So I've been re-downloading some old TSoYA episodes that I think Chris will find enjoyable and I thought I would list them here too.
Swamp Dogg. Soul writer and singer Swamp Dogg's general philosophy towards musical projects seems to be that if someone asks him to do something he'll give it a try, a philosophy that I identify with. (This might explain Swamp Dogg's country album, for instance.) It's great hearing an interview with an interesting person when both he and the interviewer are clearly just having a great time, and I bought one of Swamp Dogg's greatest hits collections on the strength of this interview, a move I have not regretted.
Nellie McKay. I gather that this interview with singer/songwriter Nellie McKay is a bit controversial, with some TSoYA regular listeners finding her wry attitude incredibly annoying, but I found the interview and the live performances (she sings and plays the ukulele) both really enjoyable. Hearing her talk about playing on Garrison Keillor's show was particularly interesting to me.
Bill Withers. Bill Withers was a great soul writer and singer who got sick of the music industry and has been mostly retired and reclusive since the 80s, but Jesse Thorn (host of TSoYA) managed to catch him while he was promoting the documentary 'Soul Power', and it's a really interesting interview. (Jesse reports that this interview was extremely terrifying for him, particularly as Withers didn't hesitate to let him know if Jesse said something Withers disagreed with.)
The vocoder. Dave Tompkins talks about his book 'How To Wreck A Nice Beach' [the title is a mangled version of the phrase 'How To Recognize Speech'] which describes the history of the vocoder, which had its roots in technology designed to protect phone conversations from codebreakers during WWII.
Mavis Staples. Mavis Staples is a really friendly and engaging speaker, and this might be the best interview I've heard with her. The bit about Randy Newman at the end of the podcast is a particular highlight for me.
I should note that Jesse doesn't just interview musicians -- I was just thinking along those lines because of the tours. He also interviews authors, actors, comedians, and other interesting people. I could keep listing episodes but maybe it's simpler to link to one of Jesse's posts where he lists some audience favorites.