I don't know if its cause it's the older model or not but I need to know if I should go and find the type of headphones that come with the ipod originally or if its the ipod. I've seen this happen before and it was also with a classic. They only work when I apply pressure to them and push the headphones as far down as possible.
iPod classic, Windows 7
Are you able to try another pair of headphones to rule out an issue with pair you are currently using? Have you looked inside of the headphone port to make sure it is clean and clear of debris?
Either way, it sounds as if your iPod's headphone jack has suffered some damage and will need to be replaced. You can have pay Apple for the repair services (they don't actually repair it, but swap it out for a refurbished model), send it to a third party repair service and have them swap out the jack for a little less money, or you can even do the job yourself.
Here are Apple's repair prices.
http://www.apple.com/support/ipod/service/prices/
B-rock
OR its not compatibile: Compatibility of Apple wired headset models with iPhone, iPad, and iPod models
My headphones wont work with my Ipod Classic.
