Mental Omega, a total conversion mod for Red Alert 2, Yuri's Revenge.
Age of Empires 2.
Settlers II is the one I go back to from time to time (though nowadays I'm playing the "History" version on uPlay). And of course, all those old Lucasfilm/-arts and Sierra games.
Also there was this 3D-ish platformer called Sky Roads I used to play a lot back in the day. But I haven't played that in ages. I don't even know who developed it.
Oh, and Wing Commander 3 and 4. Both really good games.
FX Fighter, Enemy Engaged: RAH-66 Comanche vs. KA-52 Hokum, Sim City 3000, Descent, and Carnivores 2. Just love the janky 3D, complicated keyboard bindings, goofy UIs, and crunchy textures.
For me personally, that has to be Broken Sword 1 and 2. There’s always been something about those games that keep me coming back on yearly basis - there’s few games that can do that for me.
So there's this old DOS game called 'Archipelagos'. You just wandered around this weird checkered liminal space looking for obelisks. I dont remember much more than that but it was just such a weird and different game and I loved it.
Lords of the Realm 2 - I still come back to it regularly. Holds up pretty well (though battles were kinda easy to cheese).
Digger.
I found a Win version the other day... and it still kicks my ass - just like it did when I was thirteen.
Vintage gaming community.
Rules:
If you see these please report them.