Jack Daniel
Legend
The best thing about each edition, eh? That's tough.
White Box— The open-endedness of the rules: it's not a game, it's a kit for making a game, and whatever you do with it is all yours. Also, castle encounters! Random knights and wizards and patriarchs on the hex-map that will challenge you to jousting matches or geas/quest your party into doing their dirty work because they can. The original D&D rules imply a seriously weird High Medieval / sword & sorcery / Lost World / Barsoomian setting.
Blue Box— Daggers attack twice per round for 1d6 damage per hit? And great swords attack once every other round for 1d6 damage when they hit? Alrighty then, gimmie a bunch o' them there daggers!
Advanced D&D— That Dungeon Masters Guide. I still maintain that you can't understand how to play any edition of D&D until you've read the 1st edition Dungeon Masters Guide.
Pink Box— So let me get this straight. In this edition, and this edition alone, magic-users can't know more spells of a given spell-level than they can cast in a day, and they can't learn new spells from scrolls or captured spell-books without leveling up first? And this is the OSR's darling edition, the one that all the hipsters and faux-grogs treat as the idealized platonic form of pure, uncut, mainlined D&D? Cool. Cool-cool-cool-cool-cool…
Red Box— If you said that Aleena is the best part about this edition, congratulations, you're a mensch. If you said Bargle, congratulations, you're either a bastard or a Dungeon Master. As if the Elmore art wasn't awesome all on its own, this edition also gives us Gazetteers and Creature Crucibles, so… yeah, this edition pretty much is D&D.
Advanced D&D 2nd Edition— Those leather-cover splats… there's just something ineffable about those. The blue and green ones are top tier, but they're all useful in their own way. If you're very careful about using kits. Also… Caldwell and Easley art. This is where the aesthetic peaked, people.
Black Box— I couldn't tell you which has been more useful to me down through the years, Zanzer Tem's Dungeon or the Rules Cyclopedia. But let's give it to the Cyclopedia because of that iconic Dykstra lineart.
D&D 3rd edition— Well, I do have to admit that I have some nostalgia for the faux-tome core rulebook cover art. Seeing that 3rd edition Player's Handbook on the shelf of a shopping-mall Waldenbooks was a watershed moment, that's for sure. I'm not fond of these rules anymore, but I could still be persuaded to pick up and play a game of core-only 3.0, which isn't something you could say about 3.5, so… best if I end my list right here. The best thing about the edition? No question: Meepo the kobold.
White Box— The open-endedness of the rules: it's not a game, it's a kit for making a game, and whatever you do with it is all yours. Also, castle encounters! Random knights and wizards and patriarchs on the hex-map that will challenge you to jousting matches or geas/quest your party into doing their dirty work because they can. The original D&D rules imply a seriously weird High Medieval / sword & sorcery / Lost World / Barsoomian setting.
Blue Box— Daggers attack twice per round for 1d6 damage per hit? And great swords attack once every other round for 1d6 damage when they hit? Alrighty then, gimmie a bunch o' them there daggers!
Advanced D&D— That Dungeon Masters Guide. I still maintain that you can't understand how to play any edition of D&D until you've read the 1st edition Dungeon Masters Guide.
Pink Box— So let me get this straight. In this edition, and this edition alone, magic-users can't know more spells of a given spell-level than they can cast in a day, and they can't learn new spells from scrolls or captured spell-books without leveling up first? And this is the OSR's darling edition, the one that all the hipsters and faux-grogs treat as the idealized platonic form of pure, uncut, mainlined D&D? Cool. Cool-cool-cool-cool-cool…
Red Box— If you said that Aleena is the best part about this edition, congratulations, you're a mensch. If you said Bargle, congratulations, you're either a bastard or a Dungeon Master. As if the Elmore art wasn't awesome all on its own, this edition also gives us Gazetteers and Creature Crucibles, so… yeah, this edition pretty much is D&D.
Advanced D&D 2nd Edition— Those leather-cover splats… there's just something ineffable about those. The blue and green ones are top tier, but they're all useful in their own way. If you're very careful about using kits. Also… Caldwell and Easley art. This is where the aesthetic peaked, people.
Black Box— I couldn't tell you which has been more useful to me down through the years, Zanzer Tem's Dungeon or the Rules Cyclopedia. But let's give it to the Cyclopedia because of that iconic Dykstra lineart.
D&D 3rd edition— Well, I do have to admit that I have some nostalgia for the faux-tome core rulebook cover art. Seeing that 3rd edition Player's Handbook on the shelf of a shopping-mall Waldenbooks was a watershed moment, that's for sure. I'm not fond of these rules anymore, but I could still be persuaded to pick up and play a game of core-only 3.0, which isn't something you could say about 3.5, so… best if I end my list right here. The best thing about the edition? No question: Meepo the kobold.