I use a little tool to manage my MP3s called “MP3 tag tools“. It’s quite powerful, it allows you to mass edit some or all ID3 tag fields, fill them from a file name scheme and vice versa (create folder structures and/or file names from the ID3 tag fields). Now when I recently cleaned up my collection using that tool, I noticed that I had about 400 double entries. I just didn’t notice before because the file names were different. Now as this tool tried to rename the files and put them in the appropiate subfolders, it threw error messages that existing files can’t be overwritten.

So I had 400 files that I could safely delete, which I did. Now I had 400 dead entries in the iTunes library (marked with a !) which I wanted to get rid of easily. Apparently, iTunes does not have a function to remove dead/broken/orphaned entries, I’d have to try to play every song from my playlist so iTunes would mark all missing entries and then… then what? iTunes doesn’t even let me sort by the ! column. That’s really stupid.

There is a solution though:

1. Create a smart playlist with the criterion “Artist” is not “xxxyyyzzz” (or some other random string that does not occur as artist in your mp3 collection). Then name this smart playlist “all entries”. This way, we get a smart playlist with all database entries, working and broken.
2. Create a static playlist called “working entries”.
3. Open the “all entries” playlist, select all (ctrl-a/option-a) and drag the selection to the “working entries” playlist. iTunes will not copy dead entries, so now we have a list with everything and another with only the working ones. We need to substract them from each other. This is how:
4. Create a smart playlist with the following criteria: “Playlist” is “all entries”, “Playlist” is not “working entries”. Check that all rules apply, not any rule. And dang! We just created a playlist of broken database entries. In this playlist, select all (ctrl-a/cmd-a) and hit shift-delete (alt-backspace on macs). iTunes will ask you if you want to remove the selected items from the iTunes library. Of course you want to!

Another way would be to delete My Music\iTunes\iTunes Music Library.xml and have iTunes re-import all the songs, but that would delete all the other information too, like number of skips, rating etc. so better not do it.