First thing to do is reset the iPod and see if that doesn't clear it up...
To reset your 5th generation iPod with video:
1. Toggle the Hold switch on and off. (Slide it to Hold, then turn it off again.)
2. Press and hold the Menu and Select buttons until the Apple logo appears, about 6 to 10 seconds. You may need to repeat this step.
The above is Apple's instructions. I would add that you want to hold the two buttons a good long time like 15-20 seconds before declaring it a no-go. As it says above, sometimes if it doesn't reset the first try... try, try again.
If that doesn't work, then do a Restore on it. If after a Restore, it still is stuck on Hold, then you may have a hardware problem like a broken hold switch or the little sliding part slipped off the switch inside.
Patrick
