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. Get Leawo FREE iPod converter ---------------------------------
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For mac: http://search.yahoo.com/search;_ylt=A0oGkl7oaSdKHjQBq_BXNyoA?p=site%3Awww.leawo.com+mac+video+converter&fr=yfp-t-501&fr2=sb-top&sao=1 if you need some step by step guid, you can check this page.
http://www.google.com/search?hl=en&newwindow=1&q=site%3Aleawo.com++user+guide+free+ipod&aq=f&oq=&aqi=