No, I'm not trying to strip digital rights here.  I used Ruckus before it got shut down, and now have a large mass of songs with expired licenses cluttering up my library.  If I could, I would just delete all the media files from the "Ruckus Player" folder off of my computer, but I, being the wise person that I am, merged that folder into my Music Library folder, so that I could have all my music in one place.

Now, whenever I just set my WMP to play random songs from my entire library, it will randomly pick one of the files that has an expired license, and try to get online to find the license.  Is there any way to delete all those old ruckus files in one go, without individually going through my music library and picking them out one by one?

Try sorting your music folder by Creation date (You might have to add Creation/Modification Date to the Columns). Now highlight the files that have that creation date ( corrosponding to the date you mergred the Ruckus files) and cut and move to a new folder. etc

You can use "search" for .wmp files and delete them from there.