you know iPod can only play mp4 or h.264? make sure your video format is right first. you may need a ipod converter to help you. I'm using leawo free ipod converter. It is free without limitation and easy to use, you may have a try. Inputs: WMV, WMA, AVI, MPG, MPEG, RMVB, RM, RA, MOV, QT, MP4, M4V, DV, DAT, MP3, AAC, etc.
Outputs: iPod MP4 video, iPhone MP4 video, Apple TV MP4 video, MP3, M4A, WAV, AAC, etc. i download this free ipod covnerter from their offical site. ---------------------
For windows: http://www.google.com/search?hl=en&q=leawo+free+ipod+converter&aq=f&oq=&aqi=
For mac: http://www.google.com/search?hl=en&q=leawo+mac+ipod+converter&aq=f&oq=&aqi=
wish help and good luck. and i think this step by step guide may can help you too.