I have used these two freeware pieces of software for several years now. They are both designed with radio stations in mind but I have found them extremely useful in the live sound arena. I think that once you've used them, you won't go back to the Windows Media/Itunes players again.
This software gives you essentially 4 playback decks with the ability to see a count up and down. The software allows for each deck to go out individual outs if you desire. You can build playlists, have the next song just load and wait for your play command or continue on. One of the greatest features is that you can remote start the decks via midi or through the game port. This software makes doing live theatrical events an ease due to the programming flexibility.
I have also been able to run multiple instances of the program successfully as well, when in a pinch.
I use this software with a touchscreen when travelling with tracks. It is much more intuitive than finding a mouse and such.