Sonic 2 for me. I replayed it, start to finish, multiple times a day, every day, for over a month straight at one point... I don't know whether that's speaking for how good the game is or how stupid I am.
...I'll say it's both.
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Easily my most played of the Sonic games - was thrilled to pieces a few months ago when I got my 3-year-old to play Sonic 2 with me on my iPhone and her iPod Touch (she got to play Tails...)
Now she giggles every time the SE..GA... plays at the beginning, then I crack up and my wife looks at us like we're insane... :)
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That's a tough one. Legend of Zelda Majora's Mask would have to be it for me, but I'm sure I can think of others that are pretty damn close to that level.
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IMO Half Life 1&2.
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