Pandora
I keep a small stack of CDs on my desk at work so that I can listen to music. No, I don't have an iPod, and no, I don't normally listen to web radio. But my sister's husband mentioned Pandora to me and I decided to check it out. And boy, am I glad I did.
Pandora is a web-radio site based on data from the Music Genome Project, touted as "the most sophisticated taxonomy of musical information ever collected". The idea is simple, but I can only imagine that the execution is exhausting. Rather than falling back on such meaningless labels as "rock" and "pop", the Music Genome Project uses trained analysts to categorize songs based on over 400 different categories based on musical theory. These categories include musical influences, tonality, vocal styles, and melodic progressions, and the result is a truly unique and exhaustive look at what distinguishes one style from another.
Pandora takes this data and leverages it to discover other music you may like. Go to the site and enter the name of a band that you really like. It will start off by playing something from that band. It will then try to select other music that is similar to it. As you go along, you can tell it which songs you like and which ones you don't in order to help it figure out what your taste is all about.