Mp3 format, still cannot transfer! Plz help!

Hi,
I am trying to transfer a file to my iPod. It says it is an mp3 format sound, the file can be played on iTunes, but when i try to transfer it, there is an error saying that "the song cannot be played on this iPod. What do i do?
Plz someone help.. Thanks

I just had this problem as well and spent quite a bit of time reviewing all of the suggestions/ideas/comments, and since I am not that tech-savy I remembered this "suggestion" from the UK show The "IT  Crowd" which was "Have you tried turning it off and on again??" (both devices)
http://bit.ly/18qL7OA  (apologies for short ad on the youtube clip)
It worked!! 

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