It's possible that I'm behind the curve on this one, but I've just recently found out about Pandora Internet Radio. Basically, this site allows you to customize your own user-created "internet radio station" -- if you suggest artists or songs that you like, then the site will play songs from its database that are supposed to be similar to what you suggested. The idea, of course, is that you can discover new (to you) performers with similarities to those you already like.
Having only discovered Pandora this weekend, I haven't spent much time learning all its features, but it looks like over time you can "tweak" your user-created stations by giving either a thumbs up or thumbs down to the different tracks that come up.
I started one customized station based on the band Ween, and two of the tracks that the website chose to play for me were by a guy from Vermont who I'd never heard of before, James Kochalka. The two of his songs that Pandora played for me were "Bad Astronaut" and "Magic Finger". I found them very entertaining. His compositions struck me as funny, tightly crafted, and indicative of an offbeat sense of humour mixing the adult and the childlike.
On Youtube, you can watch videos for the James Kochalka songs Monkey vs. Robot and Wash Your Ass.