Playing Songs just downloaded from itunes store

My brother just got a brand new iPod video and we are using the gift certificate to get free songs. We are able to download them on to itunes library and even on to the ipod. But when I try to play the songs we just purchased the screens comes up like it is about to play the song and then it goes back to the main menu of the iPod. I thought it was the song at first so I used my other iPod video and the song started playing on my ipod, but not on my brother's. Any idea why it won't? I updated the ipod, and restored it. I tried everything I could think of.

If your country's iTunes Store allows you to redownload purchased tracks, I'd delete your current copies of the tracks and try redownloading fresh copies. For instructions, see the following document:
Downloading past purchases from the App Store, iBookstore, and iTunes Store
Otherwise, I'd report the problem to the iTunes Store.
Log in to the Store. Click on "Account" in your Quick Links. When you're in your Account information screen, go down to Purchase History and click "See all".
Find the items that are not playing properly. If you can't see "Report a Problem" next to the items, click the "Report a problem" button. Now click the "Report a Problem" links next to the items.

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