> He once sat in his basement for an entire month "playing the DRM off" his record collection
What are you referring to here?
He set up two computers and manually played low-res DRM-protected MP3 files out of one and into the other for weeks, documenting the process on BoingBoing. He touted this not only as freedom but "preservation."
Sounds like the analog hole. You play DRM material out the audio port and at the same time capture the input of that and re-encode in a non-DRM format.