Anyway, I've listened to my whole iTunes list a few times before. (I also would like to note that, with the exception of a few songs, I enjoy every single track in my music library and don't have a bajillion songs like other people, so listening to the whole thing, while it takes some time, is still doable)

But... I like there to be some sort of order there. So it's not a random shuffle.

I've done sorting by play count... I've also gone alphabetically by song title, album, and artist name, as well as date added, song length, and genre (which didn't work too well since half of my songs are unclassified). But I'm running out of ideas... I'm currently doing a listen through going by song file size, but after that, what? Need opinionz!