What is your favorite pre-2000 game? And if it ran on windows 98 or 95 do you still run it?
Master of Orion - still play it today.
Civilization 2.
Still my favorite Civ variant. The game developers definitely had a sense of humor
Else where should our soldiers rest their mighty lances?
I really miss the original Sim City. Ah, the mighty, mighty islands we wrought! When I saw a picture of this I almost fell back on my ass. I hadn’t known those islands were real!
There were a couple of isometric adventure games we all played in the MSX (that “all” is Dad, the Bros and me… Mom didn’t touch computers until fairly recently) that were total timesinks, but I can’t even recall what they were called.
My BFF’s 1-year younger brother had a Spectrum, then a Spectrum 48. He used to let us play with the Spectrum until that day I beat his record at Abu Simbel by a difference it took him months to recover. It’s been over 30 years and his sister still can ruin his day by muttering “Abu Simbel”.
Wing Commander 2.
Doom.
I still play Doom now and then but WC2 is but a memory
Chip’s Challenge - I’d love to install it on my new machines, but I have no floppy drive, so no, I no longer play it.
Picking THE fave is harsh, but among the pre-2000 games I still play on occasion are : *Baldur’s Gate *(the re-release, of course, helped there), the original X-COM, X-COM Apocalypse, Jagged Alliance 2, TIE Fighter, Commandos:Behind Enemy Lines, Fallout 2, Might & Magic VII, *Heroes of Might & Magic 3 *and Thief : The Dark Project.
Came here to post this.
Original X-COM was ground-breaking and seminal. I keep an old Pentium running Windows 98SE pretty much just for that. (And Warcraft: Orcs and Humans. Which also counts for this list.)
X-COM Apocalypse was terribly underrated, but a huge lot of fun. It runs pretty well in DOSBox on a Windows XP Pentium 4 machine I also keep around (mostly for games like this).
*Rise of the Triad *(full edition) if I feel FPS-y and platformy at the same time.
EverQuest 1 was launched in 1999 so it still counts. I hit a really rough patch in life in 2002 and I self-medicated by playing EQ1 up to 120 hours per week. I got over both my RL problems and my MMO addiction eventually but I still have some friends from that era. Tried logging back on later after I had already started playing WoW and I just couldn’t play it any more: the crappy UI and the dated graphics and animations were too much for me. But back in '02 when everything else in my life sucked Norrath was my world of choice.
Doom and Duke Nukem. I fondly recall the last and best sidescrollers like Commander Keen and Duke 1 and 2, too.
I honestly think I played Wastelandlonger than any other game prior to 2000.
Also, the Star Control games, the Wing Commander games, and the X-Wing/TIE Fighter games got a lot of play in college. So did X-COM, Master of Orion 1 and 2, and DOOM.
After college (1997-1999), Fallout 1 and 2 got a lot of play, and so did Ultima Online.
Starcraft is my all-time most played and favorite game. I no longer play it and I barely played Starcraft II when it came out. I’ve grown into a much more casual and less competitive game player as I age.
Hands down it was Sanitarium for originality and creepiness.
Heh, same here, although my junk was Dark Age of Camelot. I got into other MMOs later (often with the same friends I’d made in DAoC), but none just sucked my entire life the way DAoC did. And I don’t say this in a negative sense, either - it probably and quite literally saved my life to be able to lose myself to such extent at the time without the drawbacks of the more traditional ways of doing that.
I never tried it again however, even though IIRC the game’s still got a handful of running servers. Best Frejolfna Nijmansdottir remains a fond albeit fuzzy memory rather than a disappointing fresh one :).
I actually re-logged onto City of Heroes a couple weeks before it closed for good, finding my old, 3-4 years of gameplay-worth 'toon pretty much untouched… and hopelessly underpowered compared to the fresh ones I made and then brought to her level in barely a week :). Thorns/Regen must have gotten nerfed hard in the meantime, because she certainly couldn’t effortlessly wade through group encounters solo any more.
I enjoyed Master of Magic in 1994.
Thanks to https://www.gog.com/ , I can play in in Windows today (and I do!)
Baldur’s Gate, no question
RoadWar 2000.
Wizardry: Proving Grounds of the Mad Overlord.
Ultima IV & Ultima VII.
Doom/Doom 2.
Carmageddon.
Shit, now I’ve got the urge to install DosBox again. 
Doom I & II with the M-16 patch.
Battle Chess.
Sid Meyer’s Alpha Centauri. I prefer it to all the Civs, and still play it once in a while.
TIE Fighter, too, but it’s completely useless under my version of Windows, unless I want to run an emulator. I even have a Thrustmaster stick-and-throttle for it. (As a matter of fact, the vast majority of my older games won’t even install, compatibility mode or otherwise.)
MMO-wise, I still have a bunch of old EQ installers, and played the '99 Project within the last couple of years. Same for WoW, but I haven’t played that in ages. After EQ, City of Heroes was my all-time favorite, until they nerfed the two toons I’d been developing for months (tanker and controller) from near-invulnerability to near-unplayability.