So this seems the most relevant place to drop this. I listened to this older episode of the Switched on Pop podcast last night. It's my favorite podcast - it breaks down pop music. But it really goes deep - chord progressions, lyrical content and how it matches up with the music, influences, comparisons to older music and sometimes even classical music, history, etc. It's a great podcast.
Anyway, the one I listened to is from 2016 and it is about bad people making good music. Kinda like this thread. The artists they discuss are R. Kelly, Phil Specter and Wagner. With mentions of other artists too. I think they really nail what we are all struggling with in this thread. I also found it interesting knowing what we know now in 2019 about R. Kelly to hear their take from 2016. I would love them to do a follow up on this episode.
Switched on Pop · Episode
open.spotify.com