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Try resynching your IPOD with Itunes on your computer then try to play again. If that does not work please respond and we can try another option. Also after you synch try the update option on Itunes as well that could fix any problems on the sofware side of your IPOD.
Press and hold the center button while holding down the menu button. This will reboot your Ipod. Check your IPod cable to see if its shorted. If might have transferred a song and crash in the middle of the transfer.
try reseting it. then resyncing your ipod. to reset it, simply push the middle button down, and the menu button at the same time. a few seconds later and the ipod should reset. then sync the song that had the problem onto the ipod and see if it works. (no point in syncing all your songs becuase if reseting it doesnt work you wasted alot of time syncing songs for nothing)
You can reset your ipod by holding down the menu and select (round
button in the center) buttons down for at least 10 seconds. You'll see
an apple logo flash, that's when you stop pressing the buttons. It will
shut off, then back on.
Have you tried holding the select (center) and menu buttons together? This will completely reset your iPod to its factory settings, whereupon you can plug it into your computer and sync your songs back.
I'd recommend restoring the firmware to the latest version as well, even if you had the most current version installed, as this will usually aid with these kinds of software-induced problems.
OK. Not that I know exactly what your issue is but I can definitely see a problem pattern.
Couple of ideas...what are u playing this on...headphones or speakers....change to a different output medium...if you are using the FM transmitter...try it without it...use headphones etc. My thought is perhaps whatever you are playing on is shorted out and possibly sending power back into the ipod causing erratic behavior and/or reboot lockup.
Second...clean the entire Ipod (reset to factory) and connect it to a different computer and transfer just ONE song and play it.
Let me know about how this works out...i am curious about your issue.