Are your songs id3 tagged? That's what I mean. Give them as much description as possible. With a decent tagger you can tag multiple files at once. I do albums at a time, then just fill out individual details where needed. I also add description/comments.
This same thing can be achieved using the Description function within LW's Library window, however the description is not transferable like an id3 tag is which is actually added to the file itself.