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Well first I have a question that may seem silly. Are you using iTunes? If not you will need to start doing so. Apple designs the iPod to only work properly with itunes. There for many other media players may sync the ipod for a time but eventually it will stop working. If so you may want to restore the iPod then attempt to re-sync everything. If this does not work you most likely have a hardware issue. If any of this seems unclear or you need advice on how to perform these tasks please do let me know. :-)
This is common among the 30gb Video iPods. If you play your iPod on a Dock, such as a iHome or other speaker device, for some reason, they like to take the Mainboard out. Normally, if it's a headphone jack, the problem will start with sound only playing on one side of the Headphones.
As a start, you can replace the headphone jack and see if it corrects your problem. If not, you will need to replace the mainboard in your iPod.
I have had the same problem on my sisters ipod. Unfortunately I could not fix it. You can take it down to the apple store and have their genius bar look at it, even though most of the time I know more about ipods than they do they will at least be aware the problem exists. I pulled the hard drive out and put it into another iPod to test it. The hard drive is fine. My best guess is that a transistor or something on the circuit board went bad and is not allowing for that function. What I did was sold it on eBay as broken for $86 bucks. I then went to apple.com/store and scrolled to the bottom left of the page and they sell refurbished ipods that appear new with the same warrenty as a new one. We bought my sister a 80GB classic for $179 minus the $86 we got from the broken one. It was nice to have the new one for less than a $100 total. It's either that or find someone that knows how to replace the circuit board which costs around $70 bucks used. Good luck.
i too had the same prob... try convertin those songs tat are not copied to ur ipod... try convertin them to wav or ipod to play in ur ipod,,, try manually syncin these songs,..it also happens if the audio is in a very bad quality..
It's unlikely you'll be able to get back your songs. However, you can try using poddox (install on your PC and connect the iPod) and see if it finds any of your old songs on the iPod. If that doesn't work, try connecting the iPod to the computer and installing an undelete program such as Free Undelete and restoring files found on drive X, where X is the letter of the drive that your iPod shows up as on windows.
Try booting it into disk mode. Do this by clicking on the menu and center buttons at the same time. When you see the apple logo, immediatley hold the centerbutton and play button down at the same time for 10 seconds. The ipod should now say disk mode at the bottom and have a check mark on the screen.
Then connect it to your computer, and format it using your computer. To do that click on my computer, then right click on the drive letter assigned to your ipod (should be like drive I: or H: or similar.. Then scroll down to format and click on format. This should reformat the ipod completely.
Once that is done disconnect your ipod from the computer and reset it again using the center and menu buttons. After it reboots, try reconnecting it to you r computer and see if it is fixed.