So, I did find another topic about this, but I'm not on the same boat. I did not get these songs from itunes. My problem is this, when I try to import all my audio from a ZFS dataset, it fails. It marks the files as bad even though they aren't. On windows, they will import and work just fine. On linux, it's the opposite. The songs are in an mp3 format.
Should probably include this:
Debian Jesse, 64bit
Mediacenter 20.0.131
Problem solved. I believe a ZFS scrub messed it up.