The problem: A 3G 20GB iPod crashes when a certain song is played. It shows the Apple logo, and when it is done restarting, all the preferences are reset but all songs are still there. It only happens with this one album (NOT a playlist). All the songs cause it to crash. Run the iPod Updater from Apple's website and it says that the sofware is up-to-date. Edit: It is my friend's iPod, and it is a Windows sync. But I do know a lot about his iPod (helped to fix it before with something else) and we are in constant contact. The solution: Up to you.