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If the file is corrupt, then it will skip until it finds one that it can play. I had this on some songs I ripped from a scratched up CD. At a certain point, the files are not clear enough for the iPod/iTunes, and will be skipped. This can also happen if you've unplugged without ejecting the iPod first while you were transferring music. I would recommend either playing a different song, or if it is doing it to all of them, put the iPod into DFU mode. You should be able to google that and have no problem with it. It will wipe your iPod, however.
Look in the music folder (top left of the main itunes page). You should see all of your songs there. If they are there, then plug in your ipod, click on the name of your ipod (left hand ide of the screen) and check the box on the main screen that says (manually manage music). Then go back to the main music folder again, and select all of the songs, (you can do this by clicking on the first ong in the list, hold down the shift key and then click on the last song in the list), then drag and drop all of the songs onto your ipod in the list at the left.
If you got the music off of that horrible program lime wire more then likely you just have corrupt MP3s (they are rampent along with viruses on that program).
however if they are legit Mp3s try restoring your ipod in itunes then reloading all the music.
if this still doesn't work try resetting your ipod and then while the apple logo is displayed hold the menu and middle button to get into diagnostic mode. From there pick FlashScan to test the internal memory
if it passes, and the mp3s are fine, it would meen the data is getting corrupted on the transfer of your computer, check for viruses, try and other USB port, or try transferring the songs from another computer
I have the generation one which was developed in 2005 and mine does the same thing. What i do is hold the menu button and center button down at the same time until it resets itself,this should only take nomore than 30 sec. of holding them down at the same time. That should help.