I'm in the same boat as everyone else. I have way TOO many C.D's to even comprehending doing such a thing. I've thought about it in terms of listening to a certain year of music (since I have songs separated by years for my folders on my computer).
One thing I did years ago was put Megadeth's first 5 C.D's in rotation in my C.D player, and then I put them on shuffle. I thought I would let my C.D player to decide what Megadeth's best songs were from 44-1 (Killing Is My Business-Countdown). I remember my brother coming into my room at some point, so around #28, I decided to guess which song would come up. I nailed #28,....then #27,....#26,....#25, and I think maybe even #24. Needless to say, I couldn't believe that I had guessed 4-5 songs right in a row with 28 left in their catalog, and my brother must have thought I was Carnac or Nostradamus. Did I go out and play the lottery that night? No...biggest mistake ever.