TSR On the Relative Merits of the TSR Editions

OSRIC came out first but Labyrinth Lord took off soon after and publishers embraced it.

I have all the XRP OSRIC stuff but they are pretty much it for support stuff. I have a ton more LL stuff from a variety of publishers.
I definitely saw a ton of support for Labyrinth Lord, including a bunch of stuff from Necromancer/Frog God.

1E stuff is still coming out, though. Two new modules are on Kickstarter right now. And I think once the new edition of OSCRIC fulfills, we're likely to see an uptick in 1E/OSRIC stuff, at least for a bit.
 

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Started with the BECMI boxed sets, moved to 2e when it came out; as a forever DM, originally I only bought the DMG, thinking I could make the game "advanced" only by buying that book...😇
I faced a revolt of my group when I suggested we migrate our campaign to 2e, where Elves could be Thieves!
Anyway...ran the hell out of it (Dragonlance and Ravenloft where our favoured settings, then Dark Sun and Birthright) till 1997 or so, when we started using the PO books (so many toys!)...and our campaign collapsed. I still dislike them (Skills and Powers in particular); so many good ideas, but the implementation left us cold. So much so, that when 3.0 came out in 2000 we embraced it immediately as it promised to be close to 2e+PO, but in a leaner and cleaner package. Overall, we felt 3.0 kept its promise; we kept playing it as we did 2e and BECMI (and kept using a lot of the material of the latter two), so all "optimisation" and munchkinisms and abuses to which the system was prone (as we discovered online later), never surfaced in our games. We also never, ever used any splats for 2e nor 3.0, beyond the setting specific materials.
We skipped 3.5 after trying it (too many needless changes over 3.0 that distanced it from 2e; paladins with pokemon mounts?!), then I moved abroad in 2006 and lost my historic group.

It's been hard to find another stable group, so I mostly skipped 4e, mostly skipped 5e, definitely skipping 5.5 now, fell in love with 13th Age (still hoping to run a full campaign) and ran a few DCC games.
1e has a special place on my bookshelf, as I only acquired the books in 2006, so with the awesome powers of hindsight and experience, I could fully appreciate its virtues without rose-tinted glasses. I would gladly run a campaign with the right group of people.

Now I am preparing a 3.0 Birthright campaign (bare-bones conversion of 2e material) for my kids (which I exposed mostly to BECMI with some forays into DCC and 5e.) If I had to choose a "forever game" now, it would probably be 3.0 (PHB, DMG, MM1/2 only).
 
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I have always (almost exclusively) played multiclass characters, so I've played a lot of Thieves... but it was never really my "primary" class so I didn't get to play with its Kits much, outside of the Swashbuckler.

Played a lot of Assassins, but only when I could use the 1E version or the PHBR15 Ninja.
My first 1e character was an Assassin. I played some Thieves, but they were a class that really took a lot of leveling for their abilities to be viable until 2e's kits came along.
 

So, which edition of TSR D&D do you prefer, for your preferred playstyle, and what kind of game would prompt you to use a different one?
My preferred playstyle is fairly shaped by Moldvay B/X Basic which I mostly learned D&D from to start. As a DM lots of making rulings on what makes sense, even mechanical things like morale and reaction rolls are explicitly optional. Minimal mechanics including only minor attribute bonuses so 3d6 in order and go from there works compared to the incentives for over the top stats in other TSR editions (particularly percentile strength, AD&D reverse bell curve bonuses, and class prerequisites). A focus mechanically on dungeon crawling, wilderness, weird magic, and combat. An emphasis therefore on immersive roleplay and skilled play as a player.

I have had great experiences playing and running AD&D both editions, using elements from BECMI such as weapon mastery in an AD&D campaign I played in, and OD&D has a lot going for it in both the wildness of its tone and the simplicity of a number of its mechanics depending on sourcebooks used.

Playstyle I find works well in most any edition of D&D, whether mechanically stripped down or baroque. I have engaged in my favored playstyle in most every D&D that I have played as a player or a DM.
 

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