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Generally speaking, you'll clean up your iPod with iTunes to erase unwanted songs and add new songs. You have two ways to delete music from iPod with iTunes, and they can be helpful when you want to get rid of the unwanted songs. iTunes provides automatic and manual methods to help you manage the songs in your device. When you are using the automatic way to manage iPod music, every time you connect iPod to computer with USB cable, your iPod will sync with iTunes Music library. If you have your iTunes Music library organized, you can delete unwanted music from iPod with this easy method. If you want to manually edit your iPod music, you can check Prevent iPods, iPhones and iPads from syncing automatically in iTunes by clicking Edit > Preferences > Devices. Then you can manually sync the songs and playlists to your iPod with iTunes. How to Delete Music from iPod
If Itunes failed, I would suggest you plug the ipod to your computer and manually delete the music files. If you running Windows OS let me know if you need steps on how to access your phone from Pc.or go to http://chasms.com/ for any system help
The first way is uncheck the songs you want to delete on iTunes and then sync iTunes with ipod again, then the songs you want to delete will lose from iPod.
The second way is use leawo iTransfer to delete songs from iPod, the way is connect iPod to leawo iTransfer, then right click on the music you want to delete from iPod on leawo iTransfer to choose "Delete", then the music will be deleted soon. However, this tool can only work on Windows computer.
you must "uncheck" songs in your computer, and when it syncs it should delete the unwanted song from your ipod as well. if that dosent work go to the ipod icon in your left side-bar, and click manually manage music