Have you checked out Pandora yet? (Please don't tell me I am the very LAST person on the planet to figure this one out.) Pandora is a site that pretty much enables you to create your own radio station. Plug in some artists you like, and Pandora will analyze their commonalities and take some educated guesses about what else you might like.
This is a great invention that tempers the scariness of personalized content (soon we will listen only to those voices we have pre-approved, everyone drifting off into their own little bubble-world of one) by constantly offering the thrill of exploration and discovery. Hadn't heard of Garrison Starr until about 16 minutes ago.
Maybe I'm going to have to get an iPod after all.