Kevin is having issues with iTunes. It won't open at all. Leo says it should, and that isn't unusual. Sometimes .dll files get corrupted. Try uninstalling and reinstalling iTunes. Will that delete his music? Leo says no. It'll be safe. But Leo says that iTunes is an app that has never really worked well, and over time, it's gotten more ungainly and difficult to use. It really needs to be stripped down and built from the ground up. Alternatives include Double Twist. Media Monkey.