iTunes 12 for Windows: Delete songs, playlists, or other items
Delete an item from your library
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Click the item to select it, and press the Delete key.
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Click Delete [item].
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Do one of the following:
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Remove the item only from your iTunes library: Click Keep File.
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Delete the item from your computer: Click Move to Recycle Bin. The item is removed the next time you empty the Recycle Bin.
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Deleting 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 in it from your library or computer. Deleting a folder removes all the playlists and folders inside that folder.
If you subscribe to Apple Music or iTunes Match, songs you delete from your iTunes library can still be available from iCloud, so you can play or download them any time.
If you can’t remove a song, make sure you didn’t select a song in a Smart Playlist with “Live updating” turned on.