TSR On the Relative Merits of the TSR Editions

So, because I'm a completist, I actually read through (okay, skimmed) the entire thread before typing this.
I don't know what kind of grognard I am, but I've been playing this game since we had to color our pale-blue math rocks with crayons. My first exposure to D&D was either White Box or Holmes - OD&D rules, at a friend's house when I was a precocious child of, I think, 7.

That Christmas (1980), we got a copy of the Tom Moldvay Basic Set. I distinctly remember making our first characters with the help of an older family friend who was a wise older girl of 13. Not long after, we got a Monster Manual, PHB and DMG, and Cook Expert set . And then all the rest. I still have EVERYTHING but my original PHB which got destroyed, or stolen, or lost. An orange-spine edition replaced it.

I think I've said it before, but like many people I played a hodgepodge of 1e and B/X. We used AD&D class/race combos and alignment, but relied on B/X for a lot of the rules questions. I got an AD&D fighting wheel that I continued using right up until 2e. And here is my impression of the best parts of the editions I had, with the perspective of years:

Hands down, the best entry point to D&D for new players goes to the 1983 Mentzer Red Box. It was evocative, descriptive, and essentially introduced roleplaying games as "Choose Your Own Adventure" novella with a randomizer. Just brilliant.

1e had a LOT. But the organization was terrible. So for me, that was a whole lot of using the rules I liked and chucking the ones I didn't.

I could run 2e NOW. I might muck up a spell effect or two, or count slots wrong, but I'd been using proficiencies for years by the time it came out, and like a lot of folks, I don't know that I did much other than use new books (fewer things to look up) and occasionally get mechanics wrong. 2nd-Edition also gets honorable mention for the game's second best descriptive intro explanation ever - the "Chutes and Ladders" analogy. It's not quite the Red Box's walk-through adventure, but it's not bad at all.

I liked some of the 2e player's option stuff, especially "Channeling" in Player's Option: Spells & Powers.

It's actually somewhat mystifying to me that TSR never quite figured out how to "do skills" well in D&D. There were so many fiddly subsystems for "I attempt X," that it's mind-boggling that nobody there tumbled to "Hey, why not use the same d20 we use for the most common resolution we do in the game - combat?"

I could do a long rant about how what I wanted 3e to be a mechanically cleaned up 2e, and instead what I got was a much more "over the top" fantasy setting. It was the first time I felt D&D had started overtly embracing what I can only describe as "high-magic fantasy superheroes."

And for all that I like the cleaned up mechanics (and better presentation) of some more modern games, the aesthetics of them turn me off.
 

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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?
I will most definitely go with AD&D 2nd edition. I think the three core books were $18 each, so with a $15 weekly allowance, it didn't take me long to purchase all three. It wasn't the first RPG I ever bought, but it was the first edition of AD&D I ever purchased with my own money (not counting The Keep on the Borderlands). I also owned quite a bit settings, adventures, and other supplements for the game. I played AD&D 2nd edition from 1989 until around 1997-98, so 8 or 9 years. I've played D&D 5th edition since 2014, but I've clocked more hours with 2nd edition than I'm likely to get with 5th edition.

I can't speak much to my preferred playstyle on the grounds that it was such a long time ago. While I have happy memories of AD&D 2nd edition, wild owlbears couldn't get me to play it again.
 

1e. No, 2e. No, 1e. Can't decide.

Actually I started in the early 80s with the BX red box and played a lot more BX/BECMI than 1e, but these days we play 1e (not that I get to play much...).
 
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