Not a perfect solution but works for me If you have a list of songs that you like save them to a folder copy the Music Randomizer into the same folder and your songs are randomized. http://download.cnet.com/MP3-Randomizer/3000-2141_4-10849144.html Just make sure as you install this you decline all the bloat ware that comes with it this will only randomized MP3s If you have Flac (only way to go) try this one, again not perfect but the only stop gap I've found http://sourceforge.net/projects/filerandomizer/ I picked the songs I want to hear and copy them in a separate folder then use the randomizer in that folder. Keep the original folder with the songs intact as this program adds numbers to the beginning of the file so you will loose the ability to keep the original album.