I've recovered my hard drives from 2004, and to refresh myself on the contents of my own desktop, I put my entire Media drive in a Winamp playlist and hit shuffle. Here was a nicely bookended look at how esoteric the shit I collected is:

1) The original Japanese commercial for Chu Chu Rocket (If you've never seen it, find it... it's an experience)
2) James Earl Jones' speech from Field of Dreams: "The one constant through all the years, Ray, has been baseball. America has rolled by like an army of steamrollers. It has been erased like a blackboard, rebuilt and erased again. But baseball has marked the time. This field, this game: it's part of our past, Ray. It reminds us of all that is good and all that will be good again. Oh... people will come, Ray. People will most definitely come."
3) Sumeba Miyako no Cosmos Sou: Suttoko Taisen Dokkoida episode 8: The "little sister fever" parody episode.
4) The Y2K SportsCenter commercial