If you want to play the best version of D&D, I recommend the first-edition AD&D. I use the OSRIC index as a guide and to simplify the rules, much like the OSE books do. If there is something outside these books, the original three books can fill in the missing spots, but I do not miss them.
Also, the first edition is the best-balanced version of the rules. You are not getting all the bells and whistles of the Wizards' implementations, but you do not need them. This is the game Gary Gygax designed, poured his heart into, and perfected. OSRIC has all the patches, clarifications, and fixes. A few parts were eliminated (bards, psionics, monks), but these were for the better.
Also, with OSRIC, I get to play the OSRIC+ game incorporating the BRW Games books. The old ADAD game was terrific, and it is nice that we still have the "added parts" in these books to enjoy and expand our game. You can find the bard in this book; it is a better version.
I don't recommend AD&D 2nd Edition. This is TSR forcing Gary out and bending the knee to the Satanic Panic. It feels like a censored game without the epic battle between gods and demons. It is much more slick and polished, but I feel it loses its heart and soul. If you love this, great, but it feels like so much is lost here. Even though they brought the renamed demons back later, the game embraces escapism rather than feeling like a test of a player's humanity and morals.
I like OSRIC and the BRW books the best. AD&D 2nd is up there (and a worthy choice), but it can never top the original experience of the late seventies to late eighties. The original rules have a raw, primal, gritty feeling, and Gary's writing makes the experience magical, almost spiritual.
OSRIC for the rules.
Original AD&D books for inspirational reading.
Gary's words will inspire you to play something greater than yourself.
The best version of "Wizards D&D" is D&D 3.5E, without Pathfinder 1e's improvements. Staying true keeps Hero Lab compatibility, and it keeps prestige classes as the focus of the game. This version has massive problems; there are broken builds all over the place, cheese tactics, and a considerable margin between optimized and unoptimized characters. Minions can ruin the game. Casters rapidly outpace martial classes. Skill modifiers can become outrageous.
But this is the best of the West Coast designs. Granted, Wizards can never design a game that works past level ten, but having Monte Cook and other legendary designers doing the game design here more than makes up for the MtG-inspired mess that Wizards brings into the fold.
I am not considering Pathfinder 1e since it is a tonal shift away from the D&D design ethos. Pathfinder 1e is more of a game built for adventure paths, and it has a strong Golarion focus and feeling. With D&D 3.5E, campaign sourcebooks, and prestige classes are built for these worlds. If you are playing in Eberron or the Forgotten Realms, play the game supported by the sourcebooks. D&D 3.5E skills feel more "dungeon-focused" than Pathfinder 1e's generic skill list.
D&D 3.5E beats 5E, hands down. The builds are better, the rules are old-school, and the prestige classes give us things to work toward. It is more complicated, but not by much, considering the slog D&D 5E's high-level combat has devolved into, with all the multiple action types, double-casts, resting rules, and general interconnected mess of relationships and rules interrupts.
D&D 3.5E feels more straightforward to play than 5E. So what do we lose, "advantage and disadvantage?" Are we back to modifiers? So? No significant loss, and the A/D system feels so overused these days that it gets tiring. The A/D system is also a hammer for all problems when it is too blunt, a tool that lacks nuance and ways to finesse and modify a roll.
Both of these games are my "peak D&D."
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