be less interested in. BECMI is fine, I suppose, but I'd be wondering why not just use RC if you wanted to play the BECMI rules. The only thing BECMI has over RC is the sequential rolling out of the rules and the easy to grok writing style. I've also included 5e in this one. It's fine, and I actually do play it. I don't really prefer it or like it, though—it feels, as it would with all of the other games in this tier, that while I'd probably "survive" playing them, I'd always be asking why we aren't playing one of the better tiered versions instead.
C-Tier: If B-Tier are the versions of the game that I would reluctantly accept is someone really wanted to run them, but I'd constantly be irritated with us not playing an A-Tier or S-Tier version instead, C-Tier are the games that I'd probably not even be interested in playing at all. 5.5 doesn't seem like an upgrade to 5e, and the tone is certainly worse. 4e never interested me, except as a source for some setting and fluff material that I'd much rather take out of context and use with some other mechanics enitrely. And 1e is not a game that I've ever really liked. It's too proscriptive, too detailed, too disorganized, and too self-important. Unlike many other people of my generation, I never appreciated the "High Gygaxian" language, and I find even that label pretentious. 1e feels like stream of consciousness writing. 2e is better organized, and if it lost something in terms of charm and edginess, it desperately needed some help otherwise in presentation, writing, organization, and even in terms of the rules themselves.
D-Tier: OD&D has to be at the bottom. It deserves credit for being first, but it is such a mess of organization, poor rules, and poor concepts that it really isn't playable as is without a lot of interpretation covering the blatant gaps in how it's written. I think that carried forward into 1e, because Gygax may well have created the concept of D&D (based on ideas of Arneson, but I think Gygax was better at crystalizing it as a concept) but he isn't a good game designer by any standards that we'd recognize today. Anything he wrote is a hot mess, honestly.
Now, all of these versions probably would require "help." I'd maybe prefer to play Pathfinder 1e + E6 to D&D 3.5, although it's "mostly" the same rules, I guess. I'd prefer Advanced Labyrinth Lord or Basic Fantasy to B/X. So, curiously, my tiers of D&D have to come with the caveat that I think someone else perfected every version of D&D beyond what D&D itself did in its own cycle. Which is maybe a little bit sad, but unlike many of my generation (again; I may be a bit iconoclast) I'm not necessarily nostalgic or sentimental about D&D per se. For much of my participation in the hobby, I've preferred something other than D&D and been unhappy with at least something that D&D did.
But maybe that's also just the consumate homebrewer in me. Nothing that somebody else has created is ever exactly what I wish it would be, so I have to tinker.
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