I love to just load a fat playlist of good music into my mp3 player and let random shuffle give me whatever comes.
I've been really bugged, though, because neither winamp or quinamp shuffles very randomly. With both, there were whole groups of songs I never heard, while other stuff songs repeated just about every day (and this out of a playlist with thousands of songs on it).
Anyway, I found a plug in for winamp that really seems to randomly shuffle music. You can also weight songs and artists that you want to hear more often. I haven't tried this out, being willing to take a random sample (and being lazy).
The plug in is
RoboDJ
Dated: 09/12/2002