The first vid I ever saw was an Utena vid to Natalie Imbruglia's "Torn" which holy crap actually still seems to be online. So that was in 1999. I think I just found a random link online and spent two days downloading it.

After that, I watched a lot of AMVs in college via the anime club, mostly on people's VHS tapes IIRC. I think they got the vids via con AMV awards. I saw a LOT of Evangelion vids. The one I remember most is Kevin Caldwell's Engel, as well as Tainted Donuts (Trigun/Cowboy Bebop crossover), Right Now Someone Is Reading This Title (multi, meta), a ton of stuff from ErMaC Studios, Brad DeMoss' Star Wars Episode I trailer redone with Evangelion footage (can't find link), and Kusoyaro's Bachelorette (Utena movie). Some of these were downloaded off my college ethernet connection, and there was a lot of wrangling with codecs, as it was pre-VLC.

The first Western media fandom vids I saw were Buffy vids around 2002-2003. The ones I remember are Strange Disease, Eunice and Myrtle's Fragile, heresluck's Come On and Superstar, and Morgaine's She Bangs. I also remember lurking at We Band of Buggered and watching the vid camp stuff that Valerie set up. Pretty much all the recs I got through my flist on LJ, and that's when I found out about VVC and the whole chronology of media fandom vids from the Star Trek stuff. I had a hard time getting used to media fandom vids at first, because they look less flashy than AMVs, but then I learned more about the aesthetics while lurking in vid camp and stuff.