Wired has a how to 'Put Your DVDs on a Video iPod' . Yes you would be breaking the law, but you could always say it was research for an article...

1. Decrypt the DISC Software like DVDFab Decrypter (www.dvdidle.com/free.htm) removes a DVD's copy protection. Remember, this is the illegal part, which is why DVD decrypting software is always a moving target. Should DVDFab disappear, a replacement is just a Google search away.

2. Combine the Video files
Ripping a DVD produces a bunch of cryptically named .VOB files. VOBMerge 2.5 (medlem.spray.se/evilmastr/mainmenu.php) will string them together. To find the movie, look for a series of very large files named something like VTS_07_1.VOB, VTS_07_2.VOB, and so on.

3. Convert the Movie
Use an app like 3GP_Converter (www.videohelp.com/tools?tool=3GP_Converter) to turn your movie into an iPod-compatible MPEG-4 file. Select "Model: MP4, for iPod" as the conversion mode (there is also an option for the PSP). The resulting file is ready for iTunes.