Q: I have just bought a music video on the iTunes Music Store, and I am trying to put the video on my Sony PlayStation Portable (PSP), but my PSP library doesn’t seem to accept it. How can I put it on my PSP?
A: Like its AAC-encoded songs, all of iTunes’ video content is protected with Apple’s proprietary FairPlay digital rights management system. Currently, the only devices and software capable of playing this content are the iPod, iTunes, QuickTime, and Apple’s iLife software for the Mac.
So, despite any video compatibility similarities the PSP and iPod may have, you’ll never get an iTunes-distributed protected video file to play on the Sony device, at least without manipulating them in violation of iTunes’ Terms of Service.