Can I bulk delete songs no longer on my hard drive from iTunes?
Ipod Cleaner did the trick.
This link may help you:
http://paulmayne.org/blog/2007/11/how-to-remove-broken-or-dead-tracks-from-itunes/
As already said by ghoppe, if you want to delete files that are present in your iTunes application but do not exist in your hard drive (they have a ‘!’ next to them), you can follow his link.
For what is worth, I’ve had success in the past using Doug’s Script. It’s very easy to use, just copy to your [username]/Library/iTunes/Scripts (if the folder doesn’t exist, just create it), go back to iTunes and in your iTunes script menu, you’re going to have this: