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Personally, I'd have to say on the Apple IIe, playing Sun Tzu's Ancient Art of War. I had absolutely no clue what I was doing, but I did realize moving around little pixel dudes on a map to shoot and stab other little pixel dudes was a massively fascinating exercise and that I wanted more. Games, not exercise.
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I had a genesis and atari before that, but it was the first game to really suck me in. For example, I fell out of my chair once trying to pull up so hard on the joystick when I was barreling towards the ground in my plane.
Also Myst is up there on the list, only game where I kept my own journal and it was a really challenging game to beat when I was 10 or so.
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