Open iTunes and click on "Movies" on the left side. Select one movie at a time by clicking once on it then click on the advanced tab at the top and click create iPod or iPhone version. It will convert for a while then you will have 2 copies on the screen of each. Also on your music go to your selection and then click advanced and create mp3 same thing. Your iPod should then sync your purchases. In the future you should setup iTunes to automatically convert go to the top of iTunes click Edit, then Preferences and setup your preferences to determine how iTunes handles the files. Good luck and please let us know how you do!