I’ve just found an amazing free way to remove broken songs from iTunes.  I have over 30k tracks in my music collection, so finding all broken songs i.e. those that have a ‘!’ mark next to them is nigh on impossible.  With this clever little trick you can create a new playlist showing all the broken links that you can then either delete, re-import or find on another source….

1. Create a New Smart playlist called ‘All Songs’: Create a rule like ‘Artist is NOT ‘123456789‘ – whatever you choose make sure there is no artist with that name
   
2. Now make a regular playlist called (create playlist shortcut: CTRL+N) ‘All Live Songs’
3. Now create a second smart playlist called ‘Missing Songs‘ with the following rules: ‘Playlist is All Songs’ and ‘Playlist is not All Live Songs’
4. Then select all your tracks in the All Songs playlist and drag them to the empty ‘All Live Songs’ playlist.
5. When you copied all the songs to the empty All Live Songs playlist, only the live songs were copied.

So, if you go back to the Missing Songs playlist that is showing songs that are in All Songs which includes the missing songs, but are not in the All Live Songs playlist which doesn’t include the missing songs, then all that’s left in the Missing Songs playlist are the broken songs!

Update (thanks Paulsuk): To delete the matched files, hold down Shift (or, on a Mac, Option) while deleting.

Thanks to Thilak for an excellent tip.  Definitely my favourite one for a long time.