If your iPod is exhibiting the above symptom, one of the solutions listed below may resolve your issue. Note: If your iPod is able to play the content, but the content skips while playing, see Troubleshooting songs that skip on iPod for possible solutions.
Update your software
Make sure that you have the latest version of iTunes installed on your computer. You can download it here.
It is also important to ensure that your operating system software is up to date. If you have a Mac, you can update your software automatically using Software Update. Windows users should check Microsoft's website for the latest Windows updates.
Deauthorize and reauthorize your account in iTunes
In some cases iTunes may "forget" that your music is authorized. You can refresh the authorization by deauthorizing and then reauthorizing your computer. To deauthorize a computer:
- In iTunes, choose Deauthorize Computer from the Store menu (your computer needs to be connected to the Internet).
- In the resulting dialog, enter your Apple ID and password.
- Click OK.
You can now reauthorize your computer by simply trying to play one of the songs you've purchased. A dialog box will appear asking you to enter your Apple ID and password. Once you have done so, click Authorize to finish the process.
Restore the iPod
Restore the iPod as documented in Restoring iPod to factory settings. Make sure you are using the latest version of iTunes when you restore your iPod.
Recreate the iTunes Library
Issues with your iTunes Library could contribute to this issue. Try recreating your iTunes Library by following the steps in How to re-create your iTunes library and playlists.
Issues with specific content
Does the issue persist with some of your purchased content, whereas other purchased content plays without issue? If so, there may be an issue with the content itself, and you can restore it from your most recently made backup.
If you have other issues with iTunes Store content, please contact iTunes Store Customer Service.