I remember using Altavista A LOT. I also remember Audiogalaxy (NEVR 4GET!) and Kazaa with its endless malware and BearShare. Never used Napster, though - didn't have internet back then.
I remember hating RealPlayer (a hatred that will endure even when I'm gone) but mostly using it or WMP for videos. MusicMatch Jukebox was my preferred player for a while, but then I started using Winamp.
Also, for latin american-GAF: I used LATINCHAT when I was bored. It was hilarious and a bit sad... me and my friends, 10 year old kids, using LatinChat and some of its risqué rooms for fun... we could've been easy prey for pedos. Thankfully none of that happened.