Why didn’t I try AudioScrobbler sooner? It’s a simple plugin for WinAmp/iTunes/Insertyourmediaplayerhere that tracks which songs/artists you play, and how often. No ratings, no genres, nothing you need to be as anal retentive as a librarian in order to track. It uploads this data to a Website, where your listening data is compared with other people’s to find those with similar taste.

You can then use their profiles to discover music you might like. You can even go to their new sister site, last.fm, to listen to a personalized radio station. (Right now I’m listening to a groovin’ downtempo/rap song I might never have discovered otherwise. Because it’s in French.)