In reply to arch:
also when putting 'non' itunes files onto an ipod, you need to find a jpeg of the album cover and imbed it to the file otherwise the display of the ipod just shows a grey box with a ? mark when playing.
google images will find the album cover in seconds, right click and copy the image, paste it into the album cover box of *mp3tag and save, then when the file is loaded to the ipod, it goes across with the album artwork.
*mp3tag is a free program for messing with mp3 files - artwork, file names, track number etc
80 gig ipod classic owner here with no itunes purchased tracks at all