I recently worked my way through the old games library on archive.org and found some gems I used to play.
The game that got me looking there in the first place was Lost Dutchman Mine (still holds up!), but then I just kept scrolling and have bookmarked dozens of games. I won't list them all, but some favourites I grew up playing (and still occasionally revisit) that I don't think were massively (or at least still would be) well known:
Xonix - the first pc game I ever played, back when monitors only had 2 colours lol
Jones in the Fast Lane The Sims if it was a board game
Mario is Missing Yes, the Mario. I was the only person I know to own and play this game
Home alone and Home Alone 2 both on 5¼-inch floppy
Goblins I never got far in this game as a kid, and I have resorted to digging up the walkthrough even today to progress lol

Not a game, there is also Jerry Springer the Opera, a satire which I feel went far too low under the radar, and more people should watch (I think most people assume that the first act - a mock up JS episode, is all it is, but it really isn't). I've listened to it so many times I can literally sing you the whole thing from beginning to end (OST is much better quality than the live recording, and is on YT too). 😂(CW: contains some outdated and offensive terms and slurs)
E: here's a no-spoiler taste, the ad break
Edit again (I'm now re-watching it and this part just came up and reminded me lol): some folks here might be familiar with I Just Wanna Fuckin' Dance, which is from the opera!

There are probably many more, but I've just woken up, so that's all that comes to mind rn..