For those who want more of a secondary source, but still deep, consider listening to the Literature and History podcast: https://literatureandhistory.com/index.php/episodes/all-epis...

The podcast moves chronologically through western literature. Each episode focuses on a single text, placing it in its historical context. It goes quite deep - e.g. the Iliad + Odyssey sections add up to roughly 12 hours of audio, and the section on Greek drama is particularly strong.

You can really feel that it is a passion project made with care.