So I've been screwing around with an idea lately (I know, cheating on my normal lack of thoughts..), and I've never heard it summed up as well as I did here

If you want to operate an internet radio station legally,
  you need to do these things:
 
Follow the play limits and other restrictions on content
    mentioned in the DMCA, and summarized above;
  
Fill out the licensing forms from 
    ASCAP,
    BMI, and
    SESAC,
    and send each of them at least a couple hundred dollars a year;
  
Fill out the webcasting licensing 
    form for
    RIAA,
    and expect them to start hitting you with a large bill some time
    next year.

If you want to do something different, for example, if you want
  to let users choose the songs to download, or you want to archive dj
  sets, or you want to allow the world at large to collaboratively dj
  by voting on what song to play next, or anything at all
  interactive that actually takes advantage of the power of the
  internet: well... you're fucked.  When you go into that world, you
  are out of the ``compulsory license'' territory, and must negotiate
  with all of the copyright holders individually, which is
  prohibitively complicated, since there are so many of them.

Added at *unbreakable numeric code-time* by dave:

One addition to the linked info: BMI statistically samples your station rather than figures it out on their own- you have to fill out a log over a 72-hour period at least twice a year. Kind of fun if you work at a station, since you get to decide who gets paid.

Don't even get me started about "fair use."

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Added at 1012915661 by matt. See Previous