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A few obsessions:
Sonic the Hedgehog 2: I played this game, pratically everyday for about 3 years, though I'd often also go through the whole "story" (Play the first, then the second etc). Probably my earliest obsession, I liked this game just that bit more than the rest.
System Shock 2: I've played it at least once or two times every year since I got it for Christmas in 1999.
Half-Life 1: Similar to the above, except I got it in September for the same year and have played each the Opposing Force expansion pack for the same ammount each year. Oh, and multiplayer, especially in the form of the Science & Industry mod means that I clock up a remarkable ammount of hours each year on a game that is 6 years old... until tommorow perhaps ^^
Homeworld: The whole "I still play it a couple of times through every year" thing.
Deus Ex: The only game I ever got a strategy guide for (and I got it AFTER I completed the game!). Played the demo about 10 times through before buying the game on release day, finding all the different ways to complete the mission.
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