Did the songs you're trying to play work previously/is it all music on the ipod? I believe if you plug the ipod into your computer and hit the restore button in iTunes it wipes everything and resets the factory settings. Seeing as jailbreaking it technically voids the warranty, there's no "official" way of fixing it - but this has worked for me in the past. It could also be a problem with your headphones or the headphone jack. Before wiping it, I'd test it with some different headphones to see if that solves your problem. You can also try a reset on the iPod itself by pressing the sleep and home buttons at the same time for about 10 seconds. This doesn't erase anything, but it does reset the device. Since there are so many things it could be, you may want to try the less severe ones first, then back up your music and the like before doing the iTunes factory reset - then bring it in to Apple to let them know that you can't play music.
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