Can you update a 5th generation with music from a 4th generation itunes

I know it sounds stupid, but i lost all my music on my previous 60g ipod photo, no backups etc. A friend (who has a 4th generation ipod photo) was trying to update my ipod with his music, he came up with error messages, "not supported by firewire" etc. He has a MAC pc.
Can i do something about it?

The answer of course is YES. But I do not suggest you to do it, as updating your iPod with some one's iTunes = stealing music - a copyright issue.

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