If you’ve collected an extremely large music library over the years or just upgraded your iTunes library to apple’s new iTunes Plus unprotected music files, chances are you’ve got duplicates of your songs taking up your Hard Drive space.
Removing duplicates from iTunes and your Hard Drive is pretty simple but you’ll want to make sure you’re removing the correct files. For optimal and unrestricted use of your music, you’ll want to remove any duplicate music file you have that is a Protected AAC audio file.
To see what kind each file is in your library:
- Open iTunes and navigate to your Music Library
- Right Click(control+click) the columns in the music library and make sure Kind is checked
Now that you’ve show what kind of file each song is, you can easily find and remove duplicates.
- With iTunes still open and at your Music Library, select File & then Show Duplicates
- All music files that you have will now appear in your music library, you can select the duplicate files that are Protected and remove those and any extras that you don’t want taking up your HD space.

As you expand your music library over the years it may be beneficial to repeat these steps to ensure you keep your library and HD space up to date.
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[...] See the original post here: Quick Tip: Remove Duplicate Songs from iTunes [...]
Use fdupes to delete duplicate files automatically:
from the terminal:
fdupes ~/Music/iTunes/iTunes\ Music/Music -r -d
you can get fdupes from darwin ports or fink
I used mDelDupFile from mdecks.
http://mdecks.com/mdeldupform.php
You don’t need to install any sotware just use the form to upload your exported duplicates and you get a file back from mdecks that will delete all your duplicates.
I liked that you don’t have to deal with installs and worry about getting viruses in your computer, and all that…