I think for me, the special moments are some of the ones that defined me becoming a serious gamer.
One early one I can think of is in Donkey Kong Country 2 for SNES. There's a level about half-way through the game where you're climbing up a pirate ship while the water slowly rises below you, and there's a piranha in the water that will kill you, so you have to move fast. As a very young kid I always struggled with any sort of pressure or anxiety in games -- I was scared of boss fights or any sort of level where something was chasing you, so this was a bad one. But none of my family could pass it either -- no one could even get to the half way point. Finally I was sitting there by myself and I just started going... and going and going. And my anxiety about the level faded and I got all the way to the halfway point, and just kept going and beat it. None of my family could believe it. That was the day I realized I was not only good at games -- I was better at them than my mom and dad. I wasn't better at anything than mom and dad.
Second would be E3 2001 -- I had heard Nintendo had announced the new Gamecube system, and the landmark announcement for me was Super Smash Bros. Melee. I tied up for dial-up Internet line for hours downloading the announcement video and was completely blown away. I've been following all the latest game news and announcements online ever since.
Shadow of the Colossus, 2005. A very impressive, artistic, cinematic achievement for the time, it didn't hit me until the fifth Colossus how incredible this game was. The flying Colossus swoops towards you and you jump on to it's wing -- it lifts off into the air and the orchestra music swells while you rise into the sky, barely hanging on with wind and rain whipping past. It blew me away and re-defined what kind of experiences I could have with video games.
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