I have just now gotten as far as Hildegard von Bingen.
Stepping back a minute: Since I have skipped mountmccabe listens to a band a day week I have been missing out on crazy music listening schemes. I mean, sure, there have been various occasions but they come and go and aren’t as immersive.
So I am listening, incrementally, to (Western) Classical Music. More or less chronologically by composer's birth. Not every composer, not every piece but I think I am getting a good selection. I have organized playlists by Wikipedia's classifications but I think I am mostly going to ignore those classifications other than as a way to split up playlists.
I started with Kassia, a Byzantine composer born around 805. She is one of the earliest composers for whom we have extant, decipherable scores. So I started with her Troparion of Kassiani. I then went back, mostly, for some (anonymous) Gregorian chant.
This was inspired by a post somewhere noting that the way to get into _____ era of music was to first immerse yourself in earlier eras. Figure out where things were so you can more easily hear the changes. And I can say that the Hildegard von Bingen I am listening to now sounds beautiful and melodic after listening to all Gregorian chant yesterday, etc. and I haven't even really looked into the text and how it works with the music.
If you want to listen along to Medieval music you can.
Hildegard von Bingen
Adam de la Halle
Petrus de Cruce
Walther von der Vogelweide
Alfonso X El Sabio
Philippe de Vitry
Guillaume de Machaut
Jacopo da Bologna
Then it is on to the Renaissance! I am not sure how long I will keep going; the Late Baroque period starts to get ridiculous as we reach composers who were prolific and are regularly recorded today (including Vivaldi, Handel and Bach.)
So I am sticking to this chronology, with clear exceptions. This applies to recorded audio that I choose to play for me for every situation other than working out at the gym. So this does not apply to live music; I am still going to go see Robyn Hitchcock in a few weeks, etc. And I am not going to make my wife, visiting friends, etc. listen according to my terms, even if I am picking the music.