LongPlayer is a program that automatically fills your good ol' WinAmp playlist with music from dynamically created playlists. It tries to avoid you hearing the same songs over and over again, based on the last time a song was played and your song ratings.
This is a great idea for a plugin. Just point it to the directory where your mp3 files are stored, and it will randomly load tracks from the entire directory. You can choose which file types for it to work with, mp3, m3u, etc. Also allows for you to save certain combinations of directories; so, for instance if you wanted it to randomize only from your mellow music, you just add the albums you want containing mellow music, and save that as a playlist. Very functional. You can configure it to work with a song rating system as well (chooses songs based on individual rating). Extremely nice for those who are in to the random play style of listening.