I have the same problem with my DJ 30, and it exists with several different types of headphones.
I am thinking about trying a mono to stereo adaper, where the plug is mono, and the ear phones are stereo. I don't know if it will work or not.
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Step 1: Your trusty iPod has been a close and reliable friend for a long time but one morning only the sound of air comes through the headphones. The likely culprit is a loose or broken headphone jack that is in need of repair. Rather than spend an exorbitant amount of money to have someone fix it you can easily make the repair on your own and have your iPod friend back. Read on to learn how to fix a broken headphone jack for a fifth generation 30GB or 60GB iPod video.
Open the iPod case with a small flathead screwdriver by slipping it under the centerline of the case. You will find a series of clips you have to release in order for the case to open up about an inch. Locate the headphone jack connection and verify that there are no broken wires. Fix broken wires quickly by twisting the wires back together and wrapping with electrical tape. Test the iPod for sound by connecting your headphones to the jack. Replace the wires completely if you find static coming from the iPod jack. Fold a business card twice so that it wants to unfold and slip it into the case over the blue sponge. This creates the pressure needed to hold the jack in place and allow a solid connection. Push the case together without engaging the clips on the side and test to make sure the jack is now working. Try a thicker business card or fold the first one again to get enough pressure onto the jack connection if the first card didn't fix the problem. Press the case fully together until the clips click into place. Use extra care when inserting your headset to ensure the jack remains in place. DigiExpress - iPod Video / iPod Classic Headphone Jack installation http://www.youtube.com/watch?v=MXXgV6YNGkQ
The headphone may be faulty - may have a broken wire leading to the left headphone. Try a different headphone to see if this headphone is OK, if so the the other headphone is faulty. If this headphone is also does not work on the left headphone then the MP3 player phone jack is faulty and either the phone jack needs replacing or it needs resoldering onto the circuit. This is not a job for a Dummy, you need a friend who knows electronics.
This problem is common with a lot of MP3 players. It is caused by excessive movement of the headphone jack and causes the headphone jack has worked loose from the circuit board. To fix this problem the MP3 player needs dismantling and the headphone jack needs resoldering onto the circuit board to get the headphone working properly.
1 May be the headphone jack has not been inserted properly in the headphone socket. Try removing it and replacing it.
2 Check the headphone on any other audio device just to make sure your headphones are OK.
3 Press Menu, go to settings, go to volume limit and see that it is fixed to maximum.
4 OR press Menu, go to settings, go to clicker, press the center and fix it to headphones
If the headphone jack is loose you can try to use the USB headset (If there is one) or Bluetooth. If you wanna fix the headphone jack yourself you can find a very good step by step guide here. The repair service will take about anything from 40$-60$ to repair it.
I agree with Solution 5. The copper pins in the jack that make the connection to your headphone plug are bent in such a way that they are springy and will make a good tight connection to the plug. When those copper connections get worn, they are not so springy and they bend inward causing you to lose audio on one side of your headphones unless you wiggle the plug and find that sweet spot that makes a connection. Then you have to hold the wire to keep pressure on it... it gets annoying.
You can open the case and there are slots in the headphone jack that you can get a hook scribe (like the dentists use) or safety pin to bent those copper connections back out. Don't bend them too far or they will break. You can also pick get a new part for $25 or a used part much cheaper. Once you iPod is open, it's a matter of a couple screws and a ribbon cable to replace the jack. Problem solved!