see this is where i'm not sure how to answer. in my case, i have built an actual music 'library' on a 120GB external hard drive. this is where i keep the hundreds of cd's (organized by genre, artist, etc.) and when i want to bring certain songs/cd's into iTunes, i just drag and drop. this way if iTunes gets wiped like this kids problem was, i have it backed up on the external HD. if you don't do something similar to this, i'm not sure that iTunes will actually allow you to back up your files. (i just use iTunes for a friend's iPod, i don't use one myself). like someone above me said though, you can probably just hook up the iPod and go backwards and transfer from the iPod to the computer. i've heard though that there are problems with doing this because of apple's design.. i guess they don't want all the file sharing stuff to go on. someone who uses it more than i do could probably help, i just know the PC end of things.