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Mental Omega, a total conversion mod for Red Alert 2, Yuri's Revenge.
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Age of Empires 2.
RetroGaming
Vintage gaming community.
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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.
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.
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.
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.