Have you collected hefty load of unchecked, unwanted music in your iTunes library? Ever wanted to delete those files from your computer without going and finding each song on your hard drive?
Unfortunately, iTunes' behavior prevents us from A) Searching for unchecked songs, and B) If you manage to create a false negative Smart Playlist of unchecked songs (a clever trick described in this post), iTunes does not allow you to delete them from your library while viewing them in the Smart Playlist.
To add on to the workaround referenced above, in order to delete these unchecked songs, select them all, hit "Get Info," and enter a unique term for the Album field (such as "xDELETEx). This may cause them to disappear from your pseudo "unchecked" playlist, depending on the other parameters in your smart playlist, but this is OK (read on).
Now that your unchecked songs now all share the same unique Album name, exit to your main iTunes playlist, "♫ Music" and do a search for the same term ("xDELETEx", in this case).
Select all your unchecked songs here, and go to Edit > Delete. Depending on your iTunes settings (I have my iTunes library automatically organized— "Copy songs to iTunes" and "Keep iTunes organized" are checked in my Advanced tab in Preferences), you will be asked first to confirm your action, and then a second dialogue box should appear asking if you'd like to keep the files in your iTunes folder, or move them to the Trash. Trash 'em—your overcrowded hard drive will thank you.
From there, you can empty your Trash, or copy the rejected audio files to a USB drive and mail them back to your friend with a note questioning their musical tastes (optional).
