Nakedly Examined Music is a podcast about making music: Why do we do it? Why do we do it the way we do it? Mark Linsenmayer interviews songwriters and composers famous and otherwise about specific recordings, which are presented in full on the podcast. 
Podcast (nakedly-examined-music-podcast): Play in new window | Download (Duration: 1:20:40 — 74.0MB)
Chad’s 2015 album Beauty Pill Describes Things As They Are
We close by listening to “The Prize,” a cover of an Arto Lindsay song. The opening music is “A Good Day” by Chad’s previous band, Smart Went Crazy, from Con Art
Learn more at www.beautypill.com. Hear Chad on NPR. Chad talks about making the new album while on display in a museum and his illness and change of style prior to the album on the Chunky Glasses podcast. Here’s the offical, kaleidoscopic Afrikaner Barista video. Here’s the song “You, Yes You” that references Michael Jackson that Chad refers to. Here’s the current band live, including Jean Cook playing the monome.
If you’re looking for more “entry level” rap/ hip hop, have you looked at Doomtree? Given your background, I think you’ll find a lot of the references familiar – which is pretty important for getting into that genre! It tends to be very referential. Doomtree artists tend to use a lot of literary references and the artists tend to be a bit older, which makes the work more comprehensible to middle aged white people 😉
https://www.youtube.com/watch?v=vcpokC2Ewzs
Thanks! I’ll check it out.
Henry Threadgill shoutouts. Arto Lindsay covers. Those are some fine touchstones.