http://www.pandora.com
It's streaming internet radio, perfectly legal (they pay royalties and are ad-supported, but only side-bar ads, never obtrusive). The cool thing is anyone can make a "channel". You basically log in, and tell it something you like, be it a genre, an artist, a song, or lots of all 3, or just a list of bands, or whatever, and it'll start playing things that are similar music to what you tell it. You can then rate each song that it plays, as a "Like" or "Dislike". Based on that, it'll continuously change the profile of that channel and learn better what you like and dislike. And you can make lots of channels, one for whatever modd you're in. Also, you can browse through other channels that other people have customized and listen to them, or make that channel on of your own and then tweak it yourself.
For instance, I'm usually in a classic rock mood, so I went and found a classic rock channel that someone created. It was almost perfect, but he had made it so a little too much older music played, a little too much Elvis for me too. So I tweaked it slightly with a couple of dislikes and a few likes, and it fits me perfectly. So, most every song it plays, I like, even when half of the songs may be ones I've never heard before. If there's one I really like, I can go buy it on iTunes or whatever. It's great.
That sounds like what they want to do with that thing with iTunes, and it may work well or it may not. Definitely sounds like Apple could be doing more with your data and such, such as creating lists and selling them. If you try it, I'd DEFINITELY read their privacy policy and the terms of use with the program.