iTunes: Deleting duplicate purchased songs

If you buy your music from the iTunes Music Store (or the UK iTunes Music Store)—and I can heartily recommend it—and for whatever reason end up with duplicate copies of songs, you can remove the duplicates as described below.

If the duplicates were created on a particular day, and you are sure than you did not add any new songs on this date, then you can simply order the songs by date and then remove the duplicate songs as follows:

1. This method was tested on iTunes 4.7, but may also work with later versions.
2. First, please back-up your entire music collection. Don’t even go any further until you’ve done this.
3. Find where your music is stored. It will probably be in the Music/iTunes/iTunes Music directory in your home directory.
4. Create a directory somewhere (e.g. on your Desktop) called “DUPLICATES” (or whatever you want).
5. Manually move the duplicate files to the “DUPLICATES” directory on your hard disk. Note: I said MOVE, not COPY.
6. When you move purchased iTunes music files, iTunes automatically updates its database to know where you put them. This even works when you move a file to the Trash. (This may not be the case if iTunes is not running while you move the file, I didn’t test this. Note also that if you empty the Trash, iTunes will still think it has the songs, but will put an icon next to the songs when you select them to indicate that it has lost track of the corresponding file. If you really have removed the file from the computer (e.g. by emptying the Trash), then the song really is gone.)
7. Select a playlist which contains the duplicate songs. If the duplicates are only in your purchased music collection and not elsewhere, then selected the “Purchased Music” playlist.
8. On the Edit menu, select “Show Duplicate Songs”. Order the songs by song name
9. For each pair of duplicates:
   1. Play each song in the pair, to make sure they are the same song (though not necessarily the same file).
   2. Right-click on the first song in the pair in iTunes and select Get Info. At the bottom of this info pane, the path to the file will be displayed. Close the info pane and repeat for the second of the pair. Make sure that the songs are not the same file.
   3. Select the song that is in the “DUPLICATES” directory that you created above.
   4. Remove the selected song from your iTunes library by pressing the Option and Delete buttons together. Answer the dialog that pops up, but I’d leave the “Don’t ask me this again” left unchecked, to be safe in the future. This will not remove the corresponding file from your computer, it will just tell iTunes to remove the song from all your playlists.
   5. Be careful, because iTunes can only identify duplicate songs by their filenames (and perhaps some coarse metadata contained in the file), it cannot automatically listen to the songs to see if they are the same. It is common to have songs with the same name which are not the same (e.g. I have two Portishead albums that have the same song: one is a studio version and the other is a live performance). This is why it is very important to play each file in a pair, and to check the path to the file, before deleting one of them.
10. Once you are sure you have removed all the duplicate playlist entries, you can delete the “DUPLICATES” directory. However, I would leave it somewhere safe for a few weeks, just in case you made a mistake.