Restored iPod, songs wont show?

It started off a few months ago when one of our family computers was stolen. My brother primarily used that computer for his iTunes and I used another one (this one) for my iTunes. Once it was stolen, we tried to transfer his songs to this computer, and no luck. It only transferred my songs to his iPod. This didn't bother him because we had a similair taste in music, but now he wants his old songs back. I made seperate accounts on the computer for me and him, and I basically erased all of my songs off of his iPod. The problem now is pulling up the songs that he previously purchased. I signed on to his account, and they didnt show up. How do I retrieve them.
Long story short:
1: My songs replace brothers songs on his ipod.
2: Made seperate accounts for each of us, restored (deleted) his iPod.
3: Signed into his iTunes account, music wont show up.
Any help or links appreciated.

So your brother's songs are still on his iPod? Or not? I am confused.

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