Really Random Music

One quirk with Winamp is that when using the Shuffle feature, you might wind up
listening to the same set of songs over and over again—we’ve seen situations where
out of 500 songs in a playlist, only 200 were played often,
and the rest rarely. This is
actually expected behaviour, since shuffling doesn’t necessarily mean that songs won’t be repeated. You can tweak the Shuffle Morph Rate in the preferences (Options > Preferences > General Preferences > Playlist), but if the results don’t satisfy you, turn off the shuffle feature and instead, click on Misc. in the playlist editor and select Sort > Randomize List for a truly random playlist.