Okay, here's mine:
My oldest video game system was an Atari 2600. My parents got it and I only had a few games for it.
My first real system was an NES, which I got in 1990 for my 9th birthday. My first games were Super Mario Bros./Duck Hunt/World Class Track Meet and Mega Man 2. It is the only system that I got that no longer works.
In Christmas of that year, my mother got my brother and me a Game Boy. Our first games (which started as a joke) were DuckTales, Batman, Tetris, and Super Mario Land.
In 1991, my mother got me and my brother a Super Nintendo. The first game we got was Super Mario World.
In 1993, my brother got a Sega Genesis for his birthday. The first games (one was a pack-in game, the other two we rented) were Sonic the Hedgehog 2, Taz-Mania and Michael Jackson's Moonwalker.
In 1994, my brother got a Game Gear for Christmas. Our first (and only) two games we got for it were The Lion King and Mighty Morphin Power Rangers.
In 1996, my brother and I pooled our money together to buy a Nintendo 64. The first game we had was Super Mario 64. In 2001, I upgraded to a Pikachu N64.
In 1998, my parents got my brother and me a Sony PlayStation for Christmas. Our first game was Final Fantasy VII, but we never played it (neither of us like RPGs that much) so we rented Street Fighter Collection, Parappa the Rapper and Space Jam.
In 1999, my brother got a Sega Dreamcast for his birthday. We never owned any games for it and it pretty much sat around collecting dust.
In 2000, I upgraded my Game Boy to a Game Boy Color (I still own my original Game Boy, but I don't use it). My first game for it was Pokemon Blue.
In 2001, my parents got me a Nintendo Gamecube for Christmas. My first games for it were Star Wars: Rogue Squadron 2 and Wave Race: Blue Storm.
In 2004, I sold my PlayStation 1 for a Sony PlayStation 2. My first games for it were Kingdom Hearts and Grand Theft Auto: Vice City.
In 2005, I bought a used Game Boy Advance. My first game for it was Lilo and Stitch 2: Hamsterviel Havoc.
Soon, I want to upgrade to a Nintendo Wii. I'm a bit of a Nintendo loyalist; I've owned almost every system Nintendo has made except the Virtual Boy and the Nintendo DS. Sony is good too. I don't trust Microsoft and I think Sega is better off making software than hardware.