Users have been experiencing issues with syncing their movies with the iPhone and the iPod Touch (as well as other video-enabled iPods).
Apple Support Discussions user dpman:"I have an MP4 movie on my computer, but I cannot transfer it to my iPhone. It is in iTunes movies, but it won't transfer..." Possible Workarounds
ASD user abellan offers this Apple KB article: Apple KB Article HT1211
Also recommended from the Apple KB articles: Apple KB Article TS1497Check your file type:
Apple Support notes the following--"HD content cannot be synced to an iPod. When trying … Read more