I bought an iPod Classic back in 2009. A few years ago, the headphone jack failed so I bought a new one before Apple discontinued it. This week, the 2nd one that I bought did the same thing. I'm wondering if Apple would fix both of them at my local Apple Store. Both 160GB. I'm willing to pay a reasonable amount to get them fixed too.
MacBook Pro (Retina, Mid 2012), OS X El Capitan (10.11.3), Late 2009 iPod Classic
Another solution, cheaper and without having to operate on your ipod...
My headphone jack stopped working properly: only one ear works when the phones are inserted all the way in; both work if they're only half inserted, but the sound is quite poor. Well, I just ordered a 'Decrescent Dock Connector to 3.5mm Jack Car Stereo Auxiliary (AUX) Line Out Audio Cable Lead for Apple iPod, iPhone and iPad - 1m' from Amazon.co.uk, along with a '3.5mm Female to Female Stereo Coupler Plug', from Amazon.co.uk: net price less than £5. The dock connector goes into the ipod, the coupler plug enables you to plug your headphones into that. Granted, I've ended up with a lot of wire (maybe shorter doc connectors are available). But it works.
Apple won't do the repair for you. You may find a third party that will, or you can pick up the part and some necessary tools on eBay for a few $/£. I've replaced several over the years and the difficult part is easing the case open while making as little damage to it as possible. You can find videos that explain how it is done.
tt2
You can also use the 30-pin dock connector for audio output. Supposedly provides better quality audio. I saw this on Amazon
http://www.amazon.com/gp/product/B004V9CW7A
I don't have personal experience with this type of product.
iPod Classic headphone jack
