Vintage gaming community.
Rules:
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X-Com - UFO Defense and Terror from the Deep (I remember hacking my demo copy of UFO Defense and bypassing the shareware check. Still my all time favorite strategy game)
Doom
Duke Nukem 1, 2, and 3D
Wolfenstein 3D
Jetpack
Commander Keen
Raptor: Call of the Shadows
Rise of the Triad
Monster Bash (Just pretty much anything 3D Realms or Apogee related was gold)
Moraff's Dungeons of the Unforgiven(Only ever had the shareware version as a kid, but I played it over and over)
Fate of Atlantis is pretty good
SSI gold box D&D titles and Dungeon master, though both are better on Amiga
Myth The Fallen Lords and Myth 2 on the Macintosh. This was my favorite multiplayer game I’ve ever played by far.
Other great Mac games from my youth: The Odyssey (1994) by David Larkin Sim City and Sim City 2000 Rogue Sim Ant Prince of Persia The Scarab of Ra Realmz Path Ways into Darkness and Marathon
And my favorites on BBS were Major Mud and Legend of the Red Dragon.
I didn't have a PC, but when I went to friend’s houses I would play the shit out of Doom.
C64: Elite. the game is my personal number one as I played only Elite constantly for a long time, despite all other games available for C64.
Amiga: Chaos Engine, Transarctica.
486: Elite Frontier, Descent, Descent II.
Xwing, day of the tentacle, Sam and Max hit the road, terminal velocity, half-life, journeyman project, Myst, that weird Encarta cdrom trivia game, counterstrike, EverQuest, you don't know Jack, Spiderman cartoon maker, master of Orion, monkey Island, Commander keen, and DOOM
Lode Runner for Apple II. Still remarkably playable. You could also go for The Legend Returns on PlayStation / Saturn.
Oh, yes. And you could make your own levels!
Carmageddon is a game that I loved at the time, and am very hesitant to revisit... I suspect it hasn't aged well!
Ocarina of time Red Alert .. yeah probably just those two would do me
Amiga:
ZX Spectrum:
Myst and Obsidian
Lords of the Realm 2, the OG X-Com trilogy, Total Annihilation, Dark Reign, Civ II Test of Time
Squarez Deluxe (which is now Freeware!)
It's a thinking man's Tetris and about 100x more rewarding to play
amiga wings of fury
atari 1040ST outrun (the audio on atari!!!)
c64 zak mckraken
There was this older 90's (I think?) game I loved but I can't figure out the name or find it, despite some googling. You played the part of someone piloting a drone on a space station that had a viral outbreak. The virus alerted the DNA of the victims that the automated security system could no longer identify them as friendlies and so went on a killing spree. You're trying to find video clips from the inhabitants, collecting DNA samples, very point and click adventure with neat animated scenes with FMV. If this rings a bell or if anyone knows it, let me know!
Baldur's Gate
Lords of the Realm 2
Descent (1, 2, and 3)
Sim City 2000
Half Life. While I am too young to have played it when it released, it still was an astounding game for its time.
Obligatory shout-out for any Bullfrog games of that era, especially Dungeon Keeper 1 & 2. Lionhead's Black & White is 1 year out of your window, but such a good game.
Also:
Syndicate Wars
Command & Conquer: Red Alert
Grim Fandango
Rollercoaster Tycoon
Descent
Grand Theft Auto
...I'm in my late forties, so pre-2000 was my peak gaming time. As a result the list could go on and on and on....
OP said pre-2000, Starcraft wasn't released until....
checks Wikipedia
Damn.
Some of my favorites in a variety of genre:
Also one of Sierra's adventure games. A popular one is King's Quest VI.
Late and I cannot possibly read everything here, but I'll come back to it as well.
And just to do some due diligence:
Very space- and RTS-themed, but that's what got my attention at the time. And they were having their golden age. Also I was very young in the 90s, so that's all I have.
The dig. The game is inspired by an idea originally created for Steven Spielberg's Amazing Stories series.
I was a fan of Midtown madness, both 1 and 2.
I had LAN parties with my friends by booting the game, then ejecting the CD and passing it along.
Sadly the third one wasn't on PC.
Tie-fighter was a good one.
And StarCraft like someone mentioned and Warcraft.
My top of the pops are:
Honorable mentions:
Rollercoaster Tycoon is an obvious must-play. And Zeus: Master of Olympus came out in 2000 but runs on Windows 95. It's a Sierra city builder, and I have thousands of hours in it.
Anything by Blizzard
Anything by id
Most things by Maxis
Half Life
Deus Ex bends the rule a bit, being 2000, but I can't not mention it
Maniac Mansion. I never got far, but it's a silly little point and click game.
*your
Doom (1 then 2)
Dune 2
Command & conquer: Red alert
Quake 2 & 3
Unreal tournament
Rise of the triad
Heretic
Hexen
Space Quest 4
Quest for Glory series
Simcity 2000
Leisure Suit Larry 6
Grand Theft Auto (top down)
Commander Keen in Goodbye, Galaxy. I still own this series on steam and play it when I get nostalgic.
Command and Conquer: Tiberium Sun
Tomb Raider
Mortal Kombat 3
Streets of Rage
Metal Gear Solid
Duke Nukem 3D
Metal Slug
Definitely go and find Marathon and it's sequels, preferably in their original form on the Mac. But you don't need to go through all that trouble necessarily, Bungie released all the source some time ago and it is all freely available for new hardware now.
Total Annihilation. It was released in 1997 and brought inspiration to games like Supreme Commander and Planetary Annihilation.
Also, mother fuckin' Cap'N Crunch's Crunchling Adventure. I don't have to explain that one.