Chosen Solution
only plays in one ear
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. iPod 5th Generation (Video) Repair iPod Video 60/80 GB Headphone Jack & Hold Switch