Eeeeeek!

So I was using iTunes and it just randomly decided not to play 95% of my music library. I tried removing them and adding them again, and pretty much everything else except for restarting my computer and iTunes just refused to play them! I can do pretty much anything with the files except play them. The songs are totally random, I can't see any pattern. So I was pretty much like WELL FEIN THEN and used Winamp instead (solved the problem), but my cousins refuse to do so. Can anyone figure out why this happened so this doesn't happen to their music?

iTunes is a mac product, case closed. :)

It could be using an incredibly simple algoritm for the random function, so that it loops 5% of the songs, but I doubt it.