Purchased songs show up on my ipod but will not play!

I am about ready to drive over my ipod with a car! I have the 80GB ipod and it was working fine until recently. For whatever reason, songs that I had previously (as in months ago) purchased on itunes show up on my ipod, but do not play. All other songs (ones that I downloaded from cd's) show up and play. I have tried everything I can think of but it still won't get them to play! HELP!

See this.
iPod does not play content purchased from the iTMS.
If you have made sure that both the iTunes and iPod software are current and have deauthorized and reauthorized your computer, try this test:
1. Deauthorize the computer.
2. Create a new user in the system.
3. Download the free song of the week from the iTMS in the new user account.
4. Play the song in that user account to authorize again.
5. Restore the iPod (using the iPod updater) in the new user account.
6. Sync just the free song of the week and see if it plays on the iPod.
If it does, you appear to have a corrupted iTunes library file, and you should recreate the iTunes library file in your normal user account, and then sync your music back to the iPod and all should be well.
The following articles will help you.
About Authorization and Deauthorization.
How to restore the iPod.
How to recreate your iTunes library.
How to create a new user account in Windows.

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Try Apples 5R's it might help
http://www.apple.com/support/ipod/five_rs/

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Why did a cd i bought show up on my iphone but will not play

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Hey arp986,
Thanks for the question. With the introduction of iOS 7, you can now see your entire purchase history from within the Music application:
Download purchased music to your iPhone - iTunes Store - iPhone Basics - Apple Support
http://support.apple.com/kb/TI126
To play the purchased content, simply download it to your device by tapping the cloud icon.
Additional information:
Downloading past purchases from the App Store, iBookstore, and iTunes Store
http://support.apple.com/kb/HT2519
Thanks,
Matt M.

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Update!
This is what I did to fix both the skipping songs problem and the iPod verifying forever & not able to restore problem (because of iTunes 9):
a) I used Disk Utility to reformat my iPod while in Disk Mode using the instructions here:
http://support.apple.com/kb/HT1363?viewlocale=en_US
and here:
http://www.methodshop.com/gadgets/ipodsupport/erase/index.shtml#backup
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http://support.apple.com/kb/HT1339
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http://support.apple.com/kb/TS4357
Regards,
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Purchased songs show up on my ipod but will not play!

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