Songs not-uploading!

This is a post for a family member of myn who is getting really annoyed with his Ipod. He has a big music collection about 21 days worth of music on and it just isn't uploading them properly. It starts up loading the songs fine then it gets to abut halfway threw B and stops he has tried formating it again twice and has tried google'in it and carn't find any of thing that will help.
So as a last resort i made a thread even thow there is probably countless threads like this so I will say sorry in advance.
thanks.

*BUMP* I no ime really inpatient
But dose any one have a clue?

I got $20 rideing on this

Am not the greatest iPod techie myself - mine has just always worked - but some additional info that would be required for any sort of help might be:

Is this a new iPod? A used iPod he got off someone else?
Which iPod does he have - what size?
21 days worth doesn't really tell us much - how many GB of music does he have vs how many GB available on his iPod?
Is he using a Mac or a Win machine to do this from?
It stops... for how long has he let it sit there...30 seconds.... 10 minutes?
Does it stop at the same place - uploading the same song - possibly a corrupted file it's having troubles with?

Well he has got it to work now I have been away now for 2 days so I couldn't reply.
Any way just to let people no I think it was corrupt files he had the 80GB Ipod classic and it was only 20GB full and it was his from new but the songs had corrupted some how :S