For me, it was the game Rocket Jockey released by Sega Soft in '96. It was perfect. The game featured a surf rock soundtrack by Dick Dale. The entire premise of the game was to ride around on rockets and using long cables to yank your opponents off theirs. Referees were also fair play. I don’t think I’ve met anyone else who has played the game, so if you have, let me know!
The Moraff adventure games. Moraffs World and Moraffs Dungeons of the Unforgiven.
Also Castle of the Winds.
It’s either tough or impossible to get purchased copies of any of them now, but that means there are sites willing to host the full unlocked versions of them now. As far as I know, the creators of both are still alive though. So I suppose if you tried really hard you might still be able to get money to them.
In both cases they were games I played when I was a kid and they stood out as games I wanted to come back to when I was less bad at stuff. And in both cases I did, and little me was right.
I recently played through Castle of the Winds again, works great in DOSbox with Win98. Still a great game.
I remember the death messages of Castle of the Winds: RIP Killed by Huge Ogre or RIP Killed by Kobold. I had never seen or heard of an Ogre before and thought it was “org” so I pronounced it that way too for the longest time. Until Shrek was released.
I vaguely remember the death message said “another one bites the dust” and I had no idea what that meant.
I played one of the Moraff games (I think Dungeons of the Unforgiven) and remember it being like an acid trip. In retrospect I probably didn’t have the colors set up right.