
Starcraft - Obviously. What site are we on? =oP It's the first game I modded, and the one I've invested more time into than any other game, ever. Afterall, what other games do you have installed and still play that are over a decade old?
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Monkey Island 2: LeChuck's Revenge - The first computer game I ever played. Its beautiful art style and zany world of pirates drew me in. I was so inspired that I drafted my very first game design: Pirate Island. Yeah, I was young. =o)
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Might & Magic 2 - My first experience with RPGs, and boy did it eat every waking moment I could spare of my younger days. The sound of a party member dying, dun-dun dun-dun-dunn!, still haunts my dreams.
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Marathon - My first experience with FPS games. At the time, my family only had a Mac, so I never played Wolfenstein or Doom until much later. The atmosphere and story of Marathon completely engrossed me. Scary derelict spaceship? Check. Invading slaver aliens? Check. Insane AIs vying for control and manipulating you as a pawn? Check. Dual-wieldable shotguns? Hell fucking yeah, check!
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Half-Life - When my family finally entered the world of PCs, our computer was far from a powerhouse. Still, it could play this, and how I loved it. An instant classic even in its own time. Who could forget the first time they jumped at the high-pitched squeal of a lunging headcrab?
There are a number of other games I'd love to add to this list, such as SimCity 2000, SimAnt, Populous, Starsiege, System Shock 2, and so many others. Five is just never enough. =o)