Because even a reformed nerd needs to flex his pocket protector sometime.
1) F-Zero, Super NES: more sway factor (you know, when you lean right because you think it'll make your car/character/plane go right too) than any other game before or since. And really good music. And because it was the first thing I was better at than my brother.
2) 007:Goldeneye, Nintendo 64: The best multiplayer game, ever. Brilliant (for the time) graphics, sublime sound, terrific gameplay with one player or four, and the unforgettable yelling of, "UNCLE BENNY!!!"
3) Fallout/Fallout 2, Windows: The only time in my life I ever shut myself in my room for two weeks because I couldn't turn off the damn computer. Bad graphics, slightly repetitive combat, but a brilliant storyline and hilarious conversations with in-game characters.
4) Metroid Prime, Gamecube: The only game that ever actually scared me.
5) John Madden Football/Madden NFL, Super NES to PS2: Great games, one and all, and maybe one day they'll figure out how to make the flanker streak less unstoppable.
6) Destruction Derby, PS: my first glimpse at the future (back then) of video games. The game itself wasn't that much to write home about, but fun for about an hour.
7) Joe Montana Football, Sega Genesis: The only reason I'm such an awesome fantasy football manager, because if it wasn't for this game I still wouldn't understand football.
8) Grand Theft Auto 3, PS2: A million tiny games rolled up into one big one, absolutely seamlessly. Vice City and San Andreas are better, obviously, but this one was a giant leap forward over anything else.
9) Elite, BBC Micro and a dozen other systems since about 1985: None of you will ever have heard of this, but it was a truly awesome game. You flew around a galaxy bigger than any game environment you'll ever see, even today. The GTA of its day.
10) Killer Instinct, Super NES/Arcade: I used to stand around in front of this game after running out of coins to play it in the arcade dreaming about having a Killer Instinct arcade machine in my house. When it came out on the Super NES I think I cried.