QuickTunes creates random playlists from the tunes in your library based on your preferences.
Now updated to version 1.2! New features include the ability to choose songs by rating, the option to delete the current playlist, and an option to automatically select a new playlist when WA stops playing.
Very straightforward and easy setup allowing for quick and effective random playlist generation. Works excellent for when you are having one of those days where you can't decide what to listen to. Important note: QuickTunes works off of your Winamp Media Library database.... so, make sure to have songs added to the Media Library before configuring QuickTunes.