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Anyone here ever play a Colecovision? My brother had one, I was just a kid, but I remember playing Looping ALL DAAAAAAAYYY LOOOOOONG. :D
Playing Civilization with my friend. The two of us strategizing together, bickering over different policies we wanted to implement. Good times...
Playing Doom 2 over a null modem cable that hung outside the window with my brother and cheating so I could see my brother on the in-game map. Then after a couple of kills he ran upstairs to see if I was cheating, of course I had plenty of time to turn off the cheat.
Hum... There are so many:

My very first fond game-related memory comes from Phantis (on the MSX back in the late 80's) when I was a kid. It was the very first game I've finished and I was very proud of myself:

http://www.youtube.com/watch?v=_fZ5FM7OIq0

Fast forward to the SNES era, I have very, very good memories of Rock and Roll Racing. It was a blast to play that game with friends. We even "teamed up" in pairs to "play against" each other.

Then came the PC era...

Witnessing the C&C cinematics for the first time was mindblowing. I will never forget that intro. Warcraft 2 was also a mindblowing experience to me. The game had a certain "charm" I cannot find in gamesanymore.

Duke3d was another milestone for me. I literally spent nights trying to find the secrets and laughing at Duke's remarks.

Fast forwarding again to what I consider the second gold age of gaming: 1998 - 2001:

Baldur's Gate, Freespace, Half-life, Team Fortress (that came in 1997 but I started playing in 1999), System Shock 2, Homeworld... There are too many to list here so I will describe just one:

Freespace 2. I felt like a actual pilot and a hero playing that game. The game pulled me in so hard I slept thinking about it: Which ship should I use for that hard as nail mission that I could not accomplish the bonus (secret) objetive? Which guns should I bring with me? Also, it was the only game I can remember that made me feel proud of my medals. The feeling I had when I saw that "suitcase" with all the medals is hard to describe. The fact that the game tells you, in the debriefing, by your superiors, that you've earned medal 'x' was immensely gratifying as well.

Fast forwarding to the "present day": Mass Effect.

The intro to the first game left its mark on me. I thought to myself: "This is going to be one of those epic games, isn't it?" I was right. I didn't care at all for the lazy level designs of the side missions or the silly Mako or the stupid mineral gathering. I was so immersed in the game that nothing could break that immersion. Then came Mass Effect 2 and I will never, NEVER, forget that epic ending. I must confess, a manly tear rolled from my left eye as the game ended. A tear of happiness, sadness and pride. Happiness for beating the Collectors (and the game), sadness because I wanted more and the pride for having "saved the galaxy" with all those awesome characters beside me. Mass Effect 3 had some epic moments as well but 2 was the peak for me.

So, there you have it. Some of my fondest game related memories. Hope there's more to come soon.
For those interested, I created a thread like this quite a while back: http://www.gog.com/forum/general/great_or_significant_gaming_memories
playing streets of rage 3 on my sega mega drive with older sister
Finally getting the rotation of my ship right when docking at the space station in Elite for the very first time after many countless crashes!