While contemplating the growing sentience of Winamp and discussing the matter with ceph i was suddenly struck by the inspiration for a new game, Winamp Ouija!! :)
A lot of people try to read meanings into the random selections of music players already (i seem to remember some posts from kallah about especially interesting song/skin matches =) but Winamp Ouija is the advanced version. If you're really gung-ho you take 26 or more songs and rename them for the different letters of the alphabet and possibly some punctuation as well. If you don't have much faith in the randomize you can repeat common letters and vowels a couple times. Then set it going, possibly after asking it a question, and see what it spells out.
If you want more immediately amusing results you could instead come up with a good selection of words instead of letters, this is Winamp Ouija - Madlibs remix. And if you're really desperate for a possibly relevant answer right now damn it, you use various phrases instead of words and see which gets selected first, Winamp Ouija - Magic 8 Ball remix.