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For MMOs: Anarchy Online, when I was invited into the 'BBQ LEETS INC' on RK2. I had the best possible (for my build, of course) imps, armor, I remember I had a perfect PB (this was back before sharks in LE).
It was one of the most prestigious servers in the game, and has been for 6 of the 7 years Anarchy Online has been alive. It has open application now though because the game is really dying down.
That and when we completely finished our city, that was pretty awesome.
It was also really cool to found the guild Anarchy on the Uldum server when the game started out, then after leaving WoW for a few years and coming back to see how huge it was.
For other games:
D2, when I hit 99 in the first ladder season (I came in like 20-something place though).
CS1.6, when I got the invite from my team, due to extraneous circumstances heheh.
A few of my successful strategies in SupCom where I've totally manipulated my opponent throughout the entire game have made me feel pretty good.
I've had some crazy games in both counter strike and UT2004 which have made me feel pretty good.
The most recent though is from GT5:P when I beat a few F2000s (F1 Cars) in my Mines Skyline.
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