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oldturkey0
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Make sure that you check with another headphone, just to make sure that the ones you have work. You can also take a can of Duster and hold the iPod upside down and spray a few puffs in the head phone jack. If it still does not work, I think it is time to open up the iPod and replace the head phone jack. You can find the guides and the parts on here. Good Luck.
[[Device:iPod 5th Generation (Video)]]
iPod Video 60/80 GB Headphone Jack & Hold Switch
Includes headphone jack & hold switch — 35 available at 29.95 each.