I use DVD Shrink 3.2 to copy the DVD. DVD Shrink bypasses all known DVD encryption/copy-protection (not sure about Blu-ray or HD DVD) and copies the movie to a folder on your HDD. You then get an option of what you want to do with the copied files. I use Nero Recode to transfer these files to iPOD, or Nero Burning ROM to make a playable DVD copy.
Both software packages are easy to use as DVD Shrink works in tandem with Nero when burning DVDs. The only downside is the copy process which can be processor hungry, so DVD Shrink also does a quick scan of the movie before a full copy, then gives you an option to strip out audio files before starting the process (audio as in France, German, etc soundtrack/sub titles).
DVD Shrink is free (do a search on Googlies) and you can pick up copies of Nero on eBay for pennies. The only big downside I found was, watching movies on the iPOD screen. Although picture quality is superb, its a tiny screen, so in my own opinion, you do lose a lot of content (example, an action movie) because of the size. Ive since binned putting movies on my iPOD in favour of using my trusty ThinkPad. I have, however, got a shed load of Youtube copied content on my iPOD (film shorts, comedy shows, music vids and cartoons). You can copy from Youtube straight to your iPOD using iTube (again, a free program which copies and automatically moves content onto your connected iPOD).
Lastly, non copy-protected content can be copied to your iPOD using the iTUNES program. Youll find the copy program below the Advanced tab.