Detecting a damaged file

Hi,
I do not know if anyone can help me here - my ipod has one or two damaged files. The problem is, I do not know which. It has caused the Ipod to skip songs (not necessarily when playing the damaged files) to stop playing and even showing the sad face. It is not the Ipod, because it has been replaced by HP (I bought from HP and their service is great). So does anybody have an idea how to scan 8000 files quickly?
Any help is greatly appreciated