I have spoken before of the Randomator, a Smart Playlist I worked up on the work box’s iTunes install, which shuffles through 10 percent of the available tracks that haven’t been played in a while, and after playing a track, replaces it with the next one in the chronological list. (Right now, songs from the third week of August are being inserted into the rotation.)
If this sounds OCD, consider that I’ve inserted manual sort codes into the lot of them, so that the Jacksons, for instance, sort out Alan, Bull Moose, Chuck, Deon, Freddie, J. J., Janet, Joe, Michael, Stonewall, and Wanda, to appear in exactly that order. Unfortunately for my neurosis, iTunes 12.0.1 occasionally ignores the sort code when it adds a fresh track to the Randomator. It’s still there — Get Info reveals it under the correct tab — but at least once a day the code is disregarded, which is how I found Lisa Loeb right under Lisa Lisa and Cult Jam instead of under Hank Locklin. I’ve run this playlist through at least five full versions of iTunes; this is the first time it’s done this to me.