The Karma is by far the best MP3 player I've used, shame the scroll wheels broke and that Rio went bust before they could release an update.
Really can't remember the first mp3 I downloaded, or even where it was from. I remember using allofmp3 quite a lot, but I think that was later. Mind you, ripping my existing collection kept me occupied for years.
RealPlayer (??) was my first mp3 app, what a piece of absolute crap. Was so happy to ditch that shit and move to WinAmp & whatever AudioGrabber's predecessor was called.