IMHO:
Pre-AD&D and Basic: Fine, I guess, but I never played, except for running Basic modules in AD&D.
AD&D has the charm of being the fully realized vision of the founder (Gary), full of great stuff, but also disorganized. It was the game with most of the great modules, the “from actual play by the original author” setting in Greyhawk, and made D&D a household name. I learned to play & DM in AD&D, so it’s always the Real Thing to me. I played it for 21 years, DMing for 10.
2nd Edition was basically slightly reorganized AD&D plus stuff I ignored in splatbooks. It was a refinement, but it lost some of the charm of Gary’s game. Conceding to the haters by removing assassins, half-orcs, renaming demons & devils made me mad - as did the expulsion of Gary, rise of Forgotten Realms & uncountable other settings, the destruction of Greyhawk, and much of the art & modules in this era. The result of TSR shutting down sums it up - the meh edition, not terrible, but mismanagement ran it into the ground, and it’s not as lovable, I guess unless you started with it. Played it for 2 years, then moved back to DMing AD&D and other RPG’s.
3rd Edition (including 3.5e & PF) was the Renaissance, the last best version of AD&D. The game was saved from the oblivion of bankruptcy. The team wrote a game that was finally logical and organized, yet true to Gary’s vision in AD&D: default setting back to Greyhawk, original classes and races back, and Fireball and Magic Missile still work like in AD&D. The OGL was genius, saving the game against future bankruptcy and leading to the birth of hundreds of small publishers. The return of the players speaks for itself. It’s not perfect - complicated for beginners and tortured into badness some by power gamers - but it’s truly great. Still my favorite. I’ve DM’d it for 17 years.
4th Edition. I never understood the point. It’s just so different. Short rests? Powers that work lIke spells for Fighters? Fireball and Magic Missile not the same as AD&D? Star Wars cantina of races but no gnomes? I played it 5 years, but I never liked it - I liked hanging out with the group, but the rules were always just in the way of the fun for me. All that stacking of conditions - so not interested - I missed the old days when my paladin could just rush in and swing his sword with “roll a d20”, not play this card with that but only once until the next short rest - if I wanted that, I’d play MtG. A market failure, so I’m the only one who didn’t get it.
5th Edition. I have only played twice, with folks also learning it, so I don’t really know it at all. But it seems like 80% AD&D/2e/3e feel, 10% 4e, 10% new ideas, a great effort at reuniting the fan base after the edition wars. If market success proves whether it’s good or bad, it’s great! I think primarily because, like AD&D, it‘s easy to learn.