Let’s get started with the first method to de-dupe your music. In iTunes, choose the File > Display Duplicates menu item, and you’ll see a list of everything in your library that has the same song title and artist name.
From my perspective, though, this isn’t as helpful as it could be. As you can see from my screenshot below, I have a Roger Waters song from one of his live performances and the same song from one of his studio albums.
Obviously, I want to keep both of those, you silly iTunes. If I didn’t pay attention to what I was doing here, I’d delete one of them thinking I was cleaning things up. So here’s what you can do to avoid such a tragedy. To go back to your normal iTunes library view after looking at your duplicates in this way, choose the menu item File > Display All or click on the button with the same name at the bottom of your window.
Then if you choose the File menu again but hold down Option as you do so, voilà! Display Duplicates switches to Display Exact Duplicates.
What this means is that only songs that have the same artist, song, AND album name will be shown. Apple suggests that the best method for cleaning things out at this point is to click on a column header to sort by it, and they also recommend that you use the “Date Added” column as an easy way to see which versions of your duplicates were added when. To insert a “Date Added” column if yours isn’t showing already, right- or Control-click on one of the existing column headers first.
From the menu that appears when you do that, choose what you’d column you’d like to add to your view.
After that, it’s simple to sort and delete duplicated music, and you’re done! You can also use this on some of your other media types in iTunes (like TV shows) by just clicking on them from your Library list before you choose File > Display Exact Duplicates.
That’s great and everything, but that doesn’t seem nearly so useful. After all, how many people do you know who own as many shows as they have songs? If I owned 10,000 TV show episodes, I’d worry about my sanity more than I already do.