I don't talk much about pop culture, either here or in real life. But I'll make an exception for those who are very good at their craft, and this sounds like a great combination: Dr. Helen interviews James Lileks.
I've linked to Lileks many times over the years, and his blog, The Bleat is my first read of the day. I've also enjoyed his books over the years. I haven't had time to listen to all of this yet, but if it's anything like the videos he's done on his site and for his day-employer, the Minneapolis Star-Tribune, I'm sure it'll be a good listen.