iPod Why will random songs just cut off when listening to them in my Classic?

This has happened on at least 5 separate ocassions. I'll be listening to a song and it randomly just goes to the next song, the time varies, it could be 2 seconds into a song, 30 seconds, etc... The song plays absolutely fine in iTunes, but I have no clue why it just cuts off all of a sudden. Usually I end up having to take the song off iTunes and then re-import it, it's annoying as sh/t. Has anyone else had this problem? It's really frustrating.