by 
steve24
ANSWERS: 6
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Hook your iPod up to your computer via USB. When iTunes opens, you will be able to see the contents of your iPod. If you are using a PC, right click on the song you want to delete and select the "Remove" option on the menu that pops up. Not sure how you'd do it if you are using a Mac.
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you go in to the library (in the top left corner of itunes)and click on music then you click on the album the song is in you want to deleat then you click ONCE on the song and press deleat on your keyboard you do this for pictures and games (if you have a iphone or ipod touch)
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Just go on to your itunes and delete the songs you don't want then sync your ipod to your current itunes library.
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throw your ipod away..
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You have to RIGHT click the song in the library. And hit "delete"
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Try Duplicate finder 2009 which says to remove duplicate itune files. http://www.duplicate-finder-pro.com/itunes-duplicate-remover.htm
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