Describing the Different D&D Editions

Original Dungeons and Dragons: A loose set of guidelines that allowed fighting men, magic users, clerics, dwarves, halflings, and elves to have unusual dungeon and wilderness adventures.

Basic and Expert Dungeons and Dragons: A clear and focused set of rules that allowed mostly lawful fighters, magic users, clerics, dwarves, halflings, and elves to have fun and easy enough dungeon and wilderness adventures.

Original Advanced Dungeons and Dragons: A somewhat elaborate set of rules, to be interpreted flexibly and sometimes ignored, that allowed a range of classic fantasy characters, heroic or otherwise, to have ass-kicking dungeon, wilderness, and occasionally other kinds of adventures.

2nd Edition Advanced Dungeons and Dragons: A set of rules not so gradually growing from a pretty clear and focused base into something else that will need some wiggle room to actually work that allowed a range of classic, possibly customized, non-offensive fantasy characters to have adventures—including dungeon adventures if you really insist on it—that should be non-offensive and balanced by DM fiat since the style of play being advocated doesn’t really match with the rules; but here are some cool campaign settings and you can still use your older stuff.

3rd Edition Dungeons and Dragons: A set of clear and modular rules that shall be followed and referred to perhaps frequently that allowed a range of sometimes classic highly customized fantasy characters to have detailed and well specified back to the dungeon and other adventures; non-combatable with older editions, but here is a metric ton of supplements, plus three more metric tons from other companies.

4th Edition Dungeons and Dragons: A set of clear and exception based rules that we may need to tweak every few months that allow a range of customized though vaguely similar probably unaligned contemporary fantasy characters to have fun dungeon and other adventures; no, not backwards compatible, no not a bunch of settings, and no, not that much 3rd party support, but check out all these powers and did we mention its fun?!
 

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Going for the one sentence bonus points from the perspective of someone who has enjoyed almost every edition for different reasons...

Original - The original game, 'nuff said.

BX/BECMI - Like Chess, easy to learn, fun and challenging to master.

1st Edition - Classic Adventures.

2nd Edition - Classic Campaign Settings.

3.0/3.5 - The most well defined simulationist style rules, fun to play, DM not so much.

4th Edition - The most well defined gamist style rules, fun to DM, play not so much.
 

OD&D: Awesome. How can it not be awesome if it started this whole awesome thing?

BECM: Awesome. How can it not be awesome with 36 levels of awesomeness?

AD&D: Awesome. How can it not be awesome with boobs in the Monster Manuals? That by itself is awesome.

AD&D2: Awesome. How can it not be awesome with so many boxed sets? Boxed sets are awesome.

D&D3
: Awesome. How can it not be awesome with so much crunchy awesomeness?

D&D4: Awesome. How can it not be awesome when the fighter fights so awesomely?
 
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