All over the place, but none of them too terribly recent:
DOOM/II
Nethack
Master of Orion I/II
Master of Magic
SimCity2000
Tropico
KOTOR
Baulder's Gate II
Arcanum: Of Steamwork and Magika Obscura
Deus Ex
XCOM: UFO Defense (Or: UFO: Enemy Unknown)
Diablo II
Oldest? Probably System Shock 1. I still dig out System Shock Portable now and then. A combined nostalgia and absolute love of the contextual music mixed with the (admittedly very dated) visuals just gives me this sense of emotion, of place, that I just don't get in games today. It's fantastic.
I also regularly go back to play Link to the Past more. It's definitely one of my most-replayed games over the years. It's the only one I have completely memorized. The sights and sounds of LttP pretty much summarize my past to me.
I found a pre-owned boxset of Halflife in a charity shop, the steam code was intact.
It was only supposed to have 4 games but I think the code gave me every HL1 based game.
DooM - I still play this game at least once a week. Even more so since my kids have gotten to age to enjoy it also. My oldest child has been busy making models and maps for the last 4 months for it
ArmA: Cold War Assault (aka Operation Flashpoint Cold War Crisis)
Full Spectrum Warrior: Ten Hammers
Ghost Recon 1
Rainbow Six 3: Raven Shield
SWAT 3
I guess it's pretty easy to tell where my gaming interests primarily lie. I also have Morrowind, Chessmaster 9000, The Oregon Trail (original & deluxe) and Dinopark Tycoon on my notebook. Every so often I'll give Zelda:OOT or MM a run-through, either emulated or on my N64 when I'm home. Also, Starfox 64.
Half Life, Kingdom Hearts 2. Got HL on Steam a long time ago. I actually played through KH 2 on my PS2 back when it was released, but I sold my PS2 when the PS3 came out. I actually re-purchased a PS2, a memory card, a controller, and the game itself just to play it again.
It's become a habit to spontaneously start playing the original Spyro trilogy over and over again. And by playing, I mean completing 120%, or 117% in Year of the Dragon.
Truthfully, I never stop playing games, no matter how old they are. I almost always replay them (which is why I never sell games) after enough time has passed.
Seiken Densetsu 3, Super Bomberman 5, Diablo II, Baldur's Gate II: SoA & ToB, Spyro The Dragon, Dungeon Keeper II, The Legend Of Zelda: The Wind Waker, Frogger, Dig Dug, Liquid Kids, and various older Final Fantasy games.
I still frequently play my old N64 games, namely Banjo Kazooie & Tooie. I'm making my way through Silent Hill 2 and various other Ps2 games. Also I've recently acquired a copy of The Secret of Monkey Island so that's what I'm playing at the moment.
Oh, and I still have soft spot in my heart for Pokemon Blue.
I recently played knights of the old republic several months ago and it still holds up today as the best single player star wars RPG Ive played (not that there are many of those out there). Before skyrim came out I played a bit of Morrowind too.
The one game that I play a lot though is X-Com which is just a fantastic game that I have a ton of fun with. I love being able to run a global anti-alien invasion force and place my bases anywhere as well as getting the equipment of my choice in each base and to each soldier. I can shoot down UFO's, raid landed UFO's, invade alien bases, and even have my own custom base invaded. No playthrough is the same and its just a fantastic game that I can never put down for long
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