I have about 1000 songs on my itunes but I can only get about 700 on my iPod. They were all on their before but then I downloaded a music video and it too won't go on the iPod. On itunes it has about 4 gb but only about 3gb is going on my iPod. I have a iPod classic 80 gb. How can I get all of those songs on their? A thing pops up when I sync it and it says that an unknown error has occurred (-69). I don't know what that means. Please help me asap. I spent the last 4 hours messing with it and it got me no wherwe

Have a look at this technical document first.

http://docs.info.apple.com/article.html?artnum=302684

My guess is there's something about the movie file you mention that's gumming up the works.

Hope that helps.

Try looking at the directional pamphlet. That might help. Or go to the add/remove hardware on your computer.

Here's a description (http://support.apple.com/kb/HT1210) of what to do when you encounter error -69.

BTW, there is no add/remove hardware control panel on Mac OS X (it's not needed by the OS), so if you're using a Mac you won't be able to do that as suggested by ipodaddict01.