Hi MusicBud114,
Welcome to the Support Communities!
Is the issue happening with this one song/album? If so, deleting the song and redownloading it may resolve the issue. I'm also including general troubleshooting steps for the iPod classic for you. iTunes is compatible with Windows 8.
iPod Classic User Guide:
manuals.info.apple.com/MANUALS/0/MA282/en_US/iPod_classic_Features_Guide.pdf
To remove a song, video, or other item from iPod classic:
1 In iTunes, select iPod classic in the source list.
2 Select a song or other item on iPod classic and press the Delete or Backspace key on your keyboard.
If you manually remove a song or other item from iPod classic, it isn’t deleted from your iTunes library.
Downloading past purchases from the App Store, iBookstore, and iTunes Store
http://support.apple.com/kb/ht2519.
The 5 Rs: Reset, Retry, Restart, Reinstall, Restore - page 56 - iPod Classic User Guide
manuals.info.apple.com/MANUALS/0/MA282/en_US/iPod_classic_Features_Guide.pdf
Remember these five basic suggestions if you have a problem with iPod classic. Try these steps one at a time until your issue is resolved. If one of the following doesn’t help, read on for solutions to specific problems.
- Reset iPod classic. See “General Suggestions,” below.
- Retry with a different USB port if you cannot see iPod classic in iTunes.
- Restart your computer, and make sure you have the latest software updates installed.
- Reinstall iTunes software from the latest version on the web.
- Restore iPod classic. See “Updating and Restoring iPod Software” on page 61.
If the issue is hardware related, this article will help:
Apple - Support - Service Answer Center
http://support.apple.com/kb/index?page=servicefaq&geo=United_States&product=ipod
I hope this information helps ....
Happy Holidays!
- Judy
