RetroGaming

• Turrican 1-3 [Amiga]
• Command and Conquer
• Monkey Island 1 [Amiga]
• Sim City 2000 (Network edition)
• Unreal Tournament
• Super Metroid [Super Nintendo]
• Metal Slug [Neo Geo/Arcade]
• Pinball Dreams/Illusions (made by DICE before they renamed themselves)

Speedball 2 Brutal Deluxe and Cannon Fodder are must try (there are both Amiga and dos versions for both).

Lemmings is really good. Original Worms. Lost Vikings. Syndicate.

Killer Instinct

Star Control 2

All challengers can GTFO 🧐

I always go back to the original Age of Empires as a classic.

Wolfenstein and Hover.

Where do I even start ?

• Raw vs Smackdown
• IGI 2
• Freedom Fighter
• KKND

Star Flight

Fairy Tale Adventure

Both from the 80s

Crash Bandicoot 2

Right on Y2K was NFS Porsche Unleashed aka Porsche 2000. As long as you play the PC version it's an amazing game and there are a few graphics enhancing mods too.

Infantry. My first online multiplayer game. Somehow I made it into a squad that got 2nd place in the seasonal tournament and also had arguably the best player in the whole game. I didn't play in the matches but I was in the squad!

Chips Challenge for Windows, Sim City 3000, Age of Empires 2, Super Mario Bros. 3, Command & Conquer Red Alert 2 (Technically not pre-2000 because it was released in 2000.)

Ganja Farmer...

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.

1995ish, Starfighter 3000 - DOS Windows 95

Janky as fuck by today's standards, but that was my gateway drug into PC gaming.

Ore Truck Simulator '96

Septerra Core: Legacy of the Creator

SSI gold box D&D titles and Dungeon master, though both are better on Amiga

Fate of Atlantis is pretty good

Squarez Deluxe (which is now Freeware!)

It's a thinking man's Tetris and about 100x more rewarding to play

Lords of the Realm 2, the OG X-Com trilogy, Total Annihilation, Dark Reign, Civ II Test of Time

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!

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)

amiga wings of fury

atari 1040ST outrun (the audio on atari!!!)

c64 zak mckraken

Boy that is tough. There are a few just after 2000 but I was not doing much in the late nineties. I can't think of anything after xwing series that was not after 2k. Doom2. I honestly cannot remember what I was doing computer game wise in the late 90's.