Nano skips downloaded songs

Question

My nano skips all the songs I downloaded in the iTunes Music Store.iTunes plays the songs in my libary but my iPod Nano doesn't play them and skips to the following song!
It's very weird, and I'm about to get desprate!
So if someone could help me?
  Windows XP  
  Windows XP  

Answer 1

Try this:
1. Put the iPod into disk mode:
http://docs.info.apple.com/article.html?artnum=93651
2. Connect it to your computer, and open MyComputer
3. Open the drive representing the iPod
4. Navigate to iPod_Control > iTunes
5. Find a file named iEKInfo
6. Make a copy of it and store it on your desktop
7. Find a file named iTunesDB
8. Make a copy of it and store it on your desktop, as well
***DO NOT DELETE THESE FILES***
1. Click Start > Control Panel > User Accounts
2. Create a new, administrative user account on your computer
3. Log out of your current account, and into your new one
4. Restore the iPod on the new account:
http://docs.info.apple.com/article.html?artnum=60983
5. When you're setting up the iPod in iTunes, remove the checkmark from "automatically update all songs and playlists"
6. Download the free single of the week from the iTunes Music Store (the link is on the lowest left hand corner of the music store's home page)
7. Make sure this file plays in your iTunes library
8. Drag it over to your iPod in the source list
9. Click on the eject button after the song updates (it's to the right of the iPod in the source lists, it's a triangle with a line underneath it)
10. Disconnect the iPod, and try to play the song.
If the song plays, do this:
1. Log out of the new user and log into the older one. Make sure you're clicking "log off" and not "switch user" or your iTunes will not work.
2. Reconnect your iPod to the computer, and drag some of the older purchased music that would not play on the iPod to the iPod.
3. Eject your iPod again, and try to play your purchased music. Also check to see if the free single still plays.