The Half Life Series.
...primarily because me and my mates are always working on mods for it of some sort.
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THE Legacy of Kain: Blood Omen, Portal 2, Minecraft. Those are ever-present. Most of the time I also have Fallouts installed. Though I'm not beating them for the gazillionth time anytime soon, I'm kinda researching canon continuously. A long story.
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Several of 'em. Anachronox, The Binding of Isaac, Super Meat Boy, Deus Ex, Team Fortress 2, and Minecraft are a few of the games that I'll never uninstall. :)
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The Binding of Isaac, Diablo II, Dragon Age Origins, and an old copy of Final Fantasy VII running on a windows 98 virtual machine (since it refuses to run properly on anything newer than that =P)
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Company of Heroes, Crusader Kings II, Dwarf Fortress, Europa Universalis III, Galactic Civilizations II, Garry's Mod, Hearts of Iron III, Hotline Miami, OpenTTD, SimCity 4, TF2, and Victoria II.
At least until Europa Universalis IV and Company of Heroes 2 come out, then I'll probably uninstall EU3 and CoH in favour of their sequels :3
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For me it's Retro City Rampage and Far Cry 2. I don't think I could ever bring my self to uninstall them as they have earned a permanent spot on my hard disk.
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