To delete an item from your library:
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Click the item to select it and then press the Delete key.
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Click Remove.
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Do one of the following:
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To remove the item only from your iTunes library, click Keep File.
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To delete the item from your computer, click Move to Recycle Bin. The item will be deleted the next time you empty the Recycle Bin.
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Removing an item from a playlist doesn’t remove it from your iTunes library or your computer. Deleting a playlist or folder doesn’t remove the songs from your library or hard disk.
When you delete a folder, all the playlists and folders inside that folder are also deleted.
You might not be able to remove songs from a Smart Playlist that has “Live updating†turned on, because the playlist is continually updated.