How do I delete duplicate songs in iTunes? No, I don't want to see hundreds of pairs of songs side by side that must be selected and removed one at a time. No, I didn't just add a folder twice by mistake so sorting by date and deleting recently added duplicates isn't an option. It seems like this should be a basic functionality but all I can find is Dupe Away for $14. I'd really rather not go through the bother of finding new media software, how can I delete iTunes duplicates for free?