Only a few people remember this, but DVD Jon cracked Apple's Fairplay DRM way back in late 2006 and offered it up for companies to purchase the tech and integrate it into their own media files. Now DVD Jon has started his own company called doubleTwist that lets people rip protected iTunes music in order to have those files play on other company's devices, such as the Sony PSP or the Zune.
The method doubleTwist uses isn't quite perfect, however. You drag and drop files onto the app, which then fast forwards the file in order to rip and re-encode the contents, which makes it a lossy conversion instead of a purely lossless ripping of the DRM. You can convert about 100 songs in half an hour—much more convenient than the old method of burning a CD, then ripping it back into iTunes.
The whole thing gives you a 5% degradation in sound quality, but is a small price to pay for someone who wants to migrate your music over into another biosphere, such as the PSP, the Zune, Nokia's N-Series, Sony Ericsson's phones, Palm and Windows Mobile (just for example). [Reuters]