I've been struggling recently with a desire to get some fresh music into my collection. This is a struggle because of my reluctance to do anything which might encourage the RIAA to continue to alienate their customers and their artists.
iRATE is an application written in Java which downloads music that's available on the web for free download. It allows you to rate music and tailors your downloads to those which match others' with similar taste. So far I've only downloaded 5 songs, but they're of far higher quality than any of the other "free downloads" I've looked at previously.
On a site note:
Also interesting, the application is compiled under Linux using gcj which means although it's written in Java, it runs as a native application!