Watch DVDs on your iPod, iPhone, PSP, etc. with HandBrake
If you're a reasonably tech-savvy user and want to rip your DVDs for viewing on a portable media player, HandBrake gets the job done beautifully--free of charge.
So you just bought an iPod touch or iPhone and want to stock it with movies from your DVD library. There are countless commercial utilities that promise to rip DVDs, but I recommend trying HandBrake. This open-source (read: free) utility for Windows (download), Mac (download), and Linux converts your DVDs for viewing on iPods, iPhones, Sony PSPs, and other portable media players. It's by no means new, but I just had to share my newfound appreciation for it.
I recently picked up the hilarious Flight of the Conchords on DVD. I also just acquired an iPod touch (quite simply the coolest gizmo I have ever owned). I wasn't about to pay iTunes for a show I already own, so I fired up HandBrake. A few hours later, presto: New Zealand's fourth most popular digi-folk duo appeared on my iPod.
Note that because most commercial DVDs are copy-protected, HandBrake can't work its magic without a decryption utility running in the background. Rumor has it that DVD43, also free (but Windows-only), works really, really well.