I wouldn't personally be able to the do 100 artists, one song each artist method. For me that's a different post. The reason why is because I have songs from movie soundtracks I absolutely love, yet I would never buy a cd from that artist. For example Moby's "Porcelain", All Saints "Pure Shores" and Sugar Ray's "Spinning Away" from "The Beach" soundtrack will all make my Top 100 because I love the feeling those songs bring me, but I wouldn't have those artists in my collection.

If I stick with the "deserted island, these are the only songs I'll ever hear again" idea, then I want songs that take me to all points of my life and for those songs to bring me those feelings back from that point in time. I'm going to have some oddballs on the final list.