My first one was Star Trek TNG: Advanced Holodeck Tutorial for Game Gear. I wasn’t really a trekkie back then (had watched a few of the TOS movies with my dad and liked them but didn’t really care much about Star Trek until around the 30th anniversary I think). I remember thinking the game’s enterprise design was dumb and wanted the stylized one from the movies back (and Kirk and Spock and Scotty instead of these “random stand-ins” :P)

And I think my favorite one was a heavily modded Bridge Commander. I didn’t really play much of the actual game (or “the campaign” as kids call it today) but spent probably around 100 hours playing custom scenarios, battles from the movies and shows.