Music stops playing out of left earpiece

I've had my iPod Nano 5th generation for over a year now and for at least the last 7 months I've had problems where my headphones stopped playing music through the left plug so I've bought about 12 sets of headphones and all of them have eventually stopped playing out of the left side, so I can only guess it isn't a problem with the headphones as I've never had the same pair or brand. I was just wondering if anyone else was having a similar problem or if anyone knew how to fix it because it seems cheaper just to buy a new iPod.

Replace the headphone jack on your iPod.

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Replace the headphone jack on your iPod.

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Your nano is pausing playback when the screen goes dark (Either when it goes dark on its own or when you click the sleep/wake button). The reason for this is that it is not detecting your headset. You may be able to hear music, but the headset jack is not inserted enough for the nano to detect that it is there (or something is blocking the connection). Here are your three options:
Insert the headset jack harder. Most folks find that this solves their problem. If you can see ANY of the silver of the plug when it is inserted, it is NOT fully inserted. You should feel and hear a click" when it is fully inserted.
Clean out the crud in the headset port. If you have tried #1 and it just won't insert all the way, it is likely that you have crud in your headset jack. Shine a light in there. The entire inside of the jack is white, so if it looks dark down at the bottom, there is probably crud down there. You can try blowing it out or using canned air. Just understand that shoving anything else in there to clean it out will be taking your warranty into your own hands! However, I have cleaned mine out using whatever was handy and small enough to fit in there and so far so good. Your results may vary!
Take it to the Apple store. If you have really tried with 1 and 2 and it is still happening, then there might just be something up with your headset port or your headset jack. If it is the headset jack, you can look closely at that and be pretty sure if that is the problem. Try another headset to make sure. If you have worked all the way through to this point and it is still happening, it is time to take it to the Apple store.
i

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Hi gscoops,
Welcome to Apple Support Communities.
You may find the steps in our iPod Troubleshooting Assistant helpful:
http://www.apple.com/support/ipod/five_rs/classic/
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And you are positive the white part of the headset is flush with the body of the Nano?
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This is usually a sign that your headphones are not plugged all the way in. Make sure the white part of the headset is flush with the body of the Nano and no silver from the plug can still be seen.
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Music stops playing out of left earpiece

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