I’ve been playing D&D off and on since 1979, and I’ve played all the editions. I’ll rank order my favorite editions from a GM perspective. I’ll also comment on the edition from a Player perspective.
My top four favorite D&D games were from the ‘D&D as War’ approach. Things were deadly, scary, and character death was a real possibility. If you encountered an Ancient Red Dragon, you had better run! My least favorite three D&D editions were the 3rd to 5th edition era, all of which approached the genre using a ‘D&D as Sport’ approach where you are expected to have balanced encounters, and monster stat blocks had about 10 times the amount of text and creature special features of the early edition, making things harder to run and slower to play.
1. B/X D&D
B/X is the ‘Basic / Expert’ box sets that were published in the 1980s. It is my favorite edition of the game. Everyone that I knew that played AD&D basically were using some version of B/X for the core rules, just pulling in AD&D classes and monsters. So technically we said we were playing AD&D, but we played it fast and loose. What I like about B/X D&D is that it leaves ample room for GM fiat and ‘rulings, not rules’. It also is very amenable to procedurally rolling up encounters on the fly. These days I would choose ‘Old-School Essentials: Advanced Fantasy’ retroclone, which pulls in all the elements of AD&D (mainly, extra classes, and being able to mix races and classes), which gives me all I really cared about in AD&D. I run a B/X D&D game every Friday for a group of young teens, and the rules are easy enough that they can play it without me having to keep looking over their character sheet or having to manage their character through an online software tool (which seems to be the requirement in some other editions).
I played the Advanced D&D game from 1980-1984 in a twice-a-week game cycle. We probably clocked 3 or 4 thousand hours playing this game. We did run the game fast and loose using a B/X approach, so no weapon speed or other complex rules. Among other things, AD&D has the original Dungeon Masters Guide which is probably the best book ever written to inspire creativity and D&D style adventures. I’d happily run or play this again.
3. AD&D (2nd Edition)
I was busy with college, career, and family during the AD&D 2e years, but I’ve since played it (mainly by Play-by-Post). 2nd edition cleaned some things up, added the notion of ‘kits’ that allowed for more modular character design, and removed references to Demons due to the Satanic Panic era. So it’s very much like 1st edition AD&D.
4. Original D&D (OD&D)
The Original D&D was a brown box but that quickly moved over to a white box, which is what most people called the ‘Original D&D’ rules. It was just three digest-sized booklets. This is the version I was playing in 1979. The rules were a mess, all weapons dealt D6 damage, and the DM had to make rulings to fill in the gaps. But it was wild, glorious fun that was the quintessential style of D&D play.
If you are a dedicated D&D player, you owe it to yourself to at least read these original D&D rules. So much history there. The very first RPG of any kind ever written.
5. D&D 5th Edition
I have run and played this since the first week that D&D Next (the beta version of the game) came out. It is a sort of ‘best parts of all editions’ approach, which did manage to pull together a (at that time) very fractured player base. It is fun to play. As a GM, the game sometimes makes me weary with worrying about encounter balance, and keeping up with the longer stat blocks. It very much follows the 3e and 4e ‘Combat as Sport’ approach, where you go into fights with the notion that it is ‘fair’ and balanced. The fact that you need a D&D Beyond subscription to build and manage characters is (to me) a hassle.
The nail in the coffin (for me) was when WOTC tried to kill the OGL, and was essentially at war with all the 3rd party publishers. The lack of ethics displayed during their posts trying to justify killing the OGL and the bullying they intended to do toward 3rd party publishers was atrocious. They backed off on trying to kill the OGL, but my trust in WOTC is shot, and I will do my best not to support them by buying their new products.
That being said, my original 5e books aren’t going away, and I can still run or play 5e with my friends for years to come.
6. 3rd Edition / Pathfinder
3rd edition was written for a mix-maxer player base that dominated the online bulletin boards in the late 90s. WOTC thought that demographic constituted the majority of players. To their surprise, when 3rd edition came out it very much fractured the player base, since so many (me included) thought it was a very different type of game than the prior editions. This began was became known as the ‘Edition Wars’, with people very much taking sides on which version of these different games they thought was the best.
3e attempted to codify all the rules to make things structured and ‘fair’. If tournament, competitive, graded games were the goal, then yes, this was an interesting game. But its complexity, especially if you included all the splat books that came out about monthly, led you to a point where a harried GM needed to keep track of 1,000’s of pages of rules. The 3.5 edition fixed some rules issues.
But, there were some good things. Ryan Dancy released 3e under the OGL, which forever changed the hobby. When WOTC came out with 4e, Paizo quickly brought Pathfinder to the market, which was sort of a D&D 3.75 edition. Paizo has since released Pathfinder 2.0 which further streamlined rules and provided a more balanced play.
Now, Pathfinder is way more crunchy a game than I would ever run, but I admire Paizo as a company. Also, their organized play adventures are fantastic! Much better than WOTC’s organized play adventures (which have since devolved into a community-driven affair). I would happily play Pathfinder just for their great organized play adventures, but from a GM perspective, I would never run it due to the cognitive burden of having to manage so many rules.
7. 4th Edition
I played it one time. It was a D&D demo game at a local game store. The pregen character sheet I got were several stapled pages. So many feats to keep track of! We got into our first combat, and it lasted nearly two hours. This was all supposed to be a ‘simple’ demo game to get you into the system. I had no interest in such a game, which was really more a balanced wargame with some light RPG elements. I shortly thereafter grabbed a copy of ‘Basic Fantasy’ (sort of a B/X, AD&D retroclone) and ran that for my kids who were just getting into roleplaying.
Now, 13th Age (written by the designers of the 3rd edition and 4th edition) is sort of in the 4th edition space, but in my opinion, is a much better game. It incorporates story elements for more narrative freedom. It has probably the best encounter builder system of any post-AD&D system. I would run 13th Age at lower levels, but at higher levels, I find keeping track of so many feats to be a hassle and distraction.