A few that come to mind for me:
1. Centurion: Defender of Rome - a turn-based strategy game that came out a year before Civilization. Had some really interesting real-time battle mechanics and as a history nerd I loved taking over the various Roman era countries and kingdoms.
2. No One Lives Forever (and sequel) - a 3D shooter set in an Austin Powers / Archer like universe. So different from other shooters of the time with a great blend of a coherent story, interesting character (named Cate Archer, funny enough), and non-stop hilarity. Gadgets included lipstick camera, coins you can throw as a distraction, and a proximity bomb that looks like a kitten.
3. Acrophobia - a 90s online multiplayer game where you had to turn random acronyms into phrases that had to fit a particular topic. Winner was determined by voting. An amazingly fun time-waster.
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