On occasion, for one reason or another, iTunes seems to have a link to a file that no longer exists. Your options are then to either hunt for the file manually, one by one, or manually hunt and delete all the dead ones. There is a handy exclamation point icon that will tell you which are broken, but there is no way to filter for these.
Fortunately, thanks to a bit of logical jiggery pokery, you can use Smart Playlists and a cunning quirk of iTunes to do it for you. Herein lies a step-by-step guide to finding all those annoying broken links.
Step 1 Create a new Smart Playlist with a single Artist Does Not Contains rule. Put some garbage into the search field so it will return every artist. Call this playlist "All Music".
Step 2 Create a normal playlist called "Working Music".
Step 3 Create a Smart Playlist with 2 rules. These are:
- Playlist - is - All Music
- Playlist - is not - Working Music
Step 4 In the All Music playlist, select all and drag it into the Working Music playlist. This is the cunning trick - only music that is not marked with an exclamation icon will be put in the playlist. Broken music will simply not be added.
Step 5 Look in the Broken Music playlist. You should be greeted by a list of all the broken tracks, and none of the good ones. If you keep these Smart Playlists around and just clear out and re-add to the Working Music playlist on occasion, you will be able to remove dead tracks easily.